Dating is hard, we've all got to accept that sooner or later—but it's not supposed to be THIS hard.
1. Change Of Plans
I went on a date after talking with someone for a couple of weeks. The conversation online was pleasant and involved the usual small talk about hobbies, interests, etc., There were no red flags, or so I thought...We arranged to meet in the city for a coffee. When I arrived and she was already there...and she looked nothing like her pictures.
I thought to myself, "Oh, well most people tend to embellish their photos. Let's see what she's like in person". That's when I messed up BIG time. We got to talking and at one point, she asked me what I'd be doing the following weekend. I love camping and exploring, so I just told her I had a camping trip with my mates.
She asked me if she could come along and I replied, "Um, no...We only just met". She then proceeded to lose her cool, throwing a tantrum as if we'd.been dating for years. "How dare you not take me along," she snapped at me. Yet, even after she caused a scene, my idiot self decided to see the date through to the end. She continued to ask me more questions about the trip, asking which campsite I'd be going to.
I gave her a rough estimate of the location and she replied, "Oh, that's nice. I'll see you there..". I thought that was a weird response and reiterated that I was not comfortable with that. She replied, "No. I'm going there no matter what you say. You won't see me coming". She then let out a maniacal laugh. That was the last straw for me. I stood up, placed my money on the table to pay for my coffee, and walked away.
2. Three’s Company
I met a girl on Craigslist. After a few messages, we set up a date at a bar downtown. I showed up and there was an unexpected surprise waiting for me at our table—she was already there with a guy friend. No biggie; I just assumed she was playing it safe. They were at a two-person table and the place was packed. They already had drinks, so I grabbed one for myself and put it on my tab.
My date and her friend proceeded to ignore me. I tried to join in on their conversation a few times but neither of them acknowledged me. Even when I directly spoke to them to get their attention, I got one-word answers with attitude. So, I finished my drink, paid my bill, and left without saying a word. Later, I get a barrage of messages from her calling me mean and awful for sticking them with their own tab.
3. Small Town Woes
I was on a dating app in a smallish town and I had already gone on a few boring dates. But eventually, I matched with this one girl who agreed to meet with me. I was thrilled, but there was something very odd about her and the conversation we had. She was eager to meet; almost too eager. I got to the Starbucks and waited inside for about twenty minutes past our agreed meet time.
The girl texted me to tell me she was running late, and she asked me to stand outside so she could see me as she drove by. I looked over and there ws another dude standing on the sidewalk with his phone in his hand. I recognized him from the gym, so I asked him if he was also meeting a girl. It turned out the girl was pulling a fast one on us both as revenge for her girlfriend who we both apparently dated.
4. The Sound Of Silence
On our date, we went to Dave and Buster's. I could tell she was uncomfortable. I tried to bring up topics for us to talk about, but I was only getting one-word answers or literally, “I don’t know,” even when I asked her questions about herself. We sat in silence for about five minutes before she finally showed signs of life.
She got up to go to the bathroom and when she came back, I just straight up said to her, “Hey, if you’re not having a good time, you’re more than welcome to leave. It’s perfectly fine". That's when things went completely south. She got insulted by what I said and picked up her purse to leave. I repeated myself and said, “If you’re having fun, I’m more than happy to stay, but like, we’re not even talking right now".
So she got up and left and I ordered another drink, waited a bit to watch the rest of the game on TV, then left. I got a text from her saying how insulted she was that I would ask her if she wanted to leave, etc. I just said, “I tried talking to you for 15 minutes and got no responses". She then explained that sometimes she just doesn’t feel like talking and I was cruel for not being okay with that.
5. A Quick End
I sat down and he immediately said, "Oh yes, you are hotter than your pictures and you're my girlfriend now". Cleary, he came on real strong. I chalked it up to keenness at first or maybe a weird sense of humor. I figured I'd at least stick around for a drink or two, just to feel it out. I even offered to buy the first round, partly as an excuse to get away from the table for a second.
I made some unrelated comment to the bartender that made him laugh, and when I got back to the table, my date caught me completely off guard. He started yelling and slamming his fists on the table, demanding that I tell him what I said to the bartender and whether I thought he was good-looking or not. He had somehow gotten jealous of this bartender five minutes after meeting me.
6. Miscommunication?
I had a crush on this guy in high school and my friend kept urging me to talk to him. I finally got the nerve to ask him out and apparently, he liked me too, or so I thought. We talked often and exchanged notes in the hallway. He even asked me to homecoming and I said yes. I was so excited; I bought a new dress and everything!
But when I got to the football game, everything changed for the worst. I saw my crush in the stands and I told him I was going to go sit with him for the game. He told me I couldn’t do that. I asked him why and he said it was because he was with—get this—his girlfriend. I was devastated and embarrassed, to say the least.
7. Why Did He Even Come Over?
I invited this guy from Tinder over to my place because he seemed pretty nice and we had a lot in common. He was decent looking on his profile, so I thought, why not? For context, I had just moved into my apartment and I didn't have a nice setup yet besides a table and a few chairs. The second he walked in, he waved the first red flag—he asked me why I didn't have any slippers for guests.
I was a bit confused but figured maybe he just lived in a fancier household than me (and yes, he made it clear he did). I said I didn't have any slippers, and he just shrugged it off. We then went to my balcony to hang out and he spent twenty minutes crying about how much he still loved and missed his ex-girlfriend. I just nodded along to be nice, but it was strange.
We eventually went back inside and he immediately started grilling me about my lack of furniture. "Where’s your TV? Couch?" When I explained that I didn't have the money at the moment to buy nice furniture, he scoffed and just kept nitpicking.
8. Maybe She’s A Werewolf
I went on a date with a girl in college, a cutie from my class who I had been trying to get a date with for a while. I picked her up to drive to dinner, and it’s worth mentioning I live in Wisconsin and it was January, so it was pretty cold outside. While I was driving, she startled me with her next move—she proceeded to undo her belt, open the door, leap out of the car into a snowbank, and run into the woods.
I had to chase her down and convince her to get back in the car with me before she lost her feet to frostbite. We didn't date anymore, but I did check in on her every once in a while.
9. Cats, Cats, Everywhere There’s Cats
I met this girl online. She seemed nice, geeky, and into a lot of the same nerd stuff that I was. She was cute in her photos too. She dodged me several times about going on an actual date, but finally, we managed to set something up. She wanted me to come to her house so she could make us dinner and watch a movie together. We were both introverts, so that was fine by me.
She said she lived in Houston, but it was actually over an hour outside of it. When I got to her 'house', my jaw dropped—it was actually a trailer in the middle of the woods on a wooded lot full of trash. Turns out, they didn't have trash service, so she basically just threw it outside. At first, I thought I was seeing cats everywhere, but it turned out to be cats mixed in with a few massive rats.
Still, I'd driven an hour plus, and I was already there, so I climbed up the decrepit deck and knocked on the door. When she opened it, the smell of cat urine poured out of the trailer and invaded my nostrils. When I got inside, there were more cats everywhere. Orange cats, brown cats, old cats, young cats. Cats everywhere.
Her mom was "cooking dinner" for us, which was frozen microwaved dinner. This girl then dragged me to her room and attacked me like an animal in heat. I told her I had to go to the restroom but it was covered in cat waste and litter. Just box after box, in the shower and everything. I couldn't do it. I went and told her I’d forgotten flowers in my car and drove away as fast as I could.
10. Oh, Those Summer Nights
A couple of years ago I went on a date with this girl who I had a crush on in my college math class. I was too scared to ask her out and didn’t do so until one summer day when she hit me up on Snapchat asking about some tea places that I knew of. I told her some places, then I shot my shot, saying we should check one out together.
She agreed. I picked her up and we went to the tea place. We had a really nice time and even played Jenga. I didn’t want the date to end, so I took her to a lighthouse on the beach. We got to know each other so well and had nothing but a great time laughing the night away. Night eventually came and she had to go home, but we planned on hanging out again soon.
A week or two later, I woke up and checked my Instagram. The first post I saw made my blood run cold. It was her with another dude at the same beach holding on to each other. Mind you, she told me she was single and not talking to anyone. I was heartbroken even though we only hung out that one time.
11. At Least She Didn’t Feel Awkward
When I was in high school, I went on a date with a friend of a friend. We went and saw a movie, then went out for dinner. I was nervous and awkward, and it ended without much fanfare. The date went OK, and there wasn't a second one, but that's not the bad part. About a month later, I went to a party at our mutual friend's house.
I saw her there and was afraid it might be a little awkward. I had no idea she was invited. About an hour into the party, she came up and started talking to the mutual friend, while I was standing nearby. After a few minutes of talking, the girl I had gone on a less-than-awesome date with came up and introduced herself to me.
12. Truth Is Subjective
I invited a girl from Tinder over to my house after a very steamy conversation (led by her). After bringing her to my place, she proceeded to absolutely ignore me and at best give me one-word answers to every line of the get-to-know-you conversation, acting like I was inconveniencing her by taking her attention away from her phone.
Any time I tried to make a move, I got shot down instantly. This went on for a few hours, so I put Netflix on. Big mistake on my part, apparently. Just as I was about to say it was time to leave, with no warning whatsoever, she straddled me and started aggressively making out with me. It was disgusting—a bunch of food residue from her mouth got into mine. She hadn’t brushed her teeth.
I noped out of that and we had a very quiet drive back to her house. Before I even left her driveway, she was texting me saying how great it went and that she wanted to see me again soon. Needless to say, that did not happen!
13. You’re As Old As You Feel
I went on a date with a guy on Bumble. We made plans for him to pick me up and go to a local restaurant for dinner. It ended up snowing the night before and the road had developed a layer of ice on top. I suggested rescheduling, but he insisted. He picked me up, and when leaving my neighborhood, he started to slide on the ice. My life flashed before my eyes and we ended up rear-ending the car at the end of my road.
Thankfully, everyone was okay. I was pretty shaken up, but we continued on with dinner and the rest of the night was pretty mild. The following Monday, his insurance ended up calling me, asking what happened. I called him to say I didn’t want to get any further involved after having spent forever on the phone with the adjustor and he responded by asking me out.
Not only that, but he ended up standing me up anyway. He claimed, “in his older age” he tends to be more forgetful…He was 27.
14. You’re Focused On The Wrong Thing
My date phoned me the morning before our date at 2 am to say she was so excited about our date. Then, mid-conversation, she crashed her car. After that, I didn’t hear from her until the date—I had to pick her up at that point because totaled her car. The date started well and I took her to a fancy sushi place, but she did not eat one piece as she was talking the entire time.
I slowly established that she had not slept for a few days and her eyes were rolling. I settled the bill and took her home to a very judgmental roommate. As I was walking back to my car, I heard a bloodcurdling shriek..."Where is my goodnight kiss?!" My anxiety kicked in and I started running to my car. I looked back and she was chasing me, still screaming.
Neighbors from all over her complex started watching from their homes but I somehow managed to escape. Months later, I ran into her roommate out on the town and she said, "Oh yes, you were the one who ate all the sushi".
15. It’s Too Much
I met this guy Ron on OkCupid. He seemed nice enough, even though he was older than his profile said. We chatted over the phone a few times and he came across okay enough to meet. So, we did. I went to his house for the first meeting because I was honest in telling him what wouldn't be happening. I figured he was gentleman enough to respect my wishes.
We chatted for a while on his back porch and watched a movie in his living room. But then he started to act weird around me—he would touch me and I reminded him that wasn't happening and to please stop. "You're just so beautiful, I can't help myself". He could help himself. I was suddenly "very tired" and wanted to head home. He started texting me, just constantly bombarding me with compliments and it was smothering.
I talked about boundaries with him, but he just ignored me. He even offered me a key to his house. so I could pop over anytime. He wanted to get a dog so I could come over and walk it while he was at work. He also mentioned a work trip to Hawaii several months in advance and told me he wanted to take me. I started to pull away from him a little and explained that he was being too much too fast.
After a long break, we decided to meet up again because I make bad choices sometimes, admittedly. Things just got worse from that point on. He started touching me again, smothering me. He legitimately would not leave his hands to himself, so I leaned forward on my knees so he couldn't touch me. I told him I was leaving and he walked me back to my truck because it was late and dark.
He hugged me and wouldn't let go. I tried pulling back and telling him to let go, panicking, but he wouldn't. I started to nervously laugh because I was in full panic mode. I opened my door and he stood beside it, not letting me close it. I couldn't drive my car forward because I was in a parking garage and there was a car in front of me. If I go reversed, my door would have probably gotten torn off.
When I went ballistic and screamed at him to move, he backed up, made a snarky remark, and I finally went home. He started texting me again—long, long paragraphs about how when I "hugged him" he felt sparks he'd never felt before, how I mean so much to him, and how he's never felt this connected. I just stopped responding.
He started texting me more, I don't answer. Then he got mean, but I still didn't answer. I headed to work the next Monday and showed the text messages and his face to security and told them to not let him on campus. Security couldn't believe the text messages. I learned my lesson BIG TIME with him.
16. What Did I Say?
I met a girl through a friend at a party and we went on a few dates. On one of them, we ended up at a hotel and decided to stay the whole weekend. The last night, after a few drinks, we were chatting under the sheets. Drinks, snacks, good times. Suddenly, she switched to a whole other conversation. Not a simple switching of subjects, either.
This was a quick and smooth transition from a real conversation to one that was between her and…someone else. I was confused, but I brushed it off. This happened a couple of times. The third time though, I had to say something; I couldn’t just let it go. It was horrifying—she was weirded out and was just as confused as I was when I listened to the things she said.
I told her it was like she had parallel conversations going on in her head. She became visibly frightened by herself and nervously panicked, ultimately breaking down and thinking she was crazy. I tried to comfort her until we fell asleep. I found out later she was diagnosed bipolar, but never really heard from her after that night.
17. Strongly Opinionated
I went on a date with a girl who suggested a restaurant but it was closed when we got there. She told me it was where she'd had her wedding reception after marrying her much older husband. Then, at the next restaurant, she revealed her true colors—immediately asked me how I felt about Trump while telling me how great she thought he was before I answered.,
Then she drank most of the bottle of vino we ordered, made rude comments in the restaurant out loud, and told me constantly that she made more than I did (I'm not sure if she was right, but it was a weird thing to care about regardless). She told me she forgot my name twice and spent the entire car ride back to her place trying to convince me Obama's birth certificate was a forgery.
18. Older, Not Wiser
I was 18 with a Plenty of Fish profile and I got catfished by this dude who was about 20 years older than me. We met at Starbucks and upon seeing him, I knew I was out of my depth, but I didn't know what to do so I went along with the date. Worst decision ever. He would ask me my interests and then shoot them down. For example, he'd be like: “You're into Harry Potter? I think that is so childish!”
I knew I needed to nope out of there, but he kept insisting I come over to his place. He used the fact he bought me a coffee to make me feel guilty. I agreed to go to a park but that was the most he was going to get. I said I had to drive separately as I had to go somewhere later and during the drive, I called a friend and asked her to call me in fifteen minutes to give me an excuse to bail.
At the park, he mentioned that he knew he was older and attributed that to my "strange" behavior. He found it so odd that I did not want to see his house—he explained that he only invited me because he felt a connection and knew I wouldn't want to meet him if I knew he wasn't like his picture anymore. Not long after my bailout call came, he became so cold and it was scary.
Thankfully, I slipped off after a very awkward hug.
19. The Divine Plan
I went on a first date with a guy after meeting him on a dating site. The phone calls went well so I thought, why not. We met at the mall. Right off the bat, I got a weird vibe. He proceeded to tell me how many kids we would have, and how he would physically punish them whenever they were disobedient. The guy was fully serious, too—he said we had to do it because "it’s what God wants".
He ended up following me to my car and I was thankful it was daytime in a busy mall with a security guard watching. He then tried to make out me, but I slapped him and drove away.
20. The Wrong Film
The guy was hot and interesting, so I invited him over thinking we’d have some casual fun. He arrived and it was going fine—we had loads in common including film taste. We decided to watch a movie and settled on Nymphomaniac, which neither of us had seen or known much about. Little did we know what we were getting ourselves into.
It was a very disturbing film for various reasons, awkward and painful viewing. It totally ruined the mood. We finished the movie and mutually decided to end the date. I didn’t bother to arrange another date.
21. Oldest Trick In The Book
I got to the restaurant first and waited outside. When he arrived, he was extremely energetic past the point of being normal. When we sat down, I could see his eyes were dilated and unblinking. I assumed by that point he had done some sort of substance before the date. We agreed to have one drink at the restaurant, then go somewhere else for food.
During the drink portion of the date, he told me he could get me a good job selling cars at his business and then asked me to move in with him to annoy his ex-wife. I just chuckled and brushed it off. I told him I'd meet him at the restaurant and he shocked me with his next move—he followed me to my car, got in on the passenger side, and wanted me to drive him there.
I was a little freaked out but I tried to roll with it. We got to the restaurant and the vibes were all off at that point. I was significantly freaked out, so I used the bathroom excuse to ditch him and leave. I got to the front and realized I left my purse behind, so I asked the hostess for help. I told her to please find a way to get me out of the date. Fast forward about ten minutes and a glass of pinot later.
The manager came in making his rounds to the tables, stopped at ours, and asked for my name. He said I had a phone call up at the front. Not the smoothest line, but I went with it. I told my date I'd be right back, then grabbed my purse and hightailed it out of there.
22. It’s Shark Week Every Week
She had a weird obsession with sharks. She had shark decals on her car, shark tattoos, and wouldn't talk about anything but sharks. After lunch, she revealed she had no money, so I had to pay. I was going to anyway, but for her to bring no money on a date and just presume I would pay was pretty insulting.
23. Multi-Level Madness
We met up at a café. Within the first minute, he pulled out a bunch of brochures and started telling me how amazing Amway and its products are. He told me all about how you could gain access to all kinds of cool events and stuff by becoming a sales rep, etc. I was pretty annoyed that I was scammed into an MLM pitch meeting and I told him so.
After I said that, he completely lost it. He got extremely angry and defensive. He said: "I'm not trying to recruit you! I knew you were from Michigan and Amway was founded there, so I thought it'd be a good topic!" Right. I told him I was leaving and asked the waiter for the check. The dude literally then screamed: "SEPARATE CHECKS!" at the waiter, drawing the attention of everyone in the cafe.
I started getting a bit freaked out and was scared to walk to my car because the dude was literally shaking with rage. I was terrified he'd try to follow me, so when we went outside, I remained standing by the café door thinking he would walk ahead to his car first. Nope. Instead, he took it as an opportunity to stand there and scream at me in the parking lot.
H was still insisting he wasn't trying to recruit me and said I ruined the date by accusing him. As if somehow him yelling at me in a parking lot is going to change my mind. Finally, I couldn't take anymore—I just went to my car, locked the doors quickly, and drove multiple circles before going home.
24. If The Shoe Fits…
I was taking part in a college "Cinderella" activity where girls put one of their shoes in a pile. A guy would pick a shoe and he'd go out on a date with the girl who the shoe belonged to. My roommates and I all did it as a group and it was supposed to be fun...until the weirdest guy picked my shoe. I honored the activity and went on the date, which was at a bowling alley.
Every time I got up to bowl, he would shout at the top of his lungs like: "THAT'S MY DATE!" He also shot put the bowling ball and probably ruined the lane. Sometimes his throws were so bad they would go down someone else's lane. At one point, he tried to kiss me in front of everyone...It was terrible.
25. Just Make A Decision
I matched with a girl on Bumble and we talked over the course of a few weeks. We made plans to meet u one weekend. I texted her the day before to see if we were still on. She didn't reply until the day of. She said that she actually had somewhere to be later in the day, but asked me if I wanted to get coffee before then.
She also asked me if I could pick her up because her car was in the shop. I said yes to both, like a true idiot. She asked me if I knew of any places we could go. I said there was a Starbucks in my area, but she asked me if I knew of any places other than Starbucks. I went on Google, found a neat little local coffee place, and threw that one by her.
She didn't respond for 45 minutes. I ended up shooting her another text asking her how that sounded. She replied back that it sounded good, but the place was closing within the next twenty minutes. I went back to Google and found a different coffee place in her area that didn't close for another two hours. I threw that one by her and then she texted back asking if we could take a raincheck.
I said, "Sure," but didn't have much intention of reaching out to her again. She had already flaked twice before and the fact that she basically ended up wasting most of my afternoon kind of dampened my interest a bit.
26. We’re All Confused
It was our third date and we decided to go to a club. It was getting pretty late so we ordered a Lyft to beat the crowds of people trying to exit at the same time. We exited the club and someone pulled my arm hard when we got outside. I turned around and my face went white—a random guy was accusing me of ghosting him and leaving him at a club with the bill.
I told him he had me confused with someone else which only made him more and more upset. He kept reaching and pulling at my arms. My date pushed the random guy away and pulled me closer, which only set him off even more. Security noticed and thought we were causing an issue with the dude. My date tried explaining what was going on and the random dude lunged at me.
I remember I had my taser with me, so I took it out and laid it on him. He fell to the ground, confused. I'm pretty sure he mistook me for someone else, but that was terrifying.
27. Third Wheel
I had been talking to a woman for a couple of weeks and she ran hot and cold. Mostly cold. I was thinking about moving on from her, but then one lonely Saturday night, she called and invited me to a bar for a few drinks. I told myself, why not, and went. when I got there, she was with one of her girlfriends. Her friend was a late 20-something and chatty as anything.
Immediately, I could tell my date was far more interested in her friend’s welfare than in me. It later came out that the friend’s husband was a jealous weirdo. I played along, had a few drinks, and listened to the friend vent her problems, but it was clear I was not part of the night’s festivities. Whatever. It was better than being home alone on a Saturday night. Then, an hour or so later, things got interesting—the weirdo husband showed up.
He charged up to our table, whipped out a camera, and took a picture of all of us. He muttered some vague threat to his wife before leaving. The friend got super upset and decided to go home. My date wanted to walk her out and we went outside to say goodbyes. She walked away and I turned around, thinking finally I got my date to myself.
Then I see she'd already hopped inside her car. She drove off without even a wave goodbye, leaving me all alone. I went back into the bar had a couple more drinks hoping to meet someone, but I suck at bars. I went home an hour later.
28. Too Much, Too Soon
I met a guy online about 20 years ago. He was really smart and funny, so I gave him my number. I really enjoyed talking with him. I’m 5’7” and he said he was the same height. I was in my early 20s and he said he was in his early 30s. We decided to meet up on a Saturday morning and go to the flea market which was huge in our area at the time.
When we finally met up, I shook my head in disappointment—he was only 5’4” and in his early 40s, easy. I was mad that he had lied to me, but I really liked him and decided to continue with the date. It was my first time meeting this guy face to face, and he was all over me. Kissing me, hugging me, holding my hand, and I had a difficult time walking around because he was literally attached to my side.
It was just way too much. After the market, he wanted me to come up to his hotel room. When I said no, he was hurt and disappointed. I’m grateful that he didn’t get angry and abusive, but at the time, I couldn’t get away from him fast enough. He quickly moved on.
29. Entertain Me
I showed up for a coffee date and about five minutes in, I knew it wasn't going to be a fit. But I figured hey, might as well be polite. After about fifteen minutes of trying to make conversation and getting back one-word responses, I paused. I told her that part of my job was to talk with all sorts of people and that I was struggling to keep the conversation going with her. I then asked if she was okay.
I was legitimately concerned for her because her behavior was so abnormal, and plus, the anecdotal evidence is that I'm a fun and easy date. Her response was chilling: "Oh it's just funny watching you struggle". I stared at her for a few seconds, then told her she was a terrible person and left. I still shake my head at that one.
30. A Journey
I started chatting with this girl on Tinder. She was cute and we got on really well. I asked her out for a drink and she said sure. As I was getting ready, she texted to say she was running a bit late. Fair enough—I figured I'd go on time, grab us a table at the bar, and have a cheeky pint to calm my nerves. When I got there, she asked if I could just meet her halfway.
Since it was getting dark, I agreed to meet with her. I was walking and walking but there was no sign of her. She kept texting me updates, telling me which roads to turn on and whatnot, but I was starting to feel a little uncomfortable with it all. Eventually, I came to a house. I hesitantly knocked on the door and some chick in nearly see-through leggings and a matching black top opened the door.
She looked nothing at all like her profile and I felt I'd been catfished. She welcomed me in saying she'd just be a few more minutes and we can go. Me being me, I decided to be polite and play along to the end of the night knowing full well I was never going to talk to her again. We went inside where she then had a screaming competition with her mom and stormed off to her room.
I awkwardly followed, and when I entered her room, I discovered her secret—she was a massive hoarder. Her room was a mess. In the middle of her bed, there was a half-eaten kebab. She invited me to join her and I awkwardly sat on the edge of the bed while she ate it. After chatting for a bit, I mentioned going back out for that drink but she said she wanted to stay in.
When it started to get late, she tried to make several moves on me but I politely turned her down. I excused myself to go to the loo, noped it out the house, and went home. When she realized I'd gone, she texted me a bombardment of nasty messages and threatened to come round mine with a bunch of her mates and hurt me.
I ignored it until she texted me my own address (which I'd never told her) and said she'd see me in a few. Thankfully she never turned up!
31. On Thin Ice
I went on what was supposed to be a simple coffee date, but our shopping center was hosting an ice rink that she absolutely wanted to go to. I have poor stability even on solid ground, but I thought maybe a bit of messing around on an ice rink would make her laugh. Nope. Within seconds, I slipped and outright twisted my ankle and wrist.
I needed help being carried out to sit on a bench and try to recover. But here's the kicker—she couldn't care less and continued skating by herself, attracting the attention of another skater. I watched the two of them leave without her even looking back to check on me.
32. Dinner And A Show
There was a girl in my IT support training session and she knew so little about computers I was positive she walked into the wrong class and just stuck around. I figured maybe she just wasn’t used to working in an enterprise-level company and maybe she was just out of her element. Either way, I didn’t think she was sticking around so I asked her out.
I later found out that she was an aspiring actress and not a computer professional at all; she just wanted to see if she could play one. The date wasn’t so bad but shortly after the food arrived, her behavior became startlingly weird—started playing with her food. I mean, full-on making sounds while playing with it. I noticed, then made a comment like, “Don’t play with your food,” as a joke.
But she just glared at me then went back to playing with her food. I think I gave her the benefit of the doubt for long enough at that point. She was really attractive which was why I probably looked past everything...but when she started singing to her steak, I kind of just gave up.
33. Fate Can Be Funny
I finally went on a date with a guy from work who had asked me out about 20 times. It was as awful as expected. He would sit silently staring at my chest then suddenly blurt out some ‘fun fact’ before going back to boob-watching. So, I went to the loo and climbed out the window; except, the worst-case scenario happened—I got stuck. So stuck that the restaurant had to phone for the fire brigade to get me out.
My date had come into the bathroom to watch, but all he did was keep staring at my bum, trying to touch it. The firemen threw him out so he went round the back of the pub (where my top half was sticking out) and tried kissing me there. As my arms were through the hole, I managed to land a right hook on his face.
The firemen made him leave. When I saw him at work the next day, he had a massive black eye and told everyone I had freaked out and attacked him! About three years later, I met my now-husband. One date night, whilst out with friends, my husband was asked about funny moments at his job. Coincidentally, he is a fireman. He told the story of a woman who was trapped in a bathroom window trying to escape a date!
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34. Ah, Young Love
One time in the eighth grade, I finally got the courage to ask this girl out. She just so happened to be the friend of my best friend’s current girlfriend, so we decided to make it a double date. During the movie, everything was going as planned. I sat by her while my friend sat with his girlfriend. Then we saw a couple of her girlfriends walk into the theater.
They happened to see the girl I was with right away. She then motioned with her hand for her friends to come over there. When her friends got to where we were sitting, the girl I asked out turned to me and asked, "Can you scoot down a seat so I can sit next to my friends?" I said sure, so I got up, and just walked out of the theater.
35. No One Had Fun That Day
The girl was totally normal, nice, and well-mannered. It was the circumstances that made it awful. We decided to meet at this bar/grill with a big outdoor patio in the late afternoon one weekend. We got there and the place was PACKED, so the hostess sat us at a small table for two. As soon as we sat, we heard an older woman say my date’s name in kind of a shocked tone.
My date turned her head and her face dropped. It was her MOM! Her mother just happened to be there getting some drinks with friends, so we had to spend our whole first date making chit-chat and sipping our drinks with her mother about five feet away.
36. Red Hot Love
I once invited a girl I liked a lot to see a movie and she agreed. We chatted about this and that before the movie started and out of the blue, she mentioned her boyfriend. I kept talking as if it was no issue, but halfway through the movie, I excused myself to the bathroom. I walked out and planned to never see her again.
She called me about a week later saying had lied about the boyfriend because she was nervous. I liked her so much that I decided I would give her another chance. On the second date, it didn't get any better. She told me she was a volunteer firefighter which was cool. But the only thing she was interested in was... fire. "Have you ever seen a house burn? It's so beautiful!"
Fire this, fire that on and on through the evening. Every time I tried to draw the topic away from fires, she found a way to come back to it. Needless to say, I never called her again!
37. Did It Hurt When You Fell… From Bed?
We were getting it on and he launched me out of bed. My head broke the fall. I kept blacking out so he took me to the ER. As I was sitting in bed with a neck brace on, awaiting tests, he asked if he could see me again. I just stared at him. Twelve hours later, I was released with a severe concussion. The doctor asked me to take a month off of work.
I couldn’t do that so she lowered it to a week if I agreed to sleep during most of it. So, for seven days, I was on medication that knocked me completely out. I would wake up long enough to eat, drink some water, pee, and take more medication. The adult cuddling wasn’t even that good… and no, I never saw him again.
38. An Unsettling Turn Of Events
I met a girl online who was beautiful, fit, and smart, but a little older; only by about five years. She was a dentist and we had an awesome date. She came over and we did the deed—she scratched up my back and all, but whatever, it was great. That morning, I woke up to the sound of plates breaking. I ran downstairs and saw her throwing out all my plates into the trashcan.
I calmly asked her why she was doing that and she said I deserved better plates. OK, I suppose so. Then she asked to go upstairs and cuddle. That's when things got scary. She started whispering to me about how she lost her ability to practice dentistry and that she was not what she seemed. I laughed a little and started to get nervous. When I asked her if she was OK, She ran off to my bathroom and locked the door.
At that point, I was pretty terrified she was going to either use my razor on herself or on me. I heard the sound of canisters being emptied out and nervously asked what she was doing. She came out and says she made a mistake. She was married and has a child but she was not allowed to see her kid or stay at the house. At that point, I realized I was dealing with someone ill.
I told her to come downstairs and I'd cook her some eggs. I had no plates anymore, so I offered to take her out for a quick sandwich. We headed over to the place and not a single word was exchanged. I picked up both sandwiches and we ate them on a bench outside. She said thank you and called me cute, then left me there. She just walked away without a word and I didn’t hear from her again.
39. The Art Of Pitching Woo
I was 10 years old and had a huge crush on my best guy friend who probably still thought girls had cooties. Being a hopeless romantic, I decided what better date to go on than dinner and a movie. My mother, as our chaperone, brought us to Olive Garden where I excused myself to the bathroom and proceeded to change into the only dress I owned.
Then we went out to the movies where I insisted that my mother and sister sit in a different row from us and, faking the damsel in distress, asked him if he would hold my hand if I got scared. Even better, when we dropped him off at home that night, to his horror, I kissed him on the cheek in front of his mom and older sister.
I then spent the next few YEARS being ridiculed about the whole event while his sister told the story to all our friends every chance she got. Needless to say, I embarrassed myself pretty well, and probably scarred this poor boy for most of his prepubescent life.
40. Jokes On Him
I showed up at the pub and he looked only vaguely like his pictures. I thought well, I'm not really attracted to him, but maybe he has a good personality. As we went deeper into the date, I got my answer. He started asking me questions about my interests and then dissecting and belittling my answers. The one that I remember the most was, "What kind of movies do you like?"
I replied that I like comedies, to which he responded, "Oh, I only like documentaries because I actually can learn something. I surround myself with friends who are funny so that's where I get my humor". After several interactions like that, I just went home. I was surprised when he texted me asking if I wanted to hang out again. He does know how to be funny after all.
41. A Whirlwind Romance
I excitedly met up with this girl at a bar and the first thing she told me is that my hair is gross. I take very good care of my hair; she just doesn’t like long hair on dudes. We got the pleasantries out of the way and then she went on to brag about how she'd been with several guys who were over six feet (I’m 5’8"). She then asked me to send her $30 because “These nails didn’t do themselves".
But that's not even the worst part. Continuing on, she started roasting me for living with my family even though she also lived with her family. At the end of the date, she asked me to sit in her car with her. I agreed and we talked for a bit. It got a bit too political, which I didn't like, but it was better than hearing about her escapades. After a while, she told me that she was leaving because some other guy had just arrived to pick her up.
42. Three’s A Crowd
I once went with a larger group of friends to an outdoor movie festival that was happening in a remote place. You could only get there by boat, but it still attracted quite a number of people. The options were camping or a super expensive hotel. I was in college, so we camped. The place also had an outside bar and restaurant.
I was sharing my tent with my then-girlfriend and one of my exes had tagged along because we were on good terms and she was part of my group of friends. Fast forward to the first evening of the festival and we were grabbing dinner at the venue. I bumped into another of my exes. Being the polite person that I am, I said hi and asked her how she was doing.
She later sat down at the same table. Things were beginning to get awkward for me at that point. As I was finishing my food, guess what? Another ex showed up with her current boyfriend and sat down at the table. Mind you, at that moment, there was my current girlfriend and three of my exes sitting at the same table, along with some other people.
One of my friends decided to make things extra weird by very loudly pointing out the situation and ensuring everyone there knew who everyone else was. Needless to say, I had a freshly minted ex by the time the night was over.
43. Mistake Number One
I talked to this guy on OkCupid for about three or four days. I learned an important lesson after I made the mistake of telling him where I work. One night, he told me that he was going to the casino with his friends. In the morning, he said that he won some money and used it to buy me a gift because he really felt that this was going to be something special.
I told him I was uncomfortable with him buying me a gift as we had only been chatting with each other for a few days. But he didn't want to hear it—he replied that he was going to take the next bus and get off at the stop near my work. He told me to meet him there if I wanted the gift and if I felt the same way. I didn’t respond.
I also didn’t show up. When I left work for the day hours later, I saw him sitting at the bus stop with a brown paper bag in his hands. I blocked him and changed jobs. It was just a fast-food part-time thing during college, so I was easily able to find something else. I didn’t feel safe working there anymore.
44. Memory Of A Goldfish
I’d been messaging a girl on Tinder for a couple of weeks. We even spoke on the phone some nights and she seemed pretty cool. We organized a date to check out a food market in the city and I offered to pick her up from her place. I let her know when I was on my way, but when I got there and let her know I was outside, there was no answer.
She lived in a gated apartment block so all I could really do was call and text. I must have waited out there for about 20 minutes trying to let her know I had arrived, but still no response. I went to grab myself a burrito near her place and she called me later with an update that made my blood boil—she told me she’d "forgotten about our date"… even though I literally called her like 30 minutes beforehand to confirm.
Anyway, she begged me to come back, and stupidly I obliged. By the time we went out, most places to eat were closed and she didn’t want to go to any bars or anything. She barely made an effort to engage in conversation and was just scrolling on her phone while we drove around. In the end, we decided to just call it a night.
45. A Sly Twist Of Fate
This was the first woman I went on a date with after getting out of the army. She pretended to twist her ankle in the restroom as the bill came out. She then had me carry her, fireman style, outside to her car where she tried to convince me she couldn't drive because it put pressure on her foot (she was trying to get me to invite her back to my place, I assume).
When I asked her if any family members could pick her up, she said no. I was standing outside the driver's door at the time and she asked if I could just look inside to see if her foot looked normal. My naïve self just leaned in and that was a big mistake–she tried to kiss me. I pulled back saying I wasn't feeling that kind of connection.
She called me a terrible person, then burned out of the parking lot. She later proceeded to blow up my phone saying how sorry she was and that we were soulmates.
46. He Tried So Hard And Yet…
I convinced a girl who I was crazy about to go out on a date with me. I knew I had to make it count. We lived by the ocean and she had dropped the hint that she had never been out on the pier at our local beach. Challenge accepted. I nervously drove her down to the beach and we proceeded to slowly walk out on the pier together.
She seemed hesitant from the beginning. We stopped short of the end and I leaned against the railing over the water while she stood back a bit from the edge. She didn’t really seem into it at all. Awkwardly I said, “This is a great view, huh?” Just then, two pigeons flew up and landed at our feet. “Sweet, chicks dig birds,” I thought to myself.
To my horror, the birds began to make passionate pigeon love in front of us while neither of us spoke. I had never witnessed such athletic passion. I quickly scanned around and saw a couple holding roses on the other side of the pier. “Awesome, they look romantic, chicks dig romance,” I thought to myself. We quickly walked away stood next to the happy couple.
The man and woman were holding each other and both holding roses but something seemed off. I glanced up and noticed that both were sobbing, the girl I was with noticed too. As we were both looking, the couple took their roses and cast them into the sea. I had posted us up next to a funeral, some kind of sea burial.
Welp, I had executed one of the worst dates of all time. Just as I had accepted my failure, my date started getting fidgety. Based on her body language and her expression it dawned that she hadn't told me about the pier as a hint but because she was terrified of it. Turns out she had a fear of heights and the ocean.
47. It Could Have Gone Better
I met this girl on the Internet and she seemed really nice and down-to-earth. We had a lot in common including our hobbies and politics and stuff like that, so I thought we might hit it off. We agreed to meet up in person at a coffee place. Now, bear in mind that I'm not super attractive and up to this point, she hadn't seen any pictures of me.
Instead, we had pre-arranged recognition signals. She walked in the door and I spotted her by her clothing instantly, so started waving. She got this sort of uncertain look on her face, then walked over and said, "Sam?" and when I say yes, she just said, "Haha...NO".
48. 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.
49. #BadDate
My date got mad at me for wanting to leave when all she did the entire time was mess around on her phone and post selfies of her and the coffee I bought her. I checked her Instagram profile later on (she wanted me to follow and like her photos) and the caption was disturbing. It was something like, "Treated myself #blessed #sogood #coffee". And yet, she couldn't hold a conversation at all.
50. A Whole Mess
When we went back to my house after a bike trip, she fell and broke her cervical spine. I had to take her to the ER I work at—she got admitted and put into a halo in the ICU. I met her family there. We dated for something like nine months after that, but then she totally ghosted me. Months later, out of the blue, I got served by a sheriff—she was suing me for a million dollars over her injury.
It went on and on and even to trial. It came out she had lied to me and was still married when she went on date with me. Worse yet, she ghosted me because she was also cheating on me with another guy and she was pregnant with him at the time. He even testified about her disability at the trial.
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