We’ve all had our fair share of cringe-worthy first dates. Let’s face it, it’s rare to be blessed with a classic meet-cute movie romance. But reading these comical and disastrous stories might make you feel just a bit better about your last lousy date...
1. Crossed Wires
I was on a first date with a girl I had met when I was doing community theatre. We'd gone to the movies to see Cloudy With A Chance Of Meatballs. Before the movie, we got chatting and slowly realized that it wasn't meant to be. We had too many conflicting interests and opinions, which was especially obvious when we started lightly arguing over politics and religion.
Before the movie started, I texted another friend of mine to tell her how terribly the date was going. And then I heard that fateful sound. Immediately after clicking "send" on my phone, my date's phone chimed. She pulled it out of her purse and read whatever text had come in.
She then slowly turned to me and asked, "Did you mean to send that to me?" I immediately realized and explained that I had just opened up whatever the most recent message in my inbox was and replied to that, with the intention of texting my friend. Or perhaps I'd clicked the wrong name in my contacts list (they both were the only names beginning with M in my phone.)
Needless to say, she was pretty upset. I explained that, despite our differences, I really enjoyed her company—she was brilliant and beautiful. Certainly out of my league! So, we continued the date as friends which was more awkward than we had anticipated. After the movie, we went our separate ways.
When I got back to my apartment, I texted that same friend again about how that date was incredibly uncomfortable and I doubted that there would be a follow-up. My phone chimes. "You sent it to me again".
2. Go Your Own Way
I was really into this girl and we had some real chemistry going on, until she started in on her obsession with Fleetwood Mac. At first, I didn’t realize it was a genuine obsession until I confessed that I simultaneously wasn't really a big fan of them, but didn’t mind their music. She went nuts.
It’s like that one comment flipped a switch. In front of six other people, she started cussing and telling me to apologize to her or get the heck out of her house. So, I left.
About two weeks later, a mutual friend asked why I stopped talking to her. Apparently, she thought I was going to come back later that day to apologize and make up...
3. A Perfect Storm
We met in biology class in college and we’d been to lunch a few times, but this was our first real romantic date. She was gorgeous and smart and had a smile that could melt diamonds. I was in a group project with her and took her to lunch where she confessed she had a crush on me.
We kissed before going back to class and made plans for a date that night. We had a wonderful time. Until about the time she asked me what my “deal-breaker” for dating was. In other words, what trait would someone have that would immediately make me break it off.
I said something like I wouldn’t date a puppy-kicker or other sort of terrible, mean person. For her turn, she said that she could date all kinds of guys—any physique, any race, any career, it didn’t matter. However, the one kind of guy that she absolutely, positively, would never, ever be with…was a guy with a hairy back.
I’m Iranian. You can guess how well that date ended...
4. A Blessing In Disguise
It was my first date ever (I was about 18 or 19) and we had spent about two hours talking the day before the date. We really hit it off—but our actual date was weird.
It turns out, I had more in common with the chaperone she brought to the ice cream shop than her. I get it: she brought a chaperone to make sure I wasn’t a creep. Totally understandable!
But when you make it clear that the chaperone is your youth pastor and you speak so little that the pastor felt bad enough to break the silence and talk to me, don’t expect me to want a second date!
When my date did speak, she was fully into church stuff and asked me if I wanted to come to church with her after our date... And then she kept asking, and asking, and asking...
In hindsight, I think she wanted to get me to join the church more than she wanted to date me, because I saw her in a church group later in the year rather aggressively throwing pamphlets into people's hands and a female friend of mine had a similar experience with a guy from the group, who brought along the same youth pastor...
5. Eyes On The Prize
When I first met him, he kept standing way too close to me and his breath smelled like smoke. Throughout our date, he would start looking around like he was clearly listening to surrounding conversations while I was speaking. The moment he would stop blabbing, his gaze would turn everywhere, toward anything but me. Oh, but it gets worse.
At one point he sneezed into his bare hand, looked at it and said “yeuch!” and then wiped it on his pants. An hour or so into this date, he interrupts me mid-sentence (a sentence that he was paying zero attention to) and says, in what sounded like an attempt at a sexy voice, “Hey… Wanna get out of here?”
Seeing it was the late hour of…9 pm, I said, “Well it’s getting late, I should get home…” I was grateful when I didn’t hear from him for week, before he texted me asking to hang out again while I was at an event and couldn’t really respond right away.
At my slow response time, he gave a snarky follow-up an hour later. Hilarious, considering our past conversation history...Needless to say, it didn’t work out.
6. Easy Going
We had a couple of hours to wait for dinner, so I asked if she wanted to get drinks at the bar and talk, or if she wanted to window shop and enjoy the Christmas lights because we were located in a heavily decorated part of the city. "I don't care, whatever you want to do".
After we sat and looked at the menu, she quickly put hers down. I assumed she knew what she wanted already and inquired what she had decided on. "I don't know, I'll probably just order whatever you're getting". She wouldn't make a single decision.
Eventually, I asked what she did for fun. A classic first-date question. "I shop sometimes, that's it". It was absolutely impossible to start a conversation with her. And I’m sure you could have guessed that she asked me not a single question the entire four hours we were on our date.
7. The Daily Grind
He arrived 40 minutes late with no text to say he would be running behind. But that wasn't the worst part. To add insult to injury, he turned up with his laptop and said he needed to do some work.
He gave me some cash to get him a coffee and something I wanted. While I stood in the queue, I watched him put on his headphones and open his laptop. I returned with the drinks and he said he just needed to finish this one thing, but proceeded to take a call.
I sat there for another 40 minutes with zero conversation, while he typed and chatted away on the call. This was a Saturday by the way, and he is the one who scheduled the date. After he finished, he offered for us to go to a bar and get a proper drink.
For some reason, I agreed and while we were finally chatting, he turned out to be a total schmuck. He ordered the drinks and then started having a go at me for not offering to pay, while ranting about double standards.
To be honest, I happily would have paid under normal circumstances, but I was still completely put off about waiting for 90 minutes for our date to properly commence. So, sue me for not being in the mood to pay!
8. Getting Down To Business
When we got to the good old "What you do for a living" question, my date straight-up tried to sell me on her pyramid scheme that she hadn’t once alluded to in our previous conversations.
When I politely noted I wasn't interested but would be happy to go back to our previous topic, she got argumentative in a salesperson-losing-a-client sort of way. When it was clear the mood was ruined, I stood up, paid for our drinks at the counter, and got the heck out of there!
Hilariously, some of my friends were coincidentally sitting at the table behind us (well, behind her—I could see them). They looked up from their table and gave her weird looks as she was ranting about the "life-changing opportunity" she was attempting to sell to me.
If I wasn’t already convinced this date was a failure, their looks definitely solidified my thoughts.
9. Unexpected Guests
Many years ago, I agreed to meet a lady in a coffee shop for a date. When I saw her arrive, my jaw dropped. She turned up with four screaming kids in tow, who proceeded to climb all over the chairs and just about wreck the entire place.
I was especially mind-boggled because her dating profile mentioned nothing of it. I actually had to go back to the profile and double-check that it was the right person... Needless to say, I paid for our coffees and took my leave as soon as I could.
10. Back To The Drawing Board...
The dude and I had texted and bonded over the fact that we both liked drawing, and decided a fun way to get to know each other on our first date would be to bring our sketchbooks and share what kinds of things we draw. I brought along my little Moleskine sketchbook. He brought an accordion file filled with one-page comics.
He then proceeded to read every single comic out loud to me, with character voices. There were dozens of comics. His enthusiasm was fine. The problem was the fact that he never even asked me to share my art with him, and instead made sure I was his audience the entire evening, instead of an active participant in the conversation.
Later in the date, while we were taking a walk, he pointed out a park bench and told me a story of him and his ex-girlfriend aggressively making out on it in the middle of the day, while surrounded by picnicking families. That’s far too many red flags for me...
11. Ready To Mingle
To start, he was nearly 30 minutes late to the restaurant and blamed “traffic” even though we don’t live in a city. When he turned up, he was a little tipsy, but I can understand he might have had a drink to calm his nerves. However, when I ordered a meal, he ordered three beers for himself.
After he downed a few, he really showed his true colors. He proceeded to tell me I was a seven out of 10, and to get to a 10, I should get plastic surgery because I have the potential to be a model. I told him repeatedly that I was happy with the way I looked, but he kept going on about what work I should get done.
After I’d finished eating, I said I’m going to pay for my meal then head home, but he wanted to go to a bar and convinced me to go with him. I ordered a drink then turned around to see him leaning over a couple of young ladies, who looked pretty uncomfortable. And I took that as my signal to put down my drink and leave.
One week later, I get a call from an unknown number and it’s his mother. She tells me about how he came to visit her and told her all about me. She proceeded to explain how happy she is that her boy has finally found someone and then invited me to dinner, which I turn down.
After the whole experience, the only thing I felt was sympathy for his mother...
12. Hold The Phone
I met with her for drinks. Following a greeting and hug, her head turned down to her phone. I asked if she wanted to grab something from the bar, and didn't lift her head when she told me what she wanted, nor did she come to the bar with me. Okay. Whatever.
Fortunately, I was in a very open and chill state of mind at the time and wanted to gain experience and roll with the punches. The other 40% of the time when she wasn’t on her phone, she was talking about herself. This was more bearable—not great, but bearable.
That's part of the idea of a date anyway, get to know the other person. But most of that was about her awful ex and how terrible their breakup was. Sadly, there was no back-and-forth or basic conversation etiquette. Definitely got out of there politely and never looked back.
13. Biting Off More Than You Can Chew
I once went on a date with a guy to get Indian food and every time I spoke, he interrupted me. It didn’t stop there though: He made me watch a five-minute-long anime trailer, with no subtitles, even after I politely told him that I wasn’t into a) anime or b) the genre of the trailer he insisted on showing me.
The entire date consisted of talk about marvel movies and anime. The situation only got worse when the food arrived and we began eating. I couldn’t believe it when he slurped the white sauce. He literally raised the little container to his mouth and just…slurped it!
Of course, it made the most disgusting sound and I was nearly put off from my entire meal. I never thought that table manners would be a dealbreaker I came across in my twenties, and yet…
14. One For The Road
I matched with a guy on Tinder in 2014 while I was in grad school and new to the city. He seemed cool enough and lived in a small town about 45 minutes away. He offered to take me out for dinner and I said I would meet him there (for my own safety, of course). He not only insisted on picking me up, but he showed up with a liter of Fireball.
He promptly sat on my couch and started pouring shots for my roommate and I. In general, he seemed like a genuinely nice guy, just oddly misguided. I was not interested in binge drinking Fireball before dinner. It got worse when he ended up drinking nearly all of it and tried to hook up with me.
When I rejected him, he wanted to drive home despite being completely wasted. I forced him to sleep on my couch and locked the door to my room. We never spoke again, but he did try to add me on Snapchat about four years later...
15. A Game Of Telephone
The first date was uneventful. We talked about what we did, our backgrounds, our upbringing, and other vapid, nebulous stuff. This was late afternoon on a Saturday. We parted, but the following morning, I opened my phone—and couldn't believe my eyes. My date had sent me a barrage of messages.
She listed all the things I should have done or said better, what she found annoying, etc. I’m pretty darn hurt by the message, so I start to write what I thought: "There's no need for that! Just say thanks and let's part ways!” But instead of sending the text, I remembered to not chat when emotions are running high.
That afternoon, another message: "When do you want to try again, think it could be fun?" This time I did respond: "Never".
16. A Coming Of Age Story
I was at the mall one summer day, hanging out with some friends. I see this guy who looked like a friend of mine, so I walked up to him only to find that he was not that friend. We introduced ourselves and exchanged pleasantries. He was cute too! He gave me his beeper number (I'm old) and we planned to go get coffee sometime.
That day arrived. It turns out he worked at a Red Lobster down the road from my house so I walked over there to meet him after his shift ended. We went to go see a movie at the theatre we held hands and kissed nearly the whole time. We went to go get coffee after and we started chatting.
"What year are you?" he started. "Going to be a junior this fall," I replied. Nonchalantly, he goes “Cool, I didn’t go to college” to which my reply is “College?” So that's the story about how two strangers vastly over/underestimated each other's ages. I thought he was 17 or 18, he thought I was in my 20s.
In actuality, I was 15 and he was 25. He took me straight home and we didn't go out again.
17. Out Of Step
I was 25 and she was probably in her early 40s. We matched online, as one does these days. We met at a local bar that was closer to her place and a 45-minute drive for me. I thought that this sounded like a lowkey, chill date and we can see where things lead! This was not the case.
The bar was definitely an older crowd than I was used to, but I quickly melded right in—or so I thought. I get our first round and the bartender looks at me a little questionably, but I didn’t think twice. As I return to our seat with the drinks, she begins to pump up her ego, talking about her hair and how good her butt looks for her age.
Being 25, I didn’t mind where this conversation was going. We continued to chat more and as the drinks flowed, she began to get more and more overtly confident. At one point, she got out of her seat and started dancing cumbia style, regardless of the fact that the music in the bar wasn’t close to this genre and didn't warrant any hip-rolling moves.
But here she was, turning around and around, showing me the butt she was so proud of. As if this wasn’t enough, she repeatedly tried to get me up to dance. At this point, the entire bar was staring as I politely declined.
As more and more people started watching, I decided to get up, use the restroom, and text my buddy because I knew I was probably going to need an escape plan. On my way back, I make my way to the bartender to ask for more drinks. He tells me they're on him because it looks like I have my hands full.
I return to my seat and my date tells me a guy approached her to ask why she's with me. I shrugged knowing this would probably end awkwardly. The night dragged on and she continued to gush about her butt, which by this time I didn’t even care about.
She turns to me and straight up says, "You know we're not going to have sex the first night, right?" and I nearly choked on my drink. I said that wasn't the idea (well, initially I suppose it was, but after 10 minutes I just wanted to run). I called for the bill and said I'm going to head home.
And as I'm driving away, I see the guy that was trying to hit on her was outside. I rolled down my window and yelled, "She's all yours, buddy!" and drove off. At least now I have a good story...
18. My Time To Shine
Went on a date with a guy, who arrived at our first date with a literal presentation of non-negotiable demands he required from a future partner. She must be a housewife, produce two boys and a girl (in that order, gender specified), not work or desire a career, and be able to move 500 miles away to live on an acreage in his parents’ home (with them also in residence there).
And get this: his future partner could not have any male friends, but he also wanted someone who is open to sleeping with whoever he chose so he could watch. The list goes on.
He didn’t ask me a single question about my life or interests the entire date. He just spat out this list for two hours (at which point, I politely bailed). Props to this guy for knowing what he wants, but the PowerPoint guy did not land a second date with me.
19. The Price To Pay For Love
I went on a date with a girl to go to the cinema on a weekday. It was her idea, and I wasn’t too sure about it in the first place but I was willing to give it a try. She was really attractive, but something seemed off about her when we were chatting.
I calmed my worries when I thought, well worst-case scenario, I’d get to watch a movie. The cinema was on the top floor of a mall, so while we were walking there, she decided to pop into a Mac makeup store. We weren’t in a rush, so it was totally fine.
She spent 10 mins picking out a bunch of different things, and before going to the checkout, she tried to confirm with me that I’d be buying it because we were on a date. I actually kept asking her to explain what she meant because I couldn’t believe she meant for me to buy a relative stranger a few hundred quid worth of makeup.
Needless to say, we didn’t even make it as far as the cinema. I didn’t even have an argument with her. I just turned around, walked out, and blocked her number.
20. Put Your Money Where Your Mouth Is
During my big party phase, I went to a casino one night with a guy from college because it was the only place open at 1 am. I told him I was broke to explain why I only had one drink. He, on the other hand, had quite a few. It was time to leave and we got the bill, but he said he had to go draw money from the ATM to pay, so he left to do that.
I waited a while for him to come back, then I went to the ATM to find him and couldn't. So, I texted him asking where he was and he just sent me the emoji with the tongue out. Because I couldn’t pay, the staff at the casino detained me in a room and took my ID. They were very harsh and interrogated me.
In the end, my dad had to drive through at 4 am to pay the bill so I could leave. I'm now banned from that casino, thanks to this awful first date.
21. Just What The Doctor Ordered
A friend set me up with a guy who had similar interests: He worked in healthcare and was big into fitness. We went on a date to a restaurant where he starts telling me that he could’ve gone to medical school like I did—if he really wanted to.
Instead, he liked being Nurse Practitioner because “being one of the only straight dudes in nursing school got me laid a lot”. The rest of the date consisted of him either telling me how lazy doctors are, or how he was going to spend “our money” once I became a practicing physician. The cherry on top?
During the course of this delusional conversation about “our” future, he began to eat off my plate and had the guts to imply that it wouldn’t be very ladylike if I finished my plate myself.
Needless to say, I was just waiting until he could drive us home. I never spoke to him again. He was surprised when we ran into each other at the gym a few months later because he thought the date went so well...
22. Take My Breath Away
In high school, I went on a date with a girl I met through a friend. We had been texting for a while and seemed to really hit it off. She brought a (girl) friend along because even though we’d been talking, I’m still a relative stranger to her. And that's when the date goes off the rails.
To my surprise, a guy crashes the date, chatting casually with everyone present, and as he sits beside the girl I’m there to see, he offhandedly refers to her as his girlfriend. I was too awkward, shocked, and hurt to say anything, and left soon after.
We texted later and when I asked about it, she said, “He probably just said good friend". That quote has stuck with me. Maybe something else was going on and the guy was someone she had tried to get rid of. Maybe I missed some cues. But at the time, it felt like a really bad cover...
23. No Sweat!
He and I went out on a lunch/tennis date. Lunch was fine and he seemed alright, so we went to play tennis afterward. After nine games in 80-degree weather, we were absolutely sweaty and gross, which is not normally what you’d want on a first date.
Surprisingly, he immediately comes over after the last game and gives me a wet hug, but it doesn’t stop there. After the gross hug, he leans down and kisses me with his tongue down my throat!
I had to push him away, totally grossed out by both the sweat and the tongue, and had to awkwardly tell him to his face I wasn't into him and I didn't want him to kiss me again. I have yet to go on a first date that tops that one in cringe-level.
24. Hit The Ground Running
I met a woman on a dating app who seemed nice enough. But she was in country A and I was in country B, so we really couldn’t see each other. I was a little annoyed at that, but kept chatting a bit just to get to know her.
Eventually, I made it clear that I wasn’t looking for an online relationship, but if she ever came to my country, she could look me up and I’d show her the sights! When she replied, she made it sound like she might visit soon, so I gave her my phone number.
This all happened over the course of two or three days. Strangely, I get a call at work about a week later. I was surprised it was her, and asked if she was here already. “No,” she said—she wanted to know if I was really serious about our relationship before she moved here.
What? We don’t have a relationship. I was just going to show her the sights and take her out on the town if she visited. Instead, she tells me she was preparing to move here and then goes on and on about my commitment to her! I reviewed our chats and couldn’t see how she got the “committed relationship” idea, at all.
I told her to never, ever call me again and blocked her on the app. What a bonkers situation...
25. Gimme A Break!
When I first moved back home from college, I went on a date with this guy I met online. We met up and I have a habit of telling my parent "I'm going out, I'll be back later" without any specifics. But this time she replied, "Just be careful and if he can't drive, get out of the car".
We were en route to our first destination and it was closed. So, he asked me where I wanted to go and I said, "Hooters and bowling". I know, I know—classy. Anyway, we ended up going across town because he wanted to take me somewhere. But by this time, I've determined I'm not into him, so I just go along with it. Maybe we can be friends, right?
His brakes give out and we end up having an accident. We ran into the back of a truck pretty hard and I jerk forward, glasses flying off. After the smoke settles, I start laughing because it’s what I do when I’m nervous. He asks if I'm okay, and I said sure.
I'm looking for my glasses and he goes, "Oh this is bad, really bad". So, I said "Why? No insurance?" His response makes my blood run cold.
He says, “No, I have a warrant for my arrest". He gets out of the car and runs. As he's running into the sunset, he's yelling back at me "I'm really sorry, I can't afford to go to jail again". The person we hit, leaves. So, I'm the only one there and the police show up.
I had to call my parents to come to pick me up and of course, I gave the cops his info. The authorities gave me a ride to a gas station across the street as I was waiting for someone to pick me up. I leaned back, took a picture in the cop car, posted it on Facebook, and tagged him in the picture.
Somewhere in between the running, he found time to get on Facebook and block me. The worst part about not just the accident and the whole fiasco that followed? I didn't even get a chance to enjoy Hooters and wings.
26. A Sticky Situation
We scheduled a movie date at 4:00 pm on a Sunday. I bought her a ticket and waited until 4:10 pm before texting her that I left her ticket at the booth and went in to get seats. She shows up thirty minutes late and promptly fell asleep once she sat.
After twenty minutes, she threw up all over the place and ran off to the bathroom to clean up. When I follow to help, she throws a fit and tells me to stay, to watch her purse and the movie. So, I sit in a different seat to avoid some of the mess. She comes back and falls asleep with her head on my lap.
Everyone within a five-seat radius of us moved because the smell was still absolutely horrid. I found out she went to an extended bottomless mimosa Sunday brunch (a cultural staple in my city). Ten minutes later, it happens again. This time she stays where she is.
My pants and shoes have been soiled. I wake her and tell her we are leaving. She demands we stay because she doesn't want to ruin the movie. I say we are leaving right now. She gets loud like a dying animal and refuses again. People hush us and she falls asleep with her head on my lap.
Any movement or effort to get up results in loud animalistic whining. The movie ends and the lights go on and we finally see the mess. It's everywhere. The seats in front of us, the floor, her clothes, my pants, my shoes.
We leave quickly. Halfway out the door, she announces that I forgot her purse. I spend about ten minutes looking for it before an usher brings it to me, dripping in bile. Going by the strike system, she’s lucky I even retrieved the purse.
To recap, she was late for the movie, puked on me, refused to leave, said "I" forgot her purse, and didn't even invite me to bottomless mimosas on Sunday funday.
27. Driving Me Nuts
I once went on a date with a guy who couldn’t stop talking about self-driving cars and how they’ll save us in the future. I questioned the idea that they were better than human drivers, simply because I didn’t know much on the subject to have a fully formed opinion, and he made me regret this decision for the next hour.
He then insisted that no matter how good a driver I was, a computer would always be better. I kid you not, the entire date was spent talking about solely this subject. To this day I hate any mention of self-driving cars, solely because of him.
28. Face The Music
I went to see a band play at a record store with a girl from my business class. The date started off rocky. So the guy at the front is counting our change, she laughs and goes, "This guy definitely isn't in business school," directly in front of him...I gave her a brief look of disgust and continued to the band.
For the rest of the night, she scanned through records while I danced to the band in the other room. I think she knew at that moment as well that we weren't compatible, because I definitely did. I was turned off by the fact that she was so disrespectful at the beginning, and I didn't entertain it at all.
I ended up giving her a ride home, but we definitely never went on a second date.
29. Read Between The Lines
I once went on a date with a guy who opened by showing me his of a demonic jack-in-the-box. We were in a bookstore, which was a date location that he picked out. I foolishly thought we might have an interesting discussion on reading, but turns out, he rarely read and it was just the only place in my city he was familiar with...
You don’t need to hear the rest of the date to know how it went...
30. Everybody Makes Mistakes
I met her in an adult soccer league. One day, I asked her to grab breakfast that upcoming weekend, and she accepted. That weekend, I took her to a hole-in-the-wall diner, and throughout the meal in this public space, she talked about all the inappropriate things she was into exploring.
She went on and on about breath play, being dominated, whips and cuffs—the whole nine yards! I got the check, but immediately realized my wallet was in my gym bag from the night before. I apologized, and after she paid for us both, I took her back to her place.
She invited me in, and I couldn't refuse because she had just bought me a meal. An hour later, after the nastiest hookup of my life up, we were lying in bed when she gets a text and starts to panic.
"Oh my god, you have to leave! My boyfriend got off work early and if he finds us, he'll kick me out!" This is the first I'm hearing of a significant other, and I realize that I just slept with a lady on her boyfriend's bed after she bought me breakfast with money that he gave her...
So, I throw on half my clothes, jump into my car, and knock over the mailbox in my rush to get the heck out of there. When I get home, I see that my rear bumper has a nice new crack.
31. Through Rose Colored Glasses
I was really young, probably about 15 or so. I was boy-crazy and had a crush on every guy who remotely expressed any interest in me. The boy I went out with was named Jesse. We met through a mutual friend, and while he wasn't exactly my type, he told me he thought I was pretty and so, I wanted to give him a chance.
A couple of weeks after we met, we decided to meet up at the mall for our first official date. He was very sweet and we held hands—typical teenager stuff. But then he got weird—super weird.
We're sitting on this bench and he turns to me and stares at me right in the eyes and says, "Wow, when I look into your eyes I feel like I'm looking into your soul". Okaaaaay. I'm fifteen and desperate for an epic love story, so I just smile.
He goes on, "I know this seems soon but...I think you might be my soulmate. I can't wait until the day we can get married, and have babies, and live together. We're going to have such an amazing life together!"
So let me recap. I'm fifteen, I'm on a first date, and my date essentially proposed to me at the mall...
32. Coming On Strong
We had been talking on Tinder for around six months. Our date went really well and he was super sweet and chatty! Right at the end, he said, "I thought your profile pictures were beautiful, and you're even more beautiful in person".
I thought wow, that's a lovely thing to say! Until he finished his comment with, "And your breasts are even bigger than I thought! Are they still perky, or have they started to sag?" The waitress was standing next to us. We both just stared at him then I asked for the bill, paid it, and left.
33. Bang For Your Buck
I went out for dinner and a movie with a guy. I tried to chip in money at both places, but he insisted that he cover it all. At the end of the night, we're sitting in his car in the parking lot of the restaurant we had just eaten at, and he flips the script.
He motions to his lap in a suggestive way and says, "I mean, I bought you dinner and took you to a movie, it's the least you can do". Thankfully I lived nearby. I hopped out and walked home.
34. “I Wanna Be Your Lover”
I was a barista in a café during college and this loyal customer asked me out. He took me to sushi and then to a bar and where he bought me a drink. The conversation went well, and even though it was nothing spectacular, he was cute, intelligent, and funny.
When he takes me home, he parks outside of my house and assumes he's coming in, which I shut down immediately. Genuinely confused, he asks why not. He says he did everything right, he bought me dinner and a drink, so he should get to come inside because that’s how these things go. It doesn’t just stop there.
Then we start arguing about it and I start to worry that he's going to just enter my apartment whether I like it or not. He proceeds to put on a Prince CD. Confused, I ask why he’s putting this on in the middle of our argument. He responded, "Here, just listen to this, Prince is sexy! All girls like Prince! It’ll get you in the mood”!
I think I may have actually ran away when I finally got out of his car.
35. Get A Move On
I once met a girl on a dating site. We chatted for about two weeks and got along pretty well! Surprisingly, she invited me to come to her place for a date. But when I get there, I see a huge U-haul truck outside. Perhaps a roommate is moving out or arriving to move in?
Turns out, she’s in the middle of packing up and moving to another state, and wanted help with the heavy lifting. None of this was mentioned in any of our conversations over the previous two weeks, by the way...
When she made it clear she was the one moving, I just said "Well, good luck with the move then!" and got the heck out of there.
36. A Real Nosedive
I made plans with a guy I knew from a charity I was on the board of. He took me to a chain Mexican restaurant. I pulled up a few minutes early, but my dad is a pilot of a plane and was going to be flying overhead the restaurant so I wanted to see him fly over. At 8:00 sharp, the guy calls me and tells me that I am late.
I try to explain the whole flyby thing, but he isn't having it. We go inside and I try to order some food, but he tells me that we are not getting food and that I can't eat. Almost immediately, he begins ranting on major political topics which I'm completely opposed to. I ask him if this is all a joke or if he really is he is being serious...
I finally convince him to at least get an appetizer, which I was not allowed to choose. He got guacamole (table side) but only had them put onions in the avocado... I was planning my escape when he asked, "Are you figuring out how you are going to leave?"
Yep. Thanks for the one domestic beer and scoop of plain guacamole. See you never!
37. Let The Cat Out Of The Bag
I went on a Tinder date with a guy who I seemed to get along with well prior to the date. We texted and talked on the phone, then arranged to meet at a restaurant/bar. He was cute, but seemed bitter. I soon found out that he was from California and apparently didn't like this new city we were in. This was because everyone here is uptight about sleeping around.
During the date, he not only ranted about the prude-ish nature of our city, he also invited the waitress to a party that his company was throwing. This was after sending back the french fries he ordered. Then, when I showed him a picture of my dog that I had on my phone, he too took out his phone.
However, instead of a pet photo, he showed me the most inappropriate thing ever: A picture of his member.
We walked out of the restaurant together to get our cars from the valet. My car came first and I left, thankfully. However, he texted me later explaining that he had my sweater (apparently I dropped it on the way out) and if I wanted to see it again, I'd have to hang out with him.
Rest in peace, sweater...
38. Bend Over Backwards
When I was 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 normally don’t pick up on athletic skills very quickly, but I wanted to try and impress her somehow. So, I showed up and gave it my best. Well, I hugged the wall the whole time and made a fool of myself.
The highlight of the night was when I saw a flash of light just as I fell in front of a group of people. It turns out, I had fallen right at the exact moment someone took a picture, so my failure was immortalized forever. My date took me back to my apartment and ended the relationship before it began.
On the bright side, the woman who is now my wife was at that ice rink on that night. We didn't realize we were there the same time until a year or two into our relationship and she exclaimed, "You were that guy who couldn't ice skate! Yeah, your date didn't seem that into you..."
39. A For Effort
I met a guy from OK Cupid who seemed nice, but never stopped talking. After interrupting me for the third or fourth time, I finally asked him, "Do you want to hear anything I have to say?" He apologized profusely and then pulled out a pad of paper and a pen.
He then proceeds to jot down notes as I'm telling him about myself and my interests. I finally ask him what he's doing and he says, "Oh, I'm writing down things I want to tell you when it's my turn to talk again". A strange first date, to say the least...
40. Mr. Not-So-Right
She criticized absolutely everything: the car I was driving, the clothes I wore, my cologne...We were supposed to go bowling, have dinner and then have some drinks. When an attendant came over to ask if we wanted anything, I ordered my snacks and asked if she wanted anything. Her response floored me.
She said, "You mean you don't know? What kind of date is this?" And then halfway through our game of bowling, she mentioned I was bringing up the wrong conversation topics. Thankfully, my brother called me out of the blue asking to borrow some fishing gear and I played it as work calling me in.
I couldn't get out of there fast enough.
41. Delusions Of Grandeur
She kept talking about how life was supposed to be "enjoyed to the maximum". She spoke about how she spent lavishly on expensive Italian, French or Japanese dinners and trips, which would consequently leave her broke and constantly borrowing money from others to sustain her lifestyle. She considered it "classy". I considered it delusional.
To her, life should be spent on only the best and those who couldn't paint the town red were tasteless and ignorant peasants. Yet the irony was that she couldn't earn enough to maintain her lifestyle. Honestly, I might not have been so annoyed if she had been from some downfallen royal bloodline because it might have made more sense then...
Unsurprisingly, I ran for the hills, as fast as my legs could carry me.
42. The Trials And Tribulations Of Casual Dating
We had agreed earlier that week to a date, and I'd pick her up at around 8 pm from her place. I call her around 7:30 pm just to confirm that she's ready, but she doesn’t pick up. Call again at 8:15, no response. Text her, no answer. At this point, I had been stood up and I was basically over it.
Went to a bar by myself to eat and drink in shame. Out of the blue, a great friend calls and says, "Hey man, I've got two girls with me if you want to hang out with us three"! No better way to get over being ditched, right?
So, I meet him at this great bar and we're having a blast. I walk up to the bar to get drinks and had to do a double-take. It's her.
The girl who ignored my texts was sitting at the bar with this admittedly taller and better-looking guy who had an Australian accent (no hate to my Aussie friends, but over here, it’s basically a panty-dropper for college girls). So I casually walk up and say, "Hey guys! How’s it going?” The look on her face was priceless.
They both ended up slinking out of the bar after I forced a really awkward conversation. At that point, it was pretty comical to me, and had already determined I was done with her, so I had a little fun with it. She called me three weeks later to "hang out". Denied!
In the end, I just chalk it up to the stupidity of casual dating. These things happen, I hold no grudges, we all do dumb things because we're selfish at times. Life goes on!
43. Just A Heads Up
I once took a girl to movies, which I now realize is not the best location for first dates.
She asks if her best friends can join us and there goes my chances. Trying to be nice and assuming her friend is another girl, I say yes of course! Shows up with her friend, who is indeed a guy. This is when I find out that it's her one and only ex.
Trying to salvage our date, I go to pay for my ticket and hers, and right afterward, 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—they are best friends.
When I get home the guy adds me on Facebook, and he proceeds to tell me not to bother trying to date her, she's a terrible girlfriend. Thanks for the heads up, pal. Take note future daters, taking your ex-turned-best-friend on a first date is a bad idea...
44. Empty Handed
I went on a date with a guy who seemed really cool at first. But my opinion of him deteriorated as it went along. First off, he told everyone we encountered that we were on a date. Everyone. And at the end, he told anyone he could find that the date went “splendidly”!
At one point, he asked the waitress to make the date more romantic, so she brought out a giant ice cream sundae that was meant for two people to share. However, my date ate it all by himself and managed to spill ice cream all over himself. Very attractive...
After asking me if I was a gold digger and explaining that he makes a truckload of money and needs to “protect” himself, he demanded separate bills. Fine, no biggie. However, all four of his credit cards were declined. He asked me if I didn’t mind paying and told me (hilariously) that he would get the bill next time.
There would be no next time. At the end, he gave me stickers of his welding company as a thank you for paying the bill, since his credit cards must have all simultaneously had some kind of error...
45. Is She Swipe-Worthy?
I didn't have much of a chance on this date because I was hungover badly from the night before. He took me to the university dining hall for dinner, which wasn’t great but it wasn’t too awful. What I couldn’t believe was that he didn't even offer to pay even though he had a universal dining card, so the meals would have cost him $0.
This was also before we went to a show. It got worse when we got there two hours early. We just sat there, watching the band set up in silence, not talking to one another at all.
46. A Walk Of Shame
I had a very disappointing date in high school. It was the heart of winter and around -40 degrees Celsius. We had gone to a movie and it was so awkward.
She didn't seem to want to be there and was very detached. After the movie and a bus trip home, she admitted that the only reason she agreed to the date with me was because my friend had turned her down a few days prior. I wasn’t aware of this.
Discovering that was a pretty big letdown, confirming that the date was a definite waste of time. But I figured, I'd head home, and make the best of the rest of my day. I got off the bus and wanted to get home as soon as possible.
At the bus stop, there is a thigh-high railing around a nearby parking lot, and instead of walking around it, I decided to step onto—and then over—it. The second I stepped onto it, I realized I'd made a huge mistake. It was coated in ice.
I Charlie-Browned and flipped into the air, losing everything in my pockets and ripping my pants from my butt to my zipper. Not to mention that I fell down right onto the railing with my shin, fracturing it. It's still - 40 out and I can't just lay there until help comes.
So, I fish around in the snow, grab my stuff, try to stuff my parts back into my pants, and stagger home, balls in the wind. A memorable day, to be sure.
47. Straight Out Of A Sit-Com
I once had the weirdest encounter that turned into the strangest first date. One day, I received a text from a number that was one digit different than my own. It read, "Hey number buddy! I'm in a town two towns over from you! Where are you?"
After some bemused back and forth we established that we were both single, and so she wanted to meet up. Since I didn’t want to meet a complete stranger in just any place, I suggested a café in the town between ours, and we arrange a date.
At this point, we have no idea what the other even looks like (this was around 2004, before smartphones or Facebook). So, we meet at the café and she seems nice—fun even! But then it takes a turn.
After a quick chat, she says, "So, your place or mine?" Considering we’ve just met, I suggest chatting some more at the very least! And her response was: “Don’t you want to sleep with me?” to which I reply, “Lady, I barely know you!”
So, she sat with a pout pasted on her face and refused to even speak to me after that, which was as awkward as you could imagine. After a very confusing couple of minutes of wondering what the heck was going on, I eventually say that I’m sorry this didn’t work out and walked away.
She never messaged me again. I still can’t believe something like this even happened...
48. Taking You To The Cleaners
Back in my extremely-lonely-and-no-standards phase, I went on a date with a guy who wasn’t my type, but I remember thinking that types are bogus anyway—and it might just go great! Long story short, my optimism got me nowhere. The date was in fact not great.
We went to a restaurant that I suggested because I knew the menu and could afford it. I ordered an enchilada and he got nachos. I thought things were going well until he started complaining about how expensive the food was and how gender norms expected him to pay.
I was okay to cover, so I paid at the end of the meal. But even after we left, he complained about the price of my enchiladas—the second cheapest thing on the menu. Then he asks if I'd like to go for a drive because he's got a special spot. So we're driving for about forty-five minutes.
I'm not panicking because he seems harmless, if just a bit rude. But hilariously, he spends the whole drive talking about how much money he makes at his job. We finally pull off the highway and I'm so excited to see what he has planned. To my surprise, we drive into a car wash.
Luckily, I adore automatic car washes, so I was kind of keen! But then he parks in a self-service bay and takes another 30 minutes to hand wash his car while I just sat there, by myself, in his car. When he got back in, he wouldn’t stop talking about how much he loved his car.
Okay, maybe it was a good car—I've got no clue. As if talking my ear off about his car wasn’t icing on the cake, he then proceeded to do a burnout in the car park, while laughing like a jackal. By this point, I was more than a little annoyed.
Next, I suggest a nice park down the road from my house where we could talk. That way I'd have a quick getaway if I needed to leave. Instead, he drives me to his favorite park, which turns out to be the most secluded park I’ve ever seen, consisting of a picnic table, sad grass, and a lone rusty swing set.
Again, making the best of a bad situation, I go to the swings and try to have fun. Casually, I ask why this is his favorite park. Maybe it has sentimental meaning to him. Maybe he likes the river. Who knows? But no, it's because at night this park is a well-known dogging spot and he wanted to know if I was keen.
In the same breath, he launched into a tirade about how he was a nice guy and everyone on [the dating app we met on] wouldn't give him a chance.
Considering he hadn't asked me anything about myself, complained about the restaurant, took a 45-minute joyride to handwash his car, and then took me to the middle of nowhere to visit a dogging park where he talked my ear off about how "bitches" are "frigid," he shouldn’t have been surprised when I said that no, I was not keen.
49. Second To None
My roommate had met a girl online, talked to her for about a week and set up a date. They were to meet at the mall and go to a movie across the street. Sounds fine and dandy, right? Well, I went with him to the mall (because I had to pick a few things up anyway) and we split. 10 minutes later, he called me in a panic.
It turns out the girl he was meeting had invited along two other guys that she also met online. Apparently, she only had one free day a week and wanted to “explore her options”...
50. Some Funny Business
I was on a date with this girl who seemed great. She was good-looking, funny, and shared similar interests with me. It was our first date, and we were sitting in some bar that she's a regular at, when we start 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 pulled out a red 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 only a week and this was the first date. On a first date, aren’t you supposed to try to impress the other person? I put the clown nose aside because she was good-looking, and I wanted to hook up.
"Oh! That's so cool. I didn't know clown school was actually a thing,” I responded. "Oh, it's competitive,” she said. Continuing that line of thought I asked, "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.
Sources: Reddit,
