It takes a lot of mental preparation and courage to go on a date in this day and age. You just never know who you'll end up meeting—it could be your soulmate, or it could be your worst nightmare. The following stories are of the latter case, and they may just convince you to stay single for a while...
1. She Booked It
Someone I met through social media asked me out. We had a ton of friends in common, so I wasn’t too worried that he’d be a creep. We decided to meet at Barnes & Noble so we could get coffee and pick out books. We are both avid readers, so it sounded like a good place for a first date. He was crazy attractive and smart, and he seemed really into me. I was super excited.
So, we get there and within the first three minutes, he asks to kiss me. I agreed and it was….Wow. Instant fireworks. All the tingly feelings. We keep talking and things are going great, but then he proceeded to keep getting continuously more handsy. He was grabbing my backside, brushing the side of my chest while his arm was around me, pulling me by my hips into him.
All those things are great once you’re a little comfortable with someone, but not at the beginning of a first date. He kept only wanting to make out, and wasn’t accepting my brush-offs. So, 10 to 20 minutes in, I was starting to feel a little icky and kept saying: "Let’s just keep getting to know each other". He said something like, "I want to get to know you, but in the bathroom".
Honestly, that remark can be taken so many ways, but none of them are good. A pickup line involving the word bathroom makes me want to vomit. Eventually, I said I had to get going to work. He tried to convince me to quit my job and stay with him for the day. He told me we could go back to his place. When he said something along the line of "once we get married, you won’t need to work anymore anyway", I was out.
Nope, no, thank you. I told him it wasn’t going to work. He got super angry at me for "wasting his time" and bolted. By the time I got to my car, he had already deleted me from all social media. I’m still not really sure if he was angry that I didn’t want to do it with him in the Barnes & Noble bathroom, didn’t want to marry him, or if it was because I had a job. Maybe all three. Or maybe just because he was a moron.
2. He Was Off His Noodle
He had a very particular way he liked his noodles cooked—al dente, but just a hair soft. He was obsessed with it and always told me I needed to make the noodles because I tended to hit closer to his desired texture than he himself could. One time, I had gotten off from work, and he had been home all day. I had worked 12 hours and commuted almost an hour to get home.
The first thing out of his mouth was, “I'm hungry. Make some noodles”. He had thrown temper tantrums in the past, and I was too tired to deal with it, so I just quietly went about making his noodles. I don't know if it was my exhaustion or something else, but I didn't get the noodles out quick enough, and they were softer than what he normally liked.
I plated some, seasoned them, put them down in front of him, and went to the bedroom to take a shower and go to bed. I had no clue that I was in danger. I was halfway through undressing when a plate full of noodles suddenly exploded against the wall next to me.
Then, I felt something on the back of my head, and the next thing I remember was seeing the bathroom tiles staining red and the world turning gray. He had his hands wrapped around my neck. I remember him saying, "I will end you if you ever make me soggy noodles again".
When I regained consciousness, he was sitting in the living room again, watching TV as if nothing had happened. I tried to go to the hospital, but he caught me before I got out the door. He blocked the door and said with the most frightening smile that still haunts me, "You're not going anywhere until I get my noodles".
I snuck out later that night and went to the hospital. I had a concussion and a cracked rib. The authorities were called, and I got a restraining order. I had some friends at work get my stuff from the apartment—at least what little was left, as he threw out and destroyed most of my possessions. But that was the moment I knew that this man was psychotic and he would end me.
3. Licky Licky
I met this guy at a coffee place. He was nice and we met for coffee once more and then met for dinner at a bar. We were sitting at the bar, and I had turned to get the bartender’s attention. He leaned over—and did the unthinkable. He straight up licked my face, from chin to temple. I was visibly shook.
So he tried to playfully poke me to tone my "what the heck" face down and I asked him to stop. He then leaned in and whispered, "I'll just poke your sleeping body later"…I made him leave. I walked him to his car and had a bouncer stand by the door and wait for/watch me.
I received several messages a few days later. He was concerned he hadn't heard from me and was going to "stop by my parents later to see if I was ok”. I never took him to or spoke to him about my parents’ house/address. I told him I would call the authorities if I ever heard from him or saw him again.
Thankfully, I never heard from him again.
4. Nothing To Think About
This first date was with a cell phone tower tech. He showed up for our date in an old, worn out—and sweaty—T-shirt. The guy immediately decided he could psychoanalyze me. He told me that I was afraid of men, despite me meeting him in a state park. He also told me he's tired of having steak dinners and ice cream and still not getting a relationship out of it.
He actually said that from now on, he was going to take his dates to the bedroom first—not an expensive restaurant. He told me that I had a lot to think about, and he would give me time. Nope, dude, I didn't have to think it over at all. Then, he told me his wife passed six weeks before our date—just six weeks! How did this guy get so jaded about dating in just a month and a half?
He asked if he could call me. I said "yes", but really I was thinking: "You can call, but I'm not going to answer".
5. Social Media Psycho
I was with some guy for about two to three months. He kept trying to pressure me into telling him I loved him. He would cry because when we discussed children, I was always an adamant "No" on the subject, and he would cry about how we could compromise. It was not something I was willing to compromise on.
I eventually got a nice incentive to end it because I wasn't that invested, and he clearly was. The psycho in him didn't come out until after I ended it. He kept texting me that he was going to "Fight for me", whatever that meant. He also said he wasn't going to give up because he had “basically become [her] dad”—referring to my cat—after three months.
He would switch between begging me to come back and threatening me. I blocked it, and when I didn't respond to his texts, he would message me on Skype. So, I blocked him there, too, then on Facebook, Instagram, and so on. Eventually, he started getting nastier and nastier.
He began calling me fat, ugly, and promiscuous and claimed that there was someone else. I changed all the combinations and passwords in my house because I didn’t know if he had watched me type my pin over my shoulder. He then started to harass mutual people we knew.
He would message my best friend and talk about how he was going to put a restraining order on me and that I should expect something in the mail. He spoke of suing another girl I knew for slander and lashed out at a bunch of people in the same circle. Everyone ended up blocking him as well.
Apparently, his behavior wasn't that abnormal because a few other girls came out of the woodwork stating they had a similar experience with him. It all quieted down after a few months, until not too long ago when he tried to add me on Instagram. I immediately blocked him, and he found my super old Flickr account.
He messaged me on that, saying how he was sorry about the way he acted and if I didn't want him on Instagram, I didn't have to delete my account, yadda, yadda. I never responded; I just deleted.
6. Signs From Above
We went for a walk, got a bit frisky rolling down a grassy hill, and just went at it right there behind a Mormon Church. First, a Mormon spotted us and told us we can’t do that there and just creepily watched us get dressed.
So we went elsewhere, at which point we both complained about not finishing. And the next spot we chose ended with about 30 mosquito bites on my behind, two on my junk, and she rolled over onto dog poop and cried that it was only on her.
"Go get a room," God said.
7. He Didn’t Exactly Bowl Her Over
I was planning a first date with this guy a few years ago, and he suggested bowling. I said it was fine, but that I'd done it once a few years prior, and I was legitimately terrible at it. He offered to teach me, but I said another time. I just wanted to get to know him in a relaxed environment. He suggested we still bowl—minus the lessons—and he could also share in the hilarity of my lack of skill. I was down for it.
I arrived at the alley, and things went downhill fast. The lessons started almost immediately. He told me how to stand, where to stand, and pointed out everything I was doing wrong. He told me I wasn’t taking it seriously, and added this zinger: "I’m trying to teach you for your own good". While he taught me, he never smiled—except when he saw me at the start. I told him this was not the fun, chill night I said I was looking for, and he told me it would be if I took the game more seriously. He was actually angry about the whole night.
8. Plenty O’ Fish In The Sea
I came over before he got home from work as usual. I opened his computer—which I did all the time as I had the password—and he had left Plenty O’ Fish and Cougar Life open and was logged in. I was like, “Dude, what"? I looked at the messages, and he'd been trying to meet up with women near us for a while. I called him, and he freaked out.
He told me he set up the account for a friend. Of course, I knew it was baloney, but I wanted closure and stuck around until he got home from work. This was a bad move. I broke up with him; he took my phone and keys, slammed the door in my face, shoved and restrained me, and did everything he could to keep me inside the house with him.
It was the most terrifying thing because he was way bigger than me, and I had never been so powerless in my life. He was screaming at me at the top of his lungs with the veins in his neck standing out, holding my arms as tightly as he could. I eventually ended up curled up in a ball on the couch, dissociating. I hadn't realized until then how bad he was.
I finally talked him down, and he let me go. I didn't go to the authorities because I was in shock, but I had bruises on my arms and was shaky for days. I found out way later that he'd been charged before and had confined another woman. I wish I had gone to the authorities when it happened to me. If I had, I have no doubt that he'd be behind bars now after his second offense.
The worst part was that I GOT BACK TOGETHER WITH HIM and stayed with this guy for a few more months until things escalated even further. We finally broke up for the last time, and he tried to contact me for YEARS. I still have panic attacks when I hear a man yelling at a woman, and I'm still wary of unknown numbers.
I check his name in the court records every once in a while, hoping he's deceased or locked up.
9. Money Matters
He took me to an Italian restaurant. After we ordered he got a phone call. He makes a small chitchat with the person on the other line. Then he says, “Mom, I know, I ordered the cheapest thing on the menu. Mom! I'm here with my girlfriend. I'll tell you how much the bill was afterward”. Two things wrong with that.
One, it was a first date, and I was NOT his girlfriend. Secondly, he lived with his mom (fine…I can deal with that) and his mom micromanaged all of his money—to the point of calling during dinner to see what kind of money he was spending. It was super creepy and really weird.
I saw him one more time to confirm he was a strange ranger and broke it off.
10. It’s Been A Slice
The setting of this first date was a pizza restaurant. I knew I was in for a bad date when the guy had the audacity to order for both of us. The pizza arrived, and he served me a single tiny slice of wood fired pizza that did not come close to filling me up. He then—before I could ask for a second slice—packed up the pizza and put it in the back of his car.
I excused myself to call a friend to come pick me up, because I absolutely would not let this man know where I lived. It's been almost two years, and I'm still angry about not having more of that pizza.
11. News Flash—I’m Gone!
On 9/11, my ex and I heard about the planes hitting the towers on the radio while on our way to a coffee shop where I was going to work on my thesis. After the second report, I said, "That wasn't an accident". He proceeded to call me "stupid" and rambled on and on about how dumb I was to say that and that, of course, it was an accident as nobody would do that on purpose.
We got to the coffee shop, where they had wheeled out a TV on a cart in the middle of the restaurant so patrons could watch what was going on. We sat and watched. As we were watching the live footage, we saw one of the towers come down. I immediately burst into tears, as I knew I had just witnessed innocent people lose their lives.
I was wondering, “Oh my God, how many people were still in that building”?! Plus, my brother was on a flight when it happened—he was fine—and one of my friends worked in the financial district in NYC. I was distraught. Anyone with any sense of humanity would have been so.
He leaned over and put his arm around me, thinking he was trying to comfort me. Then he said something that made my blood run cold. He hissed in my ear, "You're embarrassing me and making a scene. Stop crying or go sit in the car". That was the moment I knew I was done.
We lived together, so I was biding my time and planning to leave. A few weeks later, I wanted to go out with my friends, and he didn't want me to go because he would get irate when I had any fun. We had an argument, and he pinned me against the wall and said, "I wish I could punch you in the face right now", and then laughed.
The next day I packed my stuff while he was at work. He was broken; the part of him with empathy just wasn't there.
12. Running Him Ragged
I was the cause of a bad first date. I grossly underestimated how long it would take him (I’m a woman) to hike seven miles. I had to call a friend to get the ranger hotline to let them know we would still be on the trail after 9 pm when the gates closed.
By the last three miles, he was giving pep talks to his legs and threatening to eat the frogs that were hopping on the trail. I had to use my phone to light his way because it was super dark and he didn’t have his. Sorry, dude. You were a really nice guy. I didn’t mean to walk you to the point of collapse.
13. She Over Shared
On our first date, the woman opens her laptop and shows me a video of her giving "natural childbirth" in a pool with her ex-partner. She was full spread eagle, and it’s a closeup shot. I could see the crowning head pushing through and everything. Then, the now seven-year-old kid comes out to watch and is like, "Oh, I love this video!"
In other words, I’m not the first guy she’s made watch this. No second date.
14. Festival Of Lies
My friend’s girlfriend had been taking trips to a specific city for months because her mother had been diagnosed with lupus and apparently needed a lot of care. One day, before leaving for another trip to go see her, she broke up with my friend because she felt she “was being a bad girlfriend and couldn’t devote enough time for him”.
My friend took it like a champ and wished her the best. She even left the door open for a possible continuance of their relationship once her mother got better. She spent that weekend texting him about how hard it was to take care of her mother and how she had gotten no sleep because she had spent the night at the hospital.
The whole time my friend was being incredibly supportive and texting her studies on lupus and all this other stuff. A few days later, my friend was randomly checking his Facebook and saw one of those 360-degree panoramic pictures posted by someone he knew who also had a fling with this girl. The picture was taken at a popular music festival that happened to be around the city where his ex’s mom lived.
My friend panned around, and there was his ex, partying it up. Instead of visiting her sick mom, she had gone to this music festival and hooked back up with this guy. He found pictures of her there all weekend which means she was at the festival the whole time. All that texting about being at the hospital was complete nonsense.
He wasn’t even sure if her mom ever had lupus, or if she was just hooking up with this guy for months instead. He immediately confronted her, and her response was just to ghost him. She could have just broken up with him instead of launching a massive campaign of lies so that she could eat her cake and have it too.
15. Drink Up
I met a girl online and we started talking. Everything was grand. She and I texted often and seemed to be hitting it off well. So we meet and start having dinner. Everything is good except she just seems a bit off.
We order a pitcher of margaritas. We each have one and mid-sentence she just stops talking and stares at her hands. Just...looking at them. I ask if she's ok and she says, “Oh, I'm sorry, I'm just really tipsy”. I say “Really? We've only had one drink”.
She says then, “Oh, I've been drinking all day”. Now, I stop and think about past conversations. She texted me a lot saying, "Hey I'm a little tipsy walking home, keep me company”. I start thinking this might be a trend with her. She then proceeds to faceplant into the table. I think she's joking because it was so exaggerated.
I laugh and realize she isn't moving. I tap her and wake her and I call for the check, which was a looooot more than I'd figured. She then asks if I could walk her home. I said I would as she was in pretty rough shape. We start walking more and more and then I ask how much farther. She says another mile.
So we walk some more and finally get to her place. She offers me some water and then asks if I want to stay. I politely declined and she angrily kicked me out. So, that was that. I had to use a GPS to find my way back to my car.
16. A Real Mess In Aisle Three
I met a stranger at the grocery store, and he asked me out for dinner. Dinner didn't go very well, mostly because he spent most of the date insulting me for being a vegetarian. At the end of the night, when we were walking back to our cars and saying bye, he asked if he could have a kiss. I said no. He asked again. I said no again.
He then said, "How about a peck on the cheek?" Just to get rid of him, I go to do that. The guy fully turns his head and kisses me right on the mouth. This was the one thing I had told him I didn’t want. I definitely knew there would be no second date after that. I ignored all future texts. His last one said: "Why does this always happen to me?"
17. He Was A Different Brand Of Crazy
One evening, my boyfriend invited a bunch of people over to hang out by his fire pit so I could meet his friends. I hit it off with a few of his guy friends as we had the same taste in movies, etc. There was no flirting whatsoever. As the last person was leaving, he and I were standing in the backyard by the gate. He grabbed me by the belt loop and pulled me towards him.
I thought he wanted a hug—he didn't. He was unhappy that I hit it off with his friends because now they might “steal me from him," and this was all my fault. I was confused. He had a large stick he had pulled from the fire in his hand. He wasn't pulling me close.
He was trying to "brand" me with the still red-hot stick in a place no one would see. I still have the scar, but I don't have him.
18. Drama King
This is technically a breakup, but it happened on a date. I tried to break up with him in private in the car. He said he needed a pause on the conversation, took us into a restaurant, then proceeded to burst into tears in front of everyone.
The best bit is that a few weeks later, he came into my work pretending that we hadn’t broken up and I had to break up with him again...while he cried...in front of his sister who was my co-worker...
19. He Came To Save The Day
There was one date that stands out as the worst of all, but in retrospect it's kind of funny. I met this guy online and we had a few conversations before deciding to meet up. He seemed nice and normal, but when he showed up to the date he was wearing a full-on costume. He had dressed up as a superhero, complete with a mask and a cape. I was completely caught off guard and didn't know how to react. I tried to go along with it and make the best of it, but it was just too weird. I never saw him again, and I don't think I ever will.
Freepik,stocking
20. Nothing Was Real
I dated a psycho for nine months. He was lying about his career, past life, and even that his parents weren’t really biologically his. He would flip out and cause a scene for the slightest issues.
If I were three minutes late to his in the car, he would start shouting. If we were at a nice dinner with his family and chatting more than he felt I should have with his sister, he would make a scene at the table that was so loud the neighbors would complain.
I had money in my room, and shortly after he moved in, I found it missing, along with some jewelry. I discovered he had pawned them when I found the receipts behind some furniture. He claimed to have cancer in order for me to not go away on business for two weeks.
Meanwhile, I was the sole breadwinner and wasn’t doing anything to give him any doubts, and we needed the money. I found out later that the clinic he was being dropped off at didn’t offer any treatments for anything he claimed to have. After he moved out, I found yellowish makeup, which he applied to look ill.
I put up with it all for longer than I should have and cracked seven months in. I had a fair number of therapy sessions to process everything and had trust issues with future dates and partners.
21. Telling Tall Tales
I got the friend call bail-out one time. The girl had to go to the bathroom right in the middle of the date so I knew it was coming. She kept talking once she got back for a few minutes. Her story was rather impressive, though.
She didn't stick me with the “my friend needs help” act. She told me that a bus crashed, and she had to get back to the hospital because there were multiple deceased kids. That was interesting.
22. She Never Asked
I remember I went out on two dates with a girl when I was in my late 30s. She didn't ask me anything during both dates. She's very expressive and loves to talk. Even during texts she'd send hilarious memes and emojis that matched our conversation. But during dates, she wouldn't ask me a thing about me. That was a red flag that I should have acted on.
She loved talking about herself. There was never a "How are you", or "How was your day", or even "How was work?" Sure enough, when I said I didn't want to pursue her, and that we should just keep it as friends, she blew up at me and called me all sorts of names. One of which was "loser". She also said, "You jerk, I deserve better than you".
I remember just looking at her stunned and thinking this girl had some serious internal issues. I told her that she deserves someone better than me, because I for sure would not be able to handle what just happened. I told her she was overreacting because she's not losing anything, but that she would have an opportunity to meet someone else.
She then started blaming me for things I've never done. Like, "You're selfish, you only think about yourself! You never think about me! It's always about what you want to do!"
I told her, "You're talking to me like we were dating each other for two years! We only knew each other for two weeks!" I felt sorry for her, considering that she seemed like she had some emotional hurt that wasn't resolved from her previous relationship.
23. Scrambling To Survive
My boyfriend had called the authorities and reported me for things he had actually done to me. It was a very interesting and unpleasant situation for the detective and me to work out. The monster popped the ignition in my car and caused it to catch fire while driving down the interstate.
He knocked me unconscious, then accused my 90-pound, extremely sickly self of hurting him, a 300-pound wannabe linebacker. He stalked me on campus, had his friends call my phone constantly, and generally made my life a nightmare until I could switch schools. But he had the audacity to try to say I had done all of this.
24. Good Enough
My first date was my worst date. After an excruciatingly long car ride listening to him discuss his love of clubs and bottle service, we get to the restaurant he refers to as "enough of a hole-in-the-wall for a girl like me”. After ordering he says he needs to check his bank account, followed by him telling me to cover dinner (I'm fine with paying, just maybe ask politely).
Then he, and only him, spoke for the rest of the dinner, explaining how the earth is flat and he is going to be a senator on Mars in 10 years, so any woman who seriously dates him will need to be supportive. Afterward, since he drove, he dragged me to a club.
Upon him uttering, "This is going so well!" I explained to him that it, in fact, was not, given that I had yet to even have the chance to speak. He then asked him to list examples. After saying this was the worst date I ever experienced, he sat down next to me and asked, "So we can be friends who possibly become more?"
I promptly called an Uber. He texted me asking me on a date every day for a week straight until I finally blocked the number.
25. She Was A Little Crazy
I was meeting up with a woman I’d met online. Of course you always wonder if they’ll match their picture. Well, imagine my surprise when a woman who’s eight months pregnant shows up. A fact that all pictures and conversations had somehow managed to omit. We still went out because I wasn't about to dump a single, pregnant woman, but I really should have.
It turned out she was an off-her-meds, extremely depressed pregnant woman with suicidal ideation who proclaimed her undying and eternal love for me by hour one. And just a fun little side note: she was kind of short and so was her dad, who I did get to meet. Their house was on a farm and the whole thing was built to their height. I'm pretty tall and I felt like Gandalf visiting Bilbo.
26. Two-Faced Terror
My first long-term boyfriend had some weird little quirks. Once he got into doing something, he would ignore me, even if he had asked me to be around. Then, when I had plans, he'd guilt me into canceling them and doing something with him. He would try to isolate me to the point that I was almost always with him, and he would monitor what I was doing. He would also look through my phone.
Once, my friend kissed me on the cheek in front of him. He laughed at the time, only to shout at me later. He had different faces for different people. It was a slow build-up; he went from attentive boyfriend to my sole keeper. Luckily for me, one day, he just seemed to lose interest. It was like a switch had been flipped.
It hurt at the time to be suddenly dumped without reason, but I'm glad in retrospect. He was later diagnosed as schizophrenic.
27. Shortchanged By The Universe
I arrived early at the coffee shop because I was nervous. When I parked, I realized I forgot my wallet at home. Mind you, the coffee shop was 30 minutes from home, and we were supposed to meet in 10 minutes.
So I scrounged around in my car for loose change. Found $2 in quarters, nickels, and dimes. I hurried in and bought the cheapest coffee I could. She comes in, confused that I already got something, and orders her own—very gentlemanly of me not to offer to pay with the rest of the nickels and pennies in my car, right?
We sit outside, with the setting sun in my eyes, but I'm too proud to move so the sun is blinding me the entire hour we are there. Honestly, the conversation was pleasant, but at the end, I shifted my weight on this wooden chair I was sitting on…and heard a loud CRACK.
Sure enough, the chair was broken. I know I’m a large dude, but this just had to happen now? I wasn’t surprised when I didn't get a call back from that date.
28. Three Strikes He’s Out
I was on a first date and I told the guy I was working in the field of statistics. He quickly started talking about how that’s all pointless and meaningless. Um, that’s my profession we’re talking about. Later on, he asked how old my cats were, and I answered that they were 10 and 11. His reply? He said, statistically speaking, "they're going to die soon".
At some point during the date, I think it was while we were walking to the car, he blew out a nose full of snot. The guy didn't even ask if I had a tissue, he just turned around, blew it out, and kept talking as if nothing happened. He actually sounded surprised when I told him I didn't feel a good connection with him.
Freepik, stocking
29. Baby, You Crazy
He sent me to pick up a present he got for his friend's baby shower. I went to the store and asked for it, but they said they didn't have an order. I called him and gave my phone to the cashier. After a moment, she gave the phone back to me, saying, "I will not be talked to like that". I was so confused.
She said he was very rude to her and refused to help me, so I left. When I came home, he denied being rude to her and got mad at me for taking her side. Later, he told me I had ruined everything, we wouldn't be going to the baby shower, and that his friend was very upset. I was confused and felt awful, so I called his friend to apologize.
She had no idea what I was talking about. He had lied about the whole thing to make me feel like a bad person, and it made me realize he was gaslighting me during our entire three-year relationship to make me feel crazy.
30. Well, That One Backfired
I haven't had many dates but the worst—and funniest—was from Tinder. The plan was to start at my house as a double date then, and if it went well, we'd split up and go out.
It never got to the last part because he took a dump in my toilet, blocked it with toilet roll, got embarrassed when my friend went in, and left. Oh, and he forgot his jacket in the rush so got one of his friends to come and get it the next day.
31. This Little Fiesta Went Siesta
This was a summer date and it was super muggy out. We got tea and he wanted to sit outside in the sun. He kept going on about engineering and couldn’t take the cue that I wasn’t that interested. The next thing I knew, I had dozed off. I have no idea how long I’d slept for, but I was sweaty and warm and bored. The weird thing is that he kept talking while I napped.
Freepik, DCStudio
32. Rewind The Tape, He Did What?
I was married for 23 and a half years. He was as nice as could be, and an every-day-a-wonderful-day-kind of guy until he got taken into custody for pleasuring himself in an AMC movie theater parking lot—at matinee hour—with children present. What really came as a shock was that he used his company's mailing address on the official report.
With a little digging, I discovered that not only had he been taken into custody before and during our marriage—and never brought it up—but he had been detained by immigration twice, with officers inquiring where his son was. We had no children. I filed for divorce the very next day as soon as the office opened. He ghosted me after that, forever.
33. Dr. Yuck
I ask what he does, and he says, "I don't like to brag about my job, you know the fact that I save lives every day”. He was a doctor, and he said that with no sarcasm. Then he gets angry because he asked me out on a dating app five years before our date and I didn't respond to his message immediately.
I tell him it was an old account I never logged into he says, "Goes to show girls are so fickle…” And the icing on the cake? He admits he actually has strep throat and "I actually shouldn't be on a date right now”. Gross.
34. He Wanted The Full Package
I had met this guy on a dating app and agreed to meet him in a public park. The guy was an unemployed ex-serviceman and clearly had some mental issues, which weren’t super apparent when texting. As soon as we sat down to chat, he told me about his current terrible living situation and asked if he could move in with me and my kids. He offered to watch them for me while I worked.
I said this wasn’t a great idea and that's when he showed his true colors. He got so mad. I tried to explain and said that I didn’t really know him and we had just met. I was so annoyed that he even thought that it was okay to ask as I’m a very protective mom. The whole time he was very pushy and upset when I wasn’t just going along with whatever plans he already had in his head for us.
Near the end of the meeting, he could tell things weren’t going in his favor and asked if I had intentions of even dating him. I told him outright, "no". He again got mad and just left. Not long after that, I got a message from him saying he’d spent expensive gas coming to meet me, and I could have at least done it with him. Charming. Apparently, I owed him something since I wouldn’t provide him with shelter and financial support.
35. Gut Instinct
For a while, I saw a girl I thought I had hit it off with. We were into the same stuff, but something in my gut was telling me she was off, so I broke it off and tried to remain friendly with her. I found out later that she was playing a long con with me and was only pretending to be into everything I liked in an attempt to domesticate me.
I also learned that once I broke things off, she got so angry she smashed a glass against her door, and when her roommate went to sweep it up, she said, “No, leave it. Those are the shattered pieces of my heart”. Safe to say, I have no regrets and have never doubted my gut instinct since.
36. Third Time’s The Charm
In my sophomore year of high school, I wanted to go see a movie with my date. At the first theater, they asked for ID for the first time ever. I wasn’t 18 and couldn't get tickets. At the second theater, the movie was canceled after the AC broke and the heater reached 95 degrees.
The third theater didn't have seats next to each other. She still wanted to watch it, so we sat in DIFFERENT ROWS. Unsurprisingly, there was no second date.
37. She Walked Away With It
This woman and I were having a great first date and ended up getting a little tipsy together and singing karaoke. She tricked me into showing her a ring I had inherited from my family. Somehow, being inebriated and merry, I completely messed up and did not realize she had kept the ring. She then made a fast excuse—like she needed to go get something or something—and left with the ring.
It turns out she lied about everything, even that she was from my city. I’ve never seen her—or my ring—since.
38. Prove Your Love
Not sure if this is psychopathic or sociopathic, but towards the end of my two-year relationship, my boyfriend threatened to throw himself out of the window. We were 11 flights up, and he opened the sliding glass door, with the railing waist-high. I spent what felt like an eternity physically restraining him from going over the edge, or so I thought.
Both of us were screaming and crying. I was finally able to pull him away, and we both fell back, with me crashing into the TV and him falling on top of me. After that, he just stood up, brushed himself off, and said he was never going to take his life; he just needed me to prove how much I loved him. That’s when I realized he was a psycho and was finally able to break things off.
39. A String Of Bad Luck
There's honestly no way for me to say which date is worse. I've had many bad dates, but these really take the cake. I went on a date with someone that seemed normal until she revealed that she was convinced we were all part of the matrix.
Another person I dated was a biter. I had to go to work and see my family with scars and bruises on my neck because she bit and yanked. I thought I was gonna die. And one date abandoned me at a club because I was out of my introverted comfort zone.
I walked home, then ended up peeing my pants because I was wasted and didn't really care as I was going through a depressive episode. So, as you can see, my dating life has never been easy.
40. The Spy Who Loved Her
On our first date, he told me he was in med school, at the university in the town we lived in. This was a red flag as I knew there was no med school at the local university. I thought perhaps he was taking his pre-med classes or something, so I agreed to go on a second date. On this date, he spent an hour telling me how, when he’d finished with his army service, he had worked as a contractor for the army doing "spy" work in Iraq. He added ominously,"If only you knew the things I’d done!"
During the second date, we had to stop by his apartment to pick something up. While we were there, I noticed all his mail was in a different name than the one that he had given me. This made me super nervous, so I "magically" got a text from my work. I told him there was an emergency and I had to go immediately into work and handle it.
After I told him there wouldn’t be a third date, he got spooky angry. I hoped I would never see him again, but then the worst thing happened: I caught him in the bushes outside my apartment. This happened several times, so I eventually had to get a restraining order in the name he gave me. After that, I never saw him again! Thank God!
Freepik, wirestock
41. Slow, Subtle Sicko
It started out with little things like comparing me to his exes, but it was always favorable at first. He seemed overly enthusiastic about wanting to join me in activities and hobbies I did without him. He would force his way in, then pout or make fun the whole time, but it was subtle. He would make legit jokes about my hobbies that I’d laugh off, but it kept getting worse and more frequent.
He’d then put me down, giving me back-handed compliments, and if I caught on and got upset, he’d say, “Joking” with this smile that never met his eyes. One night we were lying on the couch, drinking, watching a game, and just relaxing. We were having a good time when out of nowhere, he said he no longer wanted to live. I took him seriously and started asking more questions.
He shook his head back and forth in a daze and claimed he didn’t say that. Things got much worse after that. They finally came to an end when he choked me in a rage. He said he was sorry, called me, and sent me flowers. Luckily, my sister helped me out. I hadn’t mentioned too much of what was going on to my family because he had slowly been isolating me, but also because I felt crazy.
I thought I was reading too much into his comments, suggestions, etc. When he choked me, I ran straight to my sister. I left him and everything I had at his house and moved on. It took years and dating some more grounded people to get over it.
42. Is That My Ride?
I once was asked out by the mate of some friends. He asked for my number and called to ask me to dinner. He asks if I mind if he picks me up in his work vehicle. I have been in the corporate world for a while so I'm thinking it’s a company car, zero drama. Looking back on it, I realize I should have asked what he did for a living.
The night arrives, he turns up...in a garbage truck. But wait, it gets better. I decide “Ah well, he did ask and I said yes”, so we go out for dinner. I can only assume he was insanely nervous because he proceeds to get inebriated—to the point that he asks me if I can drive the garbage truck home.
Now, this thing has four gear sticks. I can only drive an automatic. So this numpty drove me home, in a garbage truck. Then asks if he can stay the night.
There was no second date...
43. It Wasn’t A Good Fit
She wanted to have our first date at a shipping mall—which I thought was weird. When we met at the mall, she had her toddler with her. I have kids too, so I got it, but a heads up would have been nice. She told me that she wanted to shop for an outfit for her kid because she was doing a Christmas card family portrait later that week.
It was a bit uncomfortable, but hanging out shopping? Sure, why not. Then, she started holding up clothes to me and I stood back and asked her why. She said it was because I was "about the same size" as her ex and he was going to be in the portrait too. She then asked if I would try things on so she'd know how they would look on her ex. I took the clothes and walked off to "find the fitting room". Instead of finding the fitting room, I found my car instead.
I was very glad we drove separately, and I wasn't leaving her stranded.
Freepik, peoplecreations
44. Sweet Jesus, She Was Crazy
I had a girlfriend who was nuts. I got reamed out for two hours because we missed a bus by five minutes and had to get a different one ten minutes later. I was taking a really hard college course and wouldn’t use my phone much during the term or near exam time. She would get upset when I didn’t respond to her texts fast enough.
She wanted to meet five times a week and call me every night for two hours. Once, I was with her at my parents' house, and she wanted and demanded sweets. We didn’t keep sweets in the house, and the closest shop was a 15-minute drive away. She claimed I cheated on her four times because that’s probably how many days I didn’t call her.
When I broke up with her, it got even worse. She threatened to take her life and got my friends to text me to call her back. She made fake accounts to contact me, and I blocked them all. Then, she got new SIM cards to call and text me. I would get prank texts during the middle of the night, and I blocked them all. And then there was the cherry on top...
She slept with my friend in an attempt to get back at me and tried to get with another friend of mine who, luckily, turned her down many times.
45. Playing With Fire
My first date was definitely my worst date. The girl started lighting matches, would put them out with her fingers, then eat the burnt matchstick head.
46. He Had A Killer Sense Of Humor
I went on a Tinder date a few years ago. He made multiple creepy comments along the lines of "you know, you really shouldn’t just meet guys off Tinder. What if I was planning to kill you?" and kept trying to play it off as a joke. After the fourth time making that "joke", I started to feel really uneasy. It didn’t help that he was also just an unpleasant person to be around in general.
So, I texted my friend to call me with a made up emergency, so that I had an excuse to leave. He dropped me off at her house, and I thought it was all good. But that's when things took a frightening turn. He got out of the car and walked right into the house. At this point my friend told him he needed to leave. He said, "Alright, fine, I’ll leave", and then just continued to stand there staring at us.
We then asked him again to leave. He said he’d leave but he wanted me to walk him to his car. Obviously, this dude was acting super bizarre, and I was scared if I didn't just go along with what he said that he might lash out. So, stupidly, I said I’d walk him to his car. So, we went outside and got to the car and then he just stood and stared at me again.
I said bye and then quickly started to walk towards the house. All of a sudden, he very angrily demanded that I hug him. At that point I literally just turned around and ran into the house and locked the door. The guy sat in the car outside for like 10 minutes texting me super angry stuff about how he won’t leave until I give him a hug and a kiss.
After getting no response from me whatsoever he finally left. So, yeah I guess you could say that was a bit of a red flag.
47. Stuck Between A Rock And A Hard Place
I dated a girl in college for two years. It took me WAY longer than it should have to realize she was nuts. While we were dating some of the signs were subtle, although she was very controlling. The craziest stuff happened after I smartened up and broke up with her.
A group of friends and I worked for my college in the summers and were provided free housing on campus as part of the compensation. She had a similar situation in the summer but for a different department. By that point, we had broken up. There was a large rock outside of the building I stayed in. Any time I found myself walking by it, she would be there, sitting on it, crying.
If I walked by with friends, I would get stares from her. There would be times I would walk by with a friend of mine, who is female. Two minutes later, I got a text asking if I was now getting busy with that girl. The building we were living in for the summer was configured in a C shape with a courtyard in the middle.
My room was on one side of the building, and directly across the courtyard was my friend's room. One night, I was hanging out in my room, and I got a call from my friend across the courtyard. They had seen my crazy ex, dressed in all black, hiding in the bushes under my window, trying to spy on me.
I immediately called her and asked what on earth she was doing. She claimed she was at Walmart. Then, more than six months after I had broken up with her, I was at the big spring concert at my college, seeing one of my favorite bands with my new girlfriend, who later became my wife.
Of course, my ex was there too. She came right up to us, checked out my (now) wife, looked at me, and just said, "This is fine. I don't care. This is totally fine," and then just walked away. I don't know what I was thinking for the TWO YEARS I was with her.
48. Just Watch Me
My worst date was at boarding school, on a college campus. We were both straight-edge dweebs, so we went to a party at the student center together. He got bored in about 15 minutes, so we snuck off into the building together. I thought it was gonna be for some, like, making out and stuff? No.
He found a computer lab and made me watch him play League of Legends for two hours while he tried to explain the game to me. If you meet a hot guy and he's single there is probably a reason.
49. It Was Bad From Five Minutes In
I was married for nine years and then got a divorce. I wasn't really ready to start dating, but some friends convinced me to. My first date after nine years was a complete disaster. We met at a restaurant and five minutes, in she told me she ate a sandwich in the car because she wasn't sure I would be able to pay for both drinks and food.
Seven minutes into the date, she advised me that food service was a good field because they rarely look at people's records—even after what that lying boss of hers at Little Caesars said about her. Fifteen minutes into the date, she told me that I didn't need to worry about her around my kids because she’d never be inebriated around them. She felt compelled to add that she might be buzzed around them but never full-on inebriated.
Twenty minutes into the date, she said she liked me because I looked clean. With the last guy she was with, she had hurt her ankle by slipping on some pizza he had on his bedroom floor when they went to get it on together. The pizza on the floor, however, didn’t dissuade her from doing the deed. Despite the urging—nay, pleading—of all my friends, we did not go out again.
50. Bad Romance
I was driving my ex somewhere, and the Lady Gaga song "Bad Romance" came on the radio. I turned it up a little and started singing along. He lost his mind. He started screaming and crying in the car, saying I was sending him a secret message about our relationship. I tried to calm him down and told him it was just a song I liked!
He was convinced that I really thought we were in a "Bad Romance" and that this was a telltale sign of some impending breakup. He was still inconsolable 15 minutes later when we got back to his house, and his parents had to intervene and talk some sense into him.
51. It Was Like Watching A Car Crash
Online, her profile picture was cute. We had about four or five normal conversations before we decided to go to the movies. Now, I hate taking dates to the movies because this minimizes conversations and getting to know somebody in person, but I was like, “She’s cute, what’s the worst that can happen”?
Now, let the record show she chose the time of the movie and what time I was picking her up, so it's not like she had no idea that she had to use the bathroom. The movie theater was about 15 mins from her house. As soon as she got in my car, she seemed intoxicated, threatened to kick-fight me if I tried anything funny. This all happened within the course of 10 minutes.
On the tenth minute she said "pull over," so I did. I couldn't believe what she did next. She got out of my car on a sort of busy highway street and proceeded to take a dump within eyeshot…it was one of those times where it's hard to look away. When my brain registered what was going on I leaned over, closed the passenger door, and drove away.
52. She Only Got A Hug
So, I went on a date with a woman who spent most of her time on her phone. At one point, I even stopped mid sentence to see if she'd notice. She did not. She didn't have any money, so I was buying all the drinks. Then, it just got worse. She started asking me if I wanted to buy some ketamine with her. To top it off, she called her dealer right in front of me.
I put on my coat and started to leave, and she started crying. We talked briefly, and I gave her a big hug and asked if there was anything she needed. She replied with: "Maybe a tenner?" I walked straight out of there. Later, she texted me, asking to see me again. There was absolutely no way I was going to see this woman again.
53. Time To Get Out
It was a typical Sunday evening, and my ex-husband had been without a job for a few years. He was well aware of the fact that I had to approve several dozen employee time cards before Monday so I could submit payroll. I did this every Sunday evening for three years, and the process took about an hour and a half. He also drank a lot and had a very bad temper.
That evening, he had some severe issues with me completing the employee time card approvals after I had spent an hour cooking dinner for him and my son. I was sitting on the floor of my living room because I couldn't afford a couch. As I was eating dinner and working, all I heard was him yelling at me to put down work and pay attention to him.
Before I could say, "I'm almost done, just a few more moments", he came up to me with a full plate of food, took a huge bite of tilapia, chewed it up nice and good, then unloaded it all over my face, keyboard, and all. I was in complete and total shock.
I couldn't believe the man that I was married to would spew food in my face and all over my work. I just sat there in awe and got him out of my life.
54. The Double Date Disaster
So for starters, this was my first date. First date ever. I had no frame of reference for this, but I had just turned 16 and the guy had been cute at school, so the bar was really low. He somehow managed to limbo himself under it.
I didn’t want to go on a date without another couple because I have no trust in people. He had a big friend group and I knew all of them, so he assured me this wouldn’t be a problem. When I got to his house, the person he’d asked to double with us was...his aunt, who he apparently lived with.
She was 21, I was 16, already great. Her date showed up and he was not aware it was a date. He thought they were just hanging out, not chaperoning her awkward little nephew and his new love interest. He was Polynesian. She made Hawaiian haystacks.
He’d never seen those before, but he walked into the house to the scent of badly burned rice because she couldn’t cook. He saved the rice, everything else was straight out of a can, it was great. They hadn’t planned anything, so they decided to throw blades with us in the backyard.
I did better than my date, he was upset, then his aunt nailed him in the behind with an airsoft BB and he was REALLY upset. To salvage things, his aunt suggested we go bowling. I was wearing ballet flats, so I had to wear his weird too-big 2010 teenage nerd socks, which I already had too many questions about that I didn’t want answered.
So we headed out to go bowling, but not before he tried to reclaim his teenage masculinity by squashing a spider on the wall... by kicking it, and kicking his leg right through the wall along with it. His leg got stuck. His aunt had to help him. I was not impressed.
Finally, we get to the bowling alley and walk in and we’re all really good…but then it gets really awkward because the manager is his aunt’s recent ex. So eventually the date ends, and he tries to kiss me in the back seat of his aunt’s car with both the aunt and her date watching. She cheered.
I’d like to say that I didn’t go on another date with him, but this wasn’t even the worst date I had in high school.
55. She Had It Down To An Art
I went on a date with a girl who worked at a well known local art museum. She talked about art in the most technical, plain, boring, dry terms imaginable, and I could barely follow along. I asked questions, and she made me feel like an idiot. I tried to talk about art—which, incidentally, I love—and was again treated like an idiot. Needless to say, there was no second date.
56. She Ain’t Got No Alibi
One day, law enforcement called me and asked if I had gone out on a date with the woman I was seeing and named every dinner and movie we saw together because she kept all the receipts. She was trying to use me as some kind of romantic alibi.
Then, they asked me to check the front page of the paper, and I discovered she had been accused of throwing a four-year-old child out of an apartment building. She claimed dating me proved she couldn’t have done it because she no longer had feelings for the child’s father. It was about then I realized she was a psycho.
57. Taste Test
He stuck his fingers in my dessert, licked his fingers, and did it again!! I ordered a lemon meringue pie and offered for him to try some. He said “no” only to then proceed to say, “Actually, that looks good". Then he sticks his fingers in for a taste. Yuck!
58. She Waited Six Minutes
I was on a date with a woman and it was only six minutes in when she asked me how much I earned. When I asked why that was relevant, she said she had no intention of working once married, so she wasn't going to waste her time with someone earning less than X amount. I’ve now forgotten the amount she gave, but I remember it being very high, and nowhere close to what I was earning at the time.
I said, "I don't think this is going to work, then". She sighed and said I was another broke loser who thought I could get girls when I wasn't prepared to support them. I noped out of there.
59. Time To Hit The Road
I had a girlfriend and her mom discussing methods for disciplining a boyfriend when he would misbehave and how to use it as a good training tool. I was in the room and couldn't believe what I was hearing. She told her mom about something I did that she didn't like. Her mom said she would show her how to do it and demanded I come over and let her injure me.
I'm 6'3" and, generally speaking, a large person. No one was going to lay a hand on me without a fight, so I told her to get bent, walked out, and drove home. I was living with this girlfriend at the time, and I was her ride home. It was an hour and 20 minutes back to our house. I got about halfway home when the call came begging me to come back to get her.
When I got there, she asked me to come inside, and her mom demanded I let her pummel me for the original thing and for driving away. I got back in the car and went home. My girlfriend made it a few hours later after getting someone else to drive her. We never spoke of it again.
I dumped her in my head the moment they started talking about flogging men in front of me and I did it for real about a month or two later after making other living arrangements.
60. A Night To Remember
Back in the day, I was on extended leave and was going through some rough times. So I went to Colombia to learn Spanish. I was out with some guys from the Spanish school and spotted this absolutely stunning woman. I knew I had to ask her out, even though my Spanish was still pretty basic.
So, I went ahead, asked her out, and to my surprise she said yes. One day later, the day of the date, I didn't feel so well but I decided to go ahead, I was so excited. So I went there, picked her up and we went to a nice restaurant. Afterward, we went for a walk on the beach—yep, sounds cheesy but it's true.
Right then, I started to feel really bad, becoming dizzy and all. That’s when it happened. I had to throw up—not normally, but with all the power my body could give. I don't remember lots about it, apparently, I fell unconscious and woke up at the hospital.
To my surprise, my date was sitting right next to me, in training clothes since I puked all over her. She was really worried and just said that we hadn’t had the chance to finish our date. This year, we're getting married.
61. He Had A Temper
I once went out on a date with a guy who I’d met on gay.com. He asked to pick me up, which was fine. He picked me up and proceeded to road rage at absolutely everyone for any reason whatsoever. At one point, his head was out the window screaming profanities at an innocent family in a van, who had not even slightly cut him off. I was so scared.
62. Gaslighting Goober
The guy I was seeing would get out his guns and—with the safety on—point them at me and go "Bang"! When I would jump, he would laugh and say, "That'd be funny if the safety was off. Wouldn't it? Wouldn't it"?
Then, the next day he'd gaslight me and tell me he didn't do anything of the sort the night before. He was the king of gaslighting. It got to the point where I seriously doubted my own sanity because he would deny everything.
63. He Got Gassed
My worst date started as a total high school thing: a girl wants to set up a date at her place while her parents are gone for the weekend on vacation or something. So I agree to it, we're having a good time, everything's going well.
It’s starting to get late, we're in bed together, and she totally passes out. She’s out cold, snoring, it’s like 3 am and I'm still awake. Then, she starts moving around on the bed a little…and she lets this toot rip like I've never heard.
It started and it just kept going....and going. At first, I thought maybe it was her little old dog. It wasn't...then it hits me and oh my god, it’s so rank. I pull up my shirt to cover my nose like a mask and in my mind, I'm thinking what the heck did she eat?
To top it all off, she then made this little noise of relief when it was finally over. I couldn't take it. I slipped my pants and socks and shoes on real gently so as not to wake her. As quietly as possible I walked out, down the stairs, and right out the front door. Luckily, she lived in my neighborhood and it wasn't a long walk home.
Of course, the next day she asked me where the heck I went and why but I didn't have the heart to tell her, I figured it would be too embarrassing.
64. He Loved Radio
So, my date came in, and first thing off the bat said he recognized me from my acne scars. They’re not that bad, in fact, they're very minor. We moved to a coffee shop and halfway through coffee arriving, suddenly, he just jumped out the window. It was a low, large window, so this was pretty easily done. Once he landed on the sidewalk, he legged it up the street.
I sat there in literal disbelief for ages unsure if I should pay the coffee tab or what even happened. He eventually came back. Apparently, he’d recognized his favorite D-grade radio celebrity walking past and just had to go and tell them how much he loves them. He was raving about how exciting this was while I sat there dumbfounded.
Freepik, wayhomestudio
65. Going Nowhere Fast
This chick was crazy hot. She had told me jokingly she had been stalking me on Instagram for a month before hitting me up to make sure I was what she wanted. I just shrugged it off, but then it hit me. We had matched on Match.com two months prior, but she never admitted to it for some reason. I fell for the bait and we slept together on the first date.
Then, she wanted to come over the next day. I thought, "score"! I must have been great in bed. But it was different. She withheld affection and intimacy altogether. I thought, “OK, this might be something real for once. I'm an adult. I can roll with it”.
Then, she came over the following day and the next. Suddenly, two weeks had passed, and she was leaving half her stuff at my house, taking up all my time, without any show of affection. She told me I needed to be careful not to break her heart because her ex-boyfriend forced himself on her in her sleep for two years, and she would take her life because she was so fragile.
I told her we needed to either be intimate with each other or if not, slow things “waaaay” down. We could go on dates on the weekends until she felt comfortable, but she couldn’t move into my place. She never talked to me after that. Not once. I shipped all her stuff in a box to her mom’s house where she lived, and she never once texted me or replied to anything.
66. Three’s Company
I’m taking a girl to the movies and she asks, "Can my best friend come too?" There goes my chances but trying to be nice, I say, “Of course you can!” She shows up with her friend, who is indeed a guy.
This is when I find out that it’s her one and only ex, but they remained best friends and nothing is happening between them. I think, “Well, this date is ruined, but let’s try to salvage it". I go to pay for our tickets (mine and hers), even when she offered to pay for hers.
After buying, she turns around and buys her ex’s ticket…We actually got along fine and they were nice people, but it was like a tug of war for the rest of the night fighting for her attention. Of course, I lose since they are best friends.
When I get home, the guy adds me on Facebook, and he proceeds to tell me don't bother trying to date her, she's a terrible girlfriend. I finally got her alone for one more movie, but it all just sort of fell apart. I actually really liked her, but clearly, I had no effect on her. Oh well, I guess.
Take note, future daters: movie dates are a bad idea.
67. Free Tats
I started talking to a guy over Facebook Messenger who was a tattoo artist about to open up his own shop. He invited me to come chill at the shop while setting stuff up. I hadn't even been there five or 10 minutes when he started questioning if I told anyone I was there, or where I was going. And if this wasn’t weird enough, it was about to get weirder.
He started asking what tattoos I wanted next and offered to give me a free tattoo right then. And then he tells me that if I'll be his girlfriend, he'll give me all my tattoos for free. I came up with an excuse to dip out fast. It was so bizarre, this dude was a seriously good tattoo artist. I kind of kick myself for not getting the free ink when I had the chance. He was pretty attractive, too. If he had not acted like a creep straight off the bat, he would've had a very decent chance of scoring.
68. She Cashed In And I Cashed Out
I had been talking to a girl online, and we agreed to go out on a date. I showed up to pick her up, and she walked to my car while on the phone. She got into the passenger seat, and I started to drive to the movies where we were going. She was in the middle of a tearful conversation with her estranged father and put her finger to her lips to let me know to be quiet while she had her conversation.
We were 15 minutes away from town, and she stayed on the phone the entire time. She was working him for money to bail her out of a situation. She was making amends with a father she had cut out of her life seven years ago so he could wire her some cash. She put him on mute for a moment to ask me if I could stop at the Dollar General in town so she could get some kind of Green Dot card or something.
Having never officially even talked to this girl in person before, I agreed. I parked at the Dollar General, and she ran in to get the card, came out still talking to her father, gave him all the information while on the verge of tears, and even squeezed a few out for effect. She told him she was glad to have him back in her life once the card was filled with money.
She told him she loved him and hung up the phone. As soon as she hung up, she started to call him names, and as she did, she told me, "I can't stand him". She proceeded to put the phone away and cheerfully apologized for the awkwardness, and went on as if nothing had ever happened.
69. Clownin’ Around
Perhaps not my worst date, but definitely the weirdest. I was on a date with this girl who seemed great: good-looking, funny, shared similar interests. It was our first date, and we were sitting in some bar that she's a regular at, discussing ourselves when it starts getting to the basic first date questions.
"So, you said you work in an office but is that what you really want to do?" I asked, "Did you go to school for it?" "Actually…” She says, reaching into her bag, "I'm currently going to clown school”. I kid you not, this girl had pulled out a red freaking clown nose and put it on.
Now, if this was our third date, I would have been less shocked. However, we had been talking for a week and this was the first date—we were supposed to IMPRESS each other. But she was good-looking, and I wanted to hook up.
So I said, "Oh! That's so cool. I didn't know clown school was actually a thing”.
"Oh, no, it's competitive!"
"I had no idea. So, are you in clown university, clown college, clown technical school?"
And then she took my joke as an attack. For a clown, she had a terrible sense of humor.
70. On A Scale from One To Ten: You Suck
There was a guy who I was considering hooking up with. That is, until he said the following: he told me over and over again that I was a solid 7.5 out 10—at best. He said this was okay because most guys lower their standards as they are typically only requiring a six and above for marriage potential. Yeah, I was done after I found out he wasn't joking.
71. Quaking In Fear
I had a seizure, and when I came out of it, he was standing above me, yelling and cursing at me, saying, “This is embarrassing". Then he dragged me up to my feet, slammed me against the wall, and bellowed at me to never do that again. That was the first indication he ever gave me that he was capable of something like that, and I noped right out of there.
72. Equality At Any Cost
I went on one date with a guy I wasn’t physically attracted to because he seemed nice. He spent the ENTIRE date bragging about how much money he made. We shared a pizza. I had one slice, he had six.
When the bill came, he said he’d appreciate it if we split it evenly “because that’s how things work these days”. He tried to make out with me when he dropped me off at home and my god, his breath... it was like he ate a dead raccoon.
73. Temper, Temper
I was on a first date with a guy, and things were going okay. I went to the bar to get another drink, and the bartender wrote a CD recommendation on a piece of paper for me. When I got back to our table, my date said, "Did you just give that guy your number?" I was shocked and told him, "no", and that I’d just swapped music recommendations with him.
The guy got super angry and said that he was going to knock the bartender’s block off. I couldn’t help but make a comment about this guy’s bad temper. He agreed with me and told me about a time he got so angry while in traffic that punched his fist through the windscreen. He had scars to prove it. That was a big nope.
74. False Positive
When I tried to break up with my girlfriend, she decided she was pregnant. There were lots of red flags beforehand, but that was really the icing on the cake. She would send me pictures of positive pregnancy tests but refused to take any tests while I was there. We made a doctor’s appointment to confirm, and she canceled it behind my back.
She was also pulling the whole “taking her life” schtick while this was going on. I should have known better, but I was young and stupid. It turned out she pulled all of this on her next boyfriend when he tried to break up with her. He got her Baker Act-ed.
75. Got Milk?
A few years ago, I went on a coffee date with a nursing student who described in vivid detail how he and his ex-girlfriend milked an old lady into a toilet at a party. According to him, that was not even the first time or party where he had milked her, he just happened to do it with his girlfriend that time.
I was mortified and found an excuse to promptly leave. The funniest part was a few days later when he texted me asking to go on a second date—which I ignored—followed by another text the next day that said, "It was the milk story, wasn't it?"
76. He Was Honestly Quite Scary
It was our first date and we met up at his place because he was making dinner for me. We were chatting on the couch when he stood up to excuse himself to the restroom. As he was walking away, he turned and mentioned that there were cameras all over his home, so "don’t take anything". I guessed this was a joke, but what he did next sent chills down my spine.
He pointed to a stack of papers on an end table. "I believe in honesty. That’s my arrest record. Everything is right there". He went on his way. I considered leaving right then, but didn’t. I did pick up that stack of papers. It was a shocker. His arrest record was several pages long and spanned three states. Most of the arrests were for domestic assault. There were also some minor drug charges.
He returned and, thank God, my phone rang. I answered it even though I didn’t recognize the number. I actually had no idea who it was. I made it sound like it was one of my daughters and she needed to be picked up from somewhere immediately. I’ll never know who was actually on the other end of that call, but I left this guy’s home and never looked back.
77. I Wheeled Her Out Of My Life
My ex-girlfriend would have rapid cycles of hating me and delusions of things that didn’t happen and loving me unconditionally. The straw that broke the camel’s back wasn’t even that bad, but it was stupid. One day, she called me at 6:45 am and told me how she was parked halfway in a handicapped parking space, and someone had come up and knocked on her window to tell her that.
All I said was, “You can get a $200 fine if you obstruct an accessible parking space”. Her response was, “YOU ALWAYS TAKE THE OTHER PERSON’S SIDE. You hate me. You’re the president of the I hate [her name] fan club. I can’t talk to you about work, ever”.
All this was over my letting her know what can happen if she obstructs a handicapped parking space. Safe to say, we discontinued our relationship about three minutes later, as it wasn’t the first crazy thing.
78. An Awkward Introduction
I got stood up at a cafe. She called and told me an emergency had come up and she wasn't going to make it. I had only been waiting for three or four minutes and wasn’t too upset about it, so I called a friend to see what he was doing.
I ended up meeting him across town at the bar he was drinking at, which is also where he introduced me to my date, who he had just met playing pool there.
79. Her Dance Card Was Full
I was set up on a blind date with a woman who possibly had some issues mentally. When I got to her home to pick her up, we sat around in the living room before we left for dinner. Unfortunately, all she did was talk about her boyfriend who, two years previous to our date, had lost his life in a car accident. Apparently, he’d been driving too fast and was over the limit to operate a vehicle.
After telling me about the accident, she excused herself to go get something. That's when the date turned into a creepshow. She came back with something that had belonged to the guy. Something she had kept to remember him by. To my horror, it was a blood soaked book from the day of the accident. It was very creepy. Even though this was a huge red flag, I decided to go ahead with the date.
We went to the restaurant and sat and talked and enjoyed our meal. Our meal was about midway through, and we decided to pause and enjoy a dance together. After we returned to our table, some stranger came up and asked her to dance, and she said yes, which surprised me, but I decided just to be chill about it.
An hour later, she hadn’t come back from dancing, so I just got up and walked out. I figured she was having more fun with him, so he could give her a ride home. I think it took her a long time to notice I was gone. Looking back, I could have handled that better. And I don’t like how many times I’ve had to say this in my life: "Could’ve done better".
80. Power Hungry
Once, we were talking about kids and how he wanted to have some at some point, and I definitely did not. He said that the reason why he wanted to have kids was because of the way kids revere their parents, and he just wanted to have that kind of omnipotence. He also said kids are great when they are young because they're so gullible.
He said you could make them believe in anything, and he couldn't wait to tell his future kids all kinds of lies and have them believe them. He just loved the idea of having that kind of power and control over other people. It was sick and seriously disturbing that the only reason he wanted children was to warp their minds. We broke up; he's now married with two kids.
81. An Icy Encounter
Back in college, I was invited to an ice rink with a girl I liked and some of her friends. I did not know how to ice skate and I did not pick it up very quickly, but I wanted to try and impress her somehow. Well, I hugged the wall the whole time and made a fool of myself.
The highlight was when I saw a flash of light as I fell in front of a group of people. Turns out I had fallen right at the moment someone took a picture, so my failure was immortalized forever. She took me back to my apartment and ended the relationship before it began. But there's a silver lining.
The woman who is now my wife was at that ice rink on that night. We didn't realize we were there at the same time until a year or two into our relationship and she exclaimed, "You were that guy who couldn't ice skate! Yeah, she didn't seem that into you”.
82. She Had Two Choices
This happened when I was in college. I was hanging out with this guy in a state park during the night—I know it was a terrible idea. It was going alright until out of nowhere he said: "Don't you ever have the urge to hurt people in very bad ways?" Imagine being with a guy in the middle of the night in a park where nobody is around you and suddenly you hear that. Yikes!
So, suddenly, I wanted to get away from this guy. But there was one big problem: I didn't know my way back to the dorm room. I asked him to help me, and he said he wouldn’t. He gave me two choices: I could figure out the way back by myself or I could spend more time with him in the woods. He then took my phone, so I wouldn’t be able to check the Maps app.
I can't believe how naive I could be sometimes when I fall for someone. I am so glad nothing bad happened.
83. Post To Post
I was really young and innocent at the time. My boyfriend started posting all of my information online. He put my full name, address, and a bunch of other information out there for people to find. That was already pretty bad. Then, he started sending me pictures and videos of him self-harming and swallowing entire bottles of pills.
That’s when I knew I needed to get away from him.
84. Bragging Rights
On our second date, he bragged to me: 1) how long he was able to stay on unemployment, 2) how he was always able to talk his mom into letting him come home after she kicked him out, 3) how he basically paid for the $3,000 implants of a dancer, even though he didn't get anything for it.
He also revealed that he got locked up for about four months for pulling a pistol on some teenagers, but he didn't intend to use it. This was a half-brag, not a full brag. It was so strange because he seemed like a nice guy on the first date.
On the second date, with all of that, I was just laughing inside and wondering how I was going to end the date. Turns out it wasn’t a problem because after dinner he had to go and hang with his buddies at the video store.
85. Stamp Of Disapproval
Years ago, I went on a first date with someone I met online. We met at a bar and the bartender carded us. Even though we were both older, they were still doing stings in the area, so he was carding every single person. I handed mine right over, but my date was a real jerk about it. The bartender checked mine and handed it back to me.
Then, he checked my date's ID, and rather than handing it back to him, he placed it on the bar right in front of me. When I saw it, my blood ran cold. It had an "intimate" offender stamp on it, which is a thing in my state. The guy picked it up, looked at the bartender, looked at me, and then got up and walked out. I immediately Googled him.
He was on the registry and had been in prison. Lesson learned. Always Google. And that bartender? We’re still friends.
86. Long Distance Looney
I was in a long-distance relationship, and my girlfriend banned me from watching lewd videos. At one point, she got so serious about it that she forced me to install remote access software so she could randomly remote into my computer and make sure I wasn't watching anything behind her back.
This extended into my social media, where she would randomly log in to my Facebook and scour my messaging history to ensure I wasn't cheating on her. I'm so glad I got out.
87. Laying All Her Cards On The Table
My worst date? She had Crohn’s disease. She takes her pee bag out in the middle of our dinner date and says I need to look at it so I understand what I’m getting myself into. The catheter tube knocked over her drink. It was awful. Poor girl.
88. Showing Off His Creepy Side
I once browned out at a club and remember briefly meeting a guy in a suit. The next day, I woke up to a text from Willis, the guy in the suit. Turns out we both didn't really remember each other. Over text, he seemed nice enough and we both thought it'd be a funny experience if we went on a date.
We met up for lunch and upon meeting him, I didn't really have much hope for a second date. He was kind of awkward and tried a little too hard to stunt. But whatever, he seemed like a nice guy. We sat down for pizza and started getting to know each other.
I told him I was studying public policy and was delighted when he asked what kind of policy I wanted to focus on (most people don't really care). I went on a whole rant about how much I wanted to make education policy better because I thought education had the potential to dramatically change lives, especially for those not born into much.
After I finished my rant, he says, "That's cool but I don't really believe in education for low-income people because when I grow up, I want maids and butlers and, like, someone has to do that”. I responded, "Some people have that viewpoint," and started to look for ways to end the date. But the worst was yet to come.
After we finished eating, I made up an excuse to leave an hour earlier than planned. He asked if I really had to go and said, "I should just kill you and keep you with me”. Smooth. I told him he probably shouldn't joke about that. He responded, "I would bury your body right there haha”.
I hailed down a cab after that.
89. Momma’s Boy
For our first date, he took me to dinner at his mother's…with his brother and the mother’s crazy housemate. After dinner, we watched Iron Chef with all of them while sitting on the floor because there weren’t enough chairs. During the show, his mother was talking to us about using vibrating toys when doing the housework to make it more enjoyable.
And here’s the best part: He didn't even live with his mother. Needless to say, it was our first and only date.
90. I Made A Quick Departure
I was traveling, and when I landed in Boston, I was immediately hit with a barrage of texts that grew increasingly agitated. They started with "Hey" and ended with, "WHERE ARE YOU! DO NOT IGNORE ME"!
I texted back, "I was on an airplane. Remember when you drove me to O'Hare THREE HOURS AGO"? We had only dated for a few weeks, and there were signs, but that was the red flag I needed to call it off.
91. Musical Urinals
We went to a movie. During the movie, she got up to go to the bathroom. After she left, I thought I could run to the bathroom myself, and be back before her (for some reason, I thought it would be rude to leave her alone). When I came back to our seats, she was already there but I didn't give it much thought.
I hung out at her place for a bit afterward, gave her a kiss goodnight, and went home thinking that I just had a pretty nice date. A week later, after she wouldn't return any of my calls, I asked our mutual friend who introduced us what the deal was. Turns out that when I went to the bathroom, I accidentally walked into the women's room.
I peed in the stall next to her, and she recognized the boots I was wearing. She thought it was the biggest red flag of all time—and I can't really blame her. When I finally got a hold of her and tried to explain myself, she told me she was moving to Turkey to get back together with her ex-boyfriend.
92. Scene And Heard
I needed to catch a bus. The entrance of the university to the bus stop was a mile away. I was breaking up with my girlfriend in public to make sure she would not make a scene, but it totally backfired. She made a huge scene and begged me to stay with her, but I refused. She stalked and followed me, begging, crying, and yelling in front of around 30 strangers.
Once I got to the bus stop, she tried to push me in front of a running bus. I yelled at her, "Are you trying to kill me"? She responded, "I want to if you are not with me". Then, she proceeded to break into my house. She filled it with photos of us.
Later, she called me several times, screaming that she was going to take her life. Then, she tried hitting on my friends and managed to make out with my ex-best friend.
93. The Ole Switcheroo
My worst date started off as a date and ended up as an MLM pitch. On the plus side, I still have those Cutco scissors and they are decent.
94. Outed!
Waited for her at the theater for two hours. She shows up drunk. Watched a terrible movie, just whatever was about to start. She took me to a bar afterward. Ended up being a gay bar and she tried to get me to admit I was gay. I flirted with the gay bartender to make the night less awful.
95. Eat And Run
I went out to eat at Buffalo Wild Wings one night with a few friends, and I told my girlfriend about this. I saw a couple of her friends come in and sit at a table near us, but they never ordered anything. They just drank water and sat there, occasionally glancing at us.
After my friends and I were done eating, we walked outside, and sure enough, I saw my girlfriend’s car in the parking lot. Her driver’s seat was reclined all the way back, and I could just barely see that she was in the driver's seat, trying to hide. I was already kind of weirded out at that point, so my friends and I were going to leave.
As soon as we backed out, her car started and backed out as well. She began to follow us through the parking lot. I began texting her, asking her what was going on, but she kept saying she was with her mom hanging out. I ended things shortly after that.
96. The Stench Of Success
It was my third date with a girl, and we went to a Poison-Def Leppard concert. We weren't eating before the concert and I was starving, so I grabbed a chicken salad sandwich from a gas station before I picked her up.
Halfway through the show, I have to poop. Bad. I run to the can and every toilet is knee-deep in filth. We had VIP seats, so I figured I would wait and hit the VIP bar on the way out. I took a massive dump and made five guys scream about the stench, which made me giggle.
Well, we parked in front, pulled the car out, and sat and waited. All of a sudden, round two hits—and this time it is wet. I was getting stomach contractions every 2-3 minutes, I was death-clinching the steering wheel and sweating like a fat lady in Golden Corral.
I then had an epiphany that if I just tooted a little, I would feel better. Oh, how wrong I was. The soft serve ice cream machine in my shorts exploded and got everywhere. I ran into the woods, finished pooping, and wiped my butt with my wifebeater.
We have been married 12 years now and have three kids.
97. Eating For Two
I chatted a girl up online for about a week or so, and things went pretty well, so we decided to meet up. I asked her out for dinner, and said that if things went all right we'd go grab a drink. Let's just say her photo didn't match her appearance. Her excuse was that she had a crazy ex who was stalking her, so she used her sister's photo and name.
HER NAME!!! SHE LIED ABOUT HER NAME! Anyway, come to find out through our "interview" that she was an only child. She didn't catch her slip up, but I sure did. She rambled on and on and on about stuff I really couldn't have cared less about. Then came the food. The waitress may as well have brought it out in a trough, as this woman didn't use her utensils.
Did I mention we were at a steak restaurant? That's right folks, she picked her steak up and ate it with her hands. Let's not even get into the potatoes. It was the worst date of my life. I couldn't eat my meal. I told her I wasn't feeling well and that I was just going to get my food in a box to go and I'd eat it later if I felt better. Her response: "Would you mind if I ate it?"
She proceeded to devour my dinner as well. The waitress comes over and says "Goodness. When is your due date?" So she says that she is due in two months. First off, I couldn't believe the waitress asked that, but then I was floored at the girl's response. Unbelievable. Being the gentleman that I am, I picked up the check because hey, it wasn't going to pay itself. I kindly said it was "nice to meet you," got in my car, and went to the bar. Well, she followed me.
She followed me to the bar, and when I got out of my car, she proceeded to berate me over why I was going out instead of going home. Now she's calling me a liar in the parking lot of the bar I frequent, and my work buddies are starting to roll in. I never heard the end of it. I said to heck with this, got in my car, and drove home.
98. I Relieved Him Of His Duty
I was married to a psycho. He said he was going to the woods to take his own life. So, I called the authorities and told them I thought he was having a PTSD episode from being in the service. They stopped him, took his piece, and informed me he was NEVER IN THE ARMED FORCES.
This was four years into my marriage. I took photos of all the holes in my walls and got myself a restraining order and a divorce. The courts don't appreciate stolen valor being your excuse for brutality and emotional manipulation. He did the same to his second wife, who also divorced him.
99. Showing Off His Creepy Side
I once browned out at a club and remember briefly meeting a guy in a suit. The next day, I woke up to a text from Willis, the guy in the suit. Turns out we both didn't really remember each other. Over text, he seemed nice enough and we both thought it'd be a funny experience if we went on a date.
We met up for lunch and upon meeting him, I didn't really have much hope for a second date. He was kind of awkward and tried a little too hard to stunt. But whatever, he seemed like a nice guy. We sat down for pizza and started getting to know each other.
I told him I was studying public policy and was delighted when he asked what kind of policy I wanted to focus on (most people don't really care). I went on a whole rant about how much I wanted to make education policy better because I thought education had the potential to dramatically change lives, especially for those not born into much.
After I finished my rant, he says, "That's cool but I don't really believe in education for low-income people because when I grow up, I want maids and butlers and, like, someone has to do that”. I responded, "Some people have that viewpoint," and started to look for ways to end the date. But the worst was yet to come.
After we finished eating, I made up an excuse to leave an hour earlier than planned. He asked if I really had to go and said, "I should just kill you and keep you with me”. Smooth. I told him he probably shouldn't joke about that. He responded, "I would bury your body right there haha”.
I hailed down a cab after that.
100. Hung Up On Her Ex
We were riding the train home from a date. I looked over, and couldn't believe my eyes.
She was logging in to her ex-boyfriend’s Facebook account. I asked her what she was doing, and she straight-up told me that she was logging in to her ex-boyfriend’s Facebook account. When I asked why, she said, “I’m just checking up on him; I want to make sure he’s OK. He never changed his password”.
Her checking up on him became reading through his statuses and his private messages. I asked why she couldn’t just look at his profile normally, and she said he blocked me. When I asked why she couldn’t just text him if it was that big of a deal, she said he blocked her number too.
I had so many more questions, but she started getting mad and defensive, and I still had a long train ride home, so I let it be.
101. Just Pop A Squat
I was in France and having a lovely dinner at a sidewalk cafe with a young lady I met the day prior. But in the middle of our dinner, she did something utterly deranged. She excused herself to use the restroom, got up, walked about ten feet, squatted, and peed in the gutter. Yup, no second date after that.
102. Bait And Switch
When she responded to a “Hi” on Tinder with something like “hey cutie, want to come to my parents’ house?” We chatted for a bit, and according to her she wasn’t looking for anything serious but she wanted me to pick her up, take her out to dinner, and maybe get it on afterwards. Very transactional, which kind of stung but whatever she was hot.
I looked up the address she gave me. When I read it, I got a small, dark feeling. I was surprised to find a neighborhood I did some work in, and that the house was one I knew was for sale. Specifically, the owner passed and it was being gutted to be resold by his kids. At this point I was 100% convinced this was a scam, but somewhat curious, I decided to drive by and see if anyone was there.
I texted her I was coming, but in a different type of car. It was a really expensive neighborhood on a sea-cliff, and it felt like an adventure. I took my work truck. I drove by and some huge dude comes out of the house, stares at my truck, and goes back in. I could see other people inside. I noped out of there super fast. Pretty convinced it was a phishing scam to mug me, or a prank. Didn’t feel like finding out.
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103. Valentine’s Lost
My mom has been a waitress for more than 25 years and has worked her fair share of Valentine's Days. She says she's sen a lot of sad stuff, but it's the worst when little old men or women come in and eat alone because their husband or wife had passed recently and they just sit there and cry. My mom will sit down with them and give them hugs.
104. A Relaxing Vacation
I met this guy. We vibed right away and started hooking up within a day or two. This guy swept me off my feet and I couldn't help but think, “Yes! FINALLY, a real man". Then, one day he said to me: “I know this house we could go stay at for the weekend if you’re interested". Sounds great, right? But then we got there and he said he forgot his key...so he proceeded to get a crowbar.
That freaked me out, so I asked him to explain exactly whose house we were at. He assured me that it was his dad’s summer house and he definitely had permission to use it. I ignored my gut instinct and decided I was probably just freaking out for nothing and overreacting. We stayed there for about four days, with no more issues.
I slept in the master bedroom, showered there, made food in the kitchen, the works. When we left, this guy said, “Look what I got". He proceeded to show me jewelry and some credit cards from the house. I was starting to truly panic now. As naïve as I was, I still thought it was his dad’s house and he was just having a rebellious moment.
And that’s when he fessed up. I realized that I’d just helped him burglarize this home. It wasn't even his dad's house; it was his mom's ex-boyfriend’s house, and let me tell you—they did NOT give him permission to be there. His stepdad even had a restraining order on him for a similar incident a few years before.
So fast forward a few weeks—I got pulled over and snatched out of my car for having been involved in this whole thing because these people had rightfully pressed charges. I ended up narrowly avoiding doing serious time.
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