People Share Their “Oops Moments” During Their Dates

Having to be invited on a date feels like a fairytale for some people. However, it still depends on how the date would end. The result could be either a second date or none at all. 

Well, these people from the Reddit Community shared their most embarrassing, horrible, weird, and dumbfounding date moments. Check these out!

1. Party Date 

Freshman year, this guy who'd been in a couple of classes said he wanted to take me out on my birthday. He ended up taking me to a "party" at his friend's crappy apartment.  

Then, about five minutes in, he tells me he has to pick something up, but he'll be back soon. Two cups of stale keg beer and three hours of awkward small talk later.

Well, he shows up not being himself and tripping on a combination of substances. Completely forgot I was even there. I walked myself home that night.


2. Tired Guy

I was seeing/dating this girl I worked with and had plans to go for dinner and drinks on a Monday night after work. Mondays at work consisted of me starting at 4 am and doing a stock take, taking in the delivery, and finalizing stock. 

On a good day, finish by 11 am. This day, however, I finish at 6 pm. Anyway, so I finish and have a miserable beer in the bar down the street, then meet the girl. 

I. Am. EXHAUSTED. But I like her, so I power on through. We sit at a table and start chatting. Our drinks arrive, as does some water.

And then I yawned. Really loud. And stretched my arms out. And knocked a potted plant over. That knocked a menu over. On to a candle. Setting everything on fire.

And I am OBLIVOUS of this happening. I only realized it when a guy at the next table dumped a glass of water on it. She's laughing. I'm mortified. 

The guy is looking at me like I'm a moron. I get up to get another drink, and I get one for the dude at the next table. Set it down and went to shake his hand in thanks and KNOCKED THE DRINK ALL OVER HIS DATE!

I apologize. Offer to pay for dry cleaning and sit down. Mortified. We skip dessert and go home. I've never been more embarrassed. Worked out in the end, engaged to the same girl!


3. Wrong Spot

My boyfriend and I went to a pretty casual seafood restaurant for our one-year anniversary. We never really got the chance to go out, so this was still pretty special. 

The food and service were great. I can always tell, however, when my boyfriend needs to REALLY GO to the restroom after a meal. 

Well, he got up and bolted away from the table, so that was an obvious hint, too. Got back around 15 minutes later, informing me we had to leave. Now. 

It turns out there was only one stall and a urinal in the men's room. There was a waiter taking forever in the stall, so my boyfriend did what was (I guess?) necessary... He dumped it in the urinal. Definitely not going back.


4. Pointless Stories

We meet at the restaurant. She is a little more rotund than her pictures suggested. Whatever, I think, I'll stick it out.

The conversation is terrible. She tells me about her tiny dog, Peanut, and about the peanut she has tattooed on her foot.

She talks about the Steelers and how they're superior to every other NFL franchise. I do not like the Steelers. I do not care about the Steelers. I express these opinions. She is relentless.

She conducts the date as if it is a job interview as if she is vetting me for a position. Maybe we'll be getting married in a few weeks. I do not enjoy this.

Then, she tells me about her roommate’s personal life. And how, on Friday, her roommate couldn't make it and asked her (my date) if she could cover for her. She could.

So she meets this guy and tells him up front that she will not sleep with him. He proposes something horrifying, and she agrees. At this point, we had been sharing the same physical space for a total of about 40 minutes. And she's telling me this.

I pick up the check and walk her to her car, just trying to be a nice guy, not really sure what to do at this point. We get to her car, and I'm being really awkward, and she can definitely tell that I'm uncomfortable.

So, naturally, she kisses me on the lips and invites me back to her apartment. I decline. I kind of wish I had said yes. It would have made for a better story.


5. Too Many Warnings

My first internet dating experience: I went to her beautiful but poorly maintained home and rang the bell. No answer. Lights were on inside.

I rang again, but still no response. She had told me her ex-husband was a psychopath, and she had an advanced degree in psychology, so that seemed more than divorcee bitterness.

I dialed her home phone and could hear it ringing, no answer. I tried the door handle. I was surprised it was unlocked but still more surprised when the burglar alarm shrilled out wooo-wooo-wooo...

It sounded for a few minutes, and I pondered my options. I decided to ride it out and sat on the hood of my car in her circular driveway. I could hear the phone ring inside. That would be the call from the alarm service.

I sat another ten minutes waiting for the police to show. A squad car pulled up the street, stopped at the bottom of the drive, and lit the scene. I stood with my hands outstretched as a pudgy patrolman walked up the drive in silhouette with the bright lights of his car behind.

We had a brief conversation as I explained the situation. He told me he was waiting for backup before going in. As we waited, he turned to me and said, "Mr. Frowawayduh, you seem like a really nice guy. Can I give you some advice?" "Sure," I replied.

"This isn't my first time here. Run, don't walk, run away from this woman." He made the glug-glug hand motion that means "She drinks."

The other officer arrived, walked up to the front door, and stuck his head inside. He shouted, "Dr. Drunkard, it's Officer Smith again. Are you okay?" A slurred "Yes, offisher!" sloshed out. "You can go now, Mr. Frowawayduh." She called a week later to try again, and I said no.


6. Crazy Hot Guy

Met one of the hottest guys I've laid eyes on. We shamelessly flirt in line at the store and exchange numbers. I'm on cloud nine.

Agree to a date after I get off work one night. Picks me up and takes me to his house in a decommissioned cop car with an open container.

He pours wine when we arrive, demands to buy me new shoes, and throws pictures of him and his ex-girlfriend at me. As I got up to leave, he threw his wine glasses on the floor and told me that I couldn't leave and I couldn't call a cab since there was no reception where we were.

He tries to block the door, but I wriggle through his arms and the door jams. I run 2 miles down a dark road until I get cell reception.

I called a friend and hid in the bushes on the side of the road until I got picked up. Oh, he calls me the next day, leaving a rambling 2-minute message, in tears, weaving between apologizing and demanding I call him back.


7. Ruined Excitement

I'm not sure when this happened, but it was sometime in high school. I had a crush on this out-of-town girl who moved to my little po' dunk town.

Of course, not being from there, heartthrob ensues. She IMs me (Yes, this story is that old.) and asks if I wanna come watch a movie.

We figure out what we're gonna watch, and I head over. Her parents are gone. Her siblings are gone. Exciteddddd, we begin watching a movie. She gets a phone call. It's one of my favorite movies, so I don't mind waiting for her.

The movie ends, she's still not back. Turns out she was talking to her recent ex-boyfriend- a friend of my brother's. When I went to her room to check on her and let her know I was gonna see myself out, I found out she was making out with him. Soooo... yeah.


8. Greatly Offended

I met someone online roughly 12/13 years ago, and we had an absolutely adorable, lively email exchange for several weeks. I was traveling for work, and he was taking his comps for his Ph.D., so we couldn't meet sooner.

After dozens of emails that I looked forward to immensely, we met for coffee to celebrate that he was officially ABD. Minutes after we meet, he's very nervous and sweaty.

As a fellow introvert, I just assume it's social awkwardness, writing it off. I give him some cheesy card from Hallmark, congratulating him on getting through his comps.

At this point, his behavior gets increasingly more jumpy, as the card upset him. He talked in truncated sentences and seemed to be looking around a lot.

All I thought was something was really wrong when this witty, bright guy was struggling to keep up conversationally. He's even sweatier. Eventually, he stops making eye contact.

About 15-20 minutes after first saying hello, he says accusingly, "Is this a joke?" I have no idea what he's talking about, and he storms off. I sit there confused for a few minutes, slink back to my car, driving home, wondering what the hell just happened. It was crushing.

Shortly thereafter, I received an absolutely vile email from him about why he doesn't appreciate being messed with and why he thinks I'm a horrible person. I didn't even reply because I was so confused/hurt by what had happened.

A few days later… I received a multiple-paragraph apology. He thought I was a colluder and part of an elaborate prank/deception by a fellow student in his department.

They had been pulling increasingly complex and cruel pranks on one another. He claimed that he found me too attractive to be the person he had been emailing, so he became paranoid and jumped to the conclusion it was a prank. It wasn't.


9. A Red Siren

Met a guy. He was drunk. I was drunk. We flirt. Exchange numbers. Decide to go on a date the next evening. We meet up for a standard first date: dinner and a movie.

While we're at dinner, he gets a phone call. "Hey, man... muffled voice... Nah man, she's cool... muffled voice ... Yeah, thanks, man. Talk to you tomorrow. Catch ya!".

After hanging up the phone, he then proceeded to tell me, in the kind of arrogant tone that would rival Charlie Sheen, about how he'd forgotten what I looked like, so had concocted a genius plan to have his friend call him and offer him an out if I "wasn't in his league."

I was shocked. "Oh, but it's ok, babe. I guess you're kind of cute." Um. What? From what I've learned so far, you're unemployed and hate your life. Still, you love sitting on your ass every day collecting Centrelink (Aussie welfare/dole).

Needless to say, I didn't see him again. Oh, and then there was the guy who refused to let me leave his house after we watched a movie together.

Sure, I like a guy who takes charge, but pushing me up against a wall and blocking the exit on the second date is kind of a red flag.


10. The Sad Boy

I was around 19, had just been broken up with, and was alone at an out-of-state college, so I resorted to internet dating. I met a guy who wasn't super attractive, but I thought from our emails that perhaps he had a good personality, so we met up for frozen yogurt.

The entire unbearable hour was him talking about what a loser he was--his words. He told me how lame he was for living with his parents, going to community college, and not having any ambitions or life goals.

The only hobby he had was playing the bass--he and his friends would "jam" in his parent's garage. It was very weird how he kept bringing up "jamming."

All he could talk about was how he was such a loser. I have self-esteem issues, but it was just too much to warrant a second date.


11. Overtime Couple

I told my girlfriend it would be a romantic idea to get up uber-early and watch the sunrise together, forgetting that neither of us was a morning person.

She disliked the idea but wanted to encourage me to come up with other, better ones, so she agreed. We half-consciously sat on a snow-covered bench in the dark, each trying to make sure the other stayed awake.

After about a half-hour, we realized it was too cloudy. The sun had already risen, and we didn't see a damn thing. We parted ways and went back to bed.


12. Man Down

My first time using a dating app, I met a guy who was new in town and wanted to meet different people, so he asked to take me out to a restaurant of my choosing.

The date comes up, and we go out to a small Italian restaurant. He's a little chubbier than his pictures, but it's no big deal. The conversation was a little stale, but what do you expect from a blind date? Anyway, we decided to head to the beach, which is 10 minutes away.

We sat there and talked for a little and finally started kissing, and it was going alright. Decided to try and push my luck further and instantly realised how receptive she was. Jackpot!

About five awkward minutes later, we went back to the car, and lo and behold, it wouldn't turn on. He left the lights on the whole time, and we ended up having to call AAA to come jump his car. We sit in silence the rest of the way home. Needless to say, there was never a second date.


13. Revenge Pet

Didn't realize she was using me to get back at her ex. I went to her place. She spent two hours on Facebook talking with her overseas roleplaying boyfriend.

They both discussed being vampires or something. Then she spent another two hours on YouTube looking up Jensen Ackles tribute YouTube movies.

Lo and behold, she dumped me not long afterward. I mean, okay?? Well, I just really hate my 16-year-old self up until this day.


14. Lost In The Dark

I got talked into taking my sister's godmother's niece out on a date when I was in high school. We went to see the movie "Cast Away" at the theater on opening weekend. I made the mistake of telling her to go and get us seats while I went and got snacks.

After getting everything, I came to the realization that I had no idea what she was wearing, distinguishing facial features, etc, and I was blanking on her name, to boot. I ended up standing by the theater's entrance with everything in my hands for about 20 minutes in the hope that she would see me and wave me over before giving up and sitting down in the rightmost seat in the front row for the remainder of the movie.

She eventually found me after the movie (I was her ride home), and we laughed a bit about it. Never spoke to one another after that disaster.


15. My Preferences

The day after, I first signed up for an online dating app. I was pretty gung-ho about actually meeting people and had not yet been disillusioned by the whole thing, so when a guy I'd only exchanged 2-3 messages with suggested that we hang out later that night, I was game.

He warned me that sometimes people think he's gay when they first meet him. "No problem", I think. I know plenty of people who might be misconstrued as gay for one reason or another (voice, mannerisms, they were in theater in high school...whatever).

But it was difficult to make a case for how this dude was anything BUT gay. We met for coffee in the gay neighborhood of an already pretty gay city.

His fingernails were painted pink. He asked me if I wanted to go to a gay bar or a straight bar. His three best friends are gay dudes named Sprinkles, Pepper, and Muffin.

And he was completely estranged from his family already, so I really didn't understand why he wouldn't just come out. This was on September 11th, so it was the anniversary of September 11th.

We wandered around the canals of the rich part of the city, and fireworks started to go off. It would have been sooo incredibly romantic if he were straight. And if I were into him.


16. Dragged Out

Not my date, but one that I witnessed. I used to work at a movie theater, and earlier in the day, another employee was bragging about how he had a hot date to a movie after his shift was over (We were in high school, so he was probably 16).

He ends up coming in while I'm taking tickets, so I say hi and meet his date, and it turns out that they are going to see the newest Twilight movie together. About 10 minutes later, a very angry father walked in the door and demanded that I tell him where Twilight was playing. It was opening weekend, so it was in about five theaters, so I told him which ones (by far not the strangest thing I encountered at the job).

Another 10 minutes pass and the boy's date is physically dragged out of the theater by her father. It turns out she said she was going with a group of girls.

If it wasn't awkward enough that every coworker just witnessed your date collapse, he didn't have a car, so he ended up watching the entire movie alone to tell his dad that the date went well. I felt so bad for him.


17. Just Some Nervous Guy

When I was 17, I took a girl out on a date to the movies. We ordered tickets, but I barely had enough money to cover it. We then proceeded inside, where she was nice enough to buy things.

Specifically, nachos/cheese. Well, I managed to sideswipe and get the cheese all over her dress, so I panicked and started cleaning it off with napkins, which was awkward. That was great.

Then we managed to exchange items, and somehow, I wound up holding the soda...When we were looking for seats, I accidentally bumped into her and spilled soda all over the floor, Mountain Dew, to be exact.........It's not done.

I then had some massive exponential growth of gas. I farted like really loud during the movie, and (at that point, I wanted to drown myself in the nearest canal)...

So she had to be home earlier than expected so we couldn't finish the movie. On the way to drop her off home, I crashed into a tree and totaled my car....... the best night of my life.


18. Too Friendly Neighbor

Ooh! I got one! I bought a condo about a year ago, and when I was first looking at the place with my real estate agent, the hot guy across the hall was coming in at the same time we were leaving.

As a natural wingman, my real estate agent stops him, asks him a random question about living in the building, and then pretends to get distracted and wander away so the two of us speak alone.

Fast forward a couple of months. I've bought the condo and found out that my hot neighbor has a girlfriend. When I'm unpacking, there's a knock on the door. It's the hot neighbor.

I invite him in, and we're having a very normal talk about real estate prices, football, and ordinary stuff when, out of nowhere, he comes at me for a kiss....but tongue first.

Like it was already out of his mouth and fully extended as he started the approach, I called it quits at that point and pushed him out the door and across the hall to his own, at which point we realized that his girlfriend had come home from work and was waiting for him.

Over the next few hours, he knocked several times and then resorted to trying to pick up my lock (a deadbolt) with his credit card. The plus side?

He was so black-out drunk that when I told him what he did when I ran into him a few days later, he bought me a gift card to a steak house. As far as I know, the girlfriend has no idea, and I've never met her in person.


19. Two Worst Times

I went on a date with this girl I had been seeing for a while, or it started out as a date, at least.. Anyway, we were kissing, being touchy-feely the whole night, and then she just kind of mentioned she went on a date with this other dude a few days prior.

I was actually pretty crushed since I thought it was going somewhere. Anyway, of course, I asked her what the deal was, and she said, "Well, we aren't REALLY serious."

After I already took her out and bought her dinner, she dropped that on me. Just a horrible night. I cringe every time. Another time in high school, I took this chick out for ice cream just after I got my first car.

I was a nervous and twitchy kid, and she was a sweetheart but kind of goofy. She started making some very uncomfortable confessions as we sat there. I didn't really know how to respond, got nervous, and threw up.

My thought process since then is it can't get any worse than those two. Haha


20. New Delicacy

I had a crush on this girl in high school but didn't have the courage to ask her out formally, so I kept dropping "hints." At one point, she asked me if I wanted to eat dinner at her house, so I jumped at the opportunity.

When it gets close to the day of, she calls me and asks if it's okay that the dinner is freegan. If you don't know what that is, it's okay. I didn't either, but I said that's fine, whatever, and just thought it was some sort of foreign cuisine I had never heard of.

I get to her house, and after a couple of minutes of my very bad flirting, a bunch of people show up, all bringing their "freegan" foods, and they want me to help them prepare it.

At this point, I was starving, so I just wanted the food to be ready faster than anything to move it along. I got to the kitchen, where people handed me food.

They asked if I had ever eaten freegan food before, and when I said no, they explained that it was vegan food they had gotten from the dumpster.

So I proceeded to slice off warts on cucumbers and put interesting-looking fruit into the blender until we sat down to eat.

Now, if you recall, I was very hungry at this point. Seeing the food before didn't help, but I wouldn't run out now. After all this, I felt like I had gotten closer to her because she had shared that part of herself with me.

I ate more than I care to admit, and once we were done and I was ready to talk to her about "us," the doorbell rang, and her boyfriend showed up. The moral of the story: Know what you're freegan getting into.


21. Weird Trip

I don't have any really bad ones. But one time back in high school, I drove by around 6, picked her up, and asked her what she'd like to do.

Movies? Bowling? Nope, she decided she wanted to come over to my house and meet my family. So I drive all the way home with her.

We walked in, and she said hi and talked for maybe 3 minutes in total before turning to me and asking to go home. End of the date, she never talked to me again. Weird freaking girl.


22. Uninformed Individual

I didn't know it was a date. First of all, I'm a married guy and very happy with my wife (who I've been with for 20+ years). A woman from work was hosting a get-together at a bar. I attended and found it strange when no one else showed up.

I found it even stranger when she began to show unusual levels of familiarity. At some point, I asked her point blank if it was a setup, and she told me that she thought she had been "reading signals" from me.

I swear to God, I had hardly ever noticed her before and was anything but attracted to her. I finished my drink, paid for hers, and politely excused myself. It was awkward thereafter.


23. Surprising Identity

I was about 16, and one night, I got a phone call from some girl I'd never met who asked me out to dinner. I have no idea who this girl is, but she seems to know me, so I ask her some questions to try to figure out when we met.

She says she saw me at my parent's store but won't elaborate. After a while, I became fairly confident I'd never met this girl in my life. I declined her dinner invitation and told her I already had plans.

She takes this positively and texts and calls me nonstop for the next 2 weeks. I finally decided to meet this girl in a safe, public location to get her off my back. We decide to meet at the mall.

At the mall, I run into one of my coworkers. I'm thrilled to see a familiar face and tell her all about this crazy girl I'm supposed to meet. Turns out the crazy girl is her, and she gave a fake name over the phone. Whoops. Oh, she still wants to have this date? Well, I'm already here, so ok.

The date lasted about 15 minutes. To be fair, I gave her a shot. It just didn't go very well: "What do you like to do in your free time?" "I don't ever have free time." Uh

"What about for fun?" "I like to shop...And go bowling. Do you like bowling?" She can't seriously be hinting at a second date already. "Do you go bowling a lot?" "Not really, but I want to..." Goddammit.

"If you could travel anywhere, where would you go?" "I'd go see my grandparents." That's pretty normal! She wanted to see relatives she hadn't seen in a while. Let me just make sure...

"Oh, you haven't seen them in a while?" "No, I go every six months." Oh Gosh. "I meant you can go anywhere you want." "I don't want to go anywhere. I don't like traveling." Of course, you don't.

It continued like that for what seemed like an eternity. Finally, I said, "Alright, well, that was a great Cinnabon, but I'm gonna go now. Enjoy your shopping," and I hightailed it out of there. Work was kinda weird whenever we'd run into each other after that.


24. Grocery Date

On my second date with a guy I met online, we went to a Latin Catholic mass (I figured why not? It was his thing). After a very uncomfortable hour, we went to get brunch, where he disappeared for 20 min in the bathroom.

When he comes back, he's flustered and seems embarrassed for being gone so long. The conversation is stalling, so he asks for a piece of paper and starts writing out his grocery list.

I think this is a good sign he's also not as into this as I am, so I'm surprised when he asks me to come with him. I feel bad for the guy for obviously dropping a deuce earlier and being humiliated, so I agree.

On the way to the store, he sees a comic book shop and drags me inside. I feigned enough interest not to be rude while he went crazy and started buying stuff.

At this point, I'm in full-on 'abort date' mode, but I'm trying not to be rude and wimpy. I can't figure out an escape. We then go to the store, and I help him shop. Afterward, we walk to the subway and are about to part ways.

He gives me a hug and whispers in my ear, 'Thanks for today. I had a great time. And thanks for not saying anything about the bathroom. You just looked so pretty and with mass and everything...' He's got a boner. I quickly ended the hug and ran away. Yay, dating!


25. Crazy Jealousy

The dude took me to dinner with the intention of making his ex (who was a server at the restaurant we went to) jealous. I had no clue until about halfway through my salad.

He kept looking over his shoulders and keeping his eye on where she was and only acted human when he thought she was looking.

I've never felt more awkward or embarrassed. Needless to say, I ended the night by forcing harsh words through gritted teeth, then sliding my drink over until it tipped over onto his lap.

I then made my way to his ex, handed her a 20$ tip, and told her I was sorry she had to deal with THAT for any length of time. If I was uncomfortable, so she was.


26. Judged Appearance

I had been talking to this guy online for a while, so we decided to meet up. Wait, before I go on, I just want to clarify that I am a little overweight and have been completely honest about that with him.

I showed him full-length pictures, and we chatted on a webcam. He wasn't that good-looking but seemed nice enough. Anywho, we decide to meet up.

I take a 2-hour train ride and am waiting on a bench to meet him. After a few minutes, I see him. He walks straight past me twice.

Then he texted me and said he got called into work, so he couldn't meet me. I just knew he was lying. It still stings to this day thinking about it.


27. Tried Hard

Met online and started texting. Thought he was funny and friendly. Met up and found out that he was impossible to talk to.

I wasn't really attracted to him, but I decided that we could still have a fun time hanging out, except he kept stonewalling the open-ended questions I was asking.

"What's the most fun or interesting thing you've done so far this year?" "I've had a really bad year, so nothing." Then we went back to his house to check online for movie showtimes. Internet Explorer was his only browser option. Dealbreaker.


28. Worst To Go Out With

This was with my boyfriend of six months at the time, who never took me out on actual dates. He was a fairly hard-working college athlete, and I knew he didn't have that much money, so I never pushed him to take me out.

But I really love the symphony and wanted to go one time, so I planned this whole evening in the city and paid for the tickets and everything. As we're getting on the train to go into the city, he remembers forgetting to turn an assignment in and overreacts.

I tried to calm him down because there wasn't anything he could do about it at the moment, and he shouldn't let it ruin the evening. He starts to get upset at me and breaks out into a huge argument on the train in front of people while I'm trying to reassure him it'll be ok.

We get into the city, and he refuses to talk to me now. He doesn't want to go to the nice restaurant I made reservations for. I can't even remember where we ended up going. I think it was some sports bar and he just stared at the TV the whole time.

The waitress kept giving me these sympathetic eyes that made me feel really awkward and crappy. He tried to talk me out of going to the symphony, and I said I'd go alone if he didn't want to come. He came but didn't talk to me for the rest of the night.

The relationship lasted another six months. I think in the entire year, this was one of maybe three legitimate dates we had.


29. Eat And Run

A fella took me to a Chinese/Korean restaurant on a date. He had some connection with the owners, so when we came in, there was a bit of hullabaloo, introductions, and so forth.

We ordered it following his and the owner's recommendations. We chatted, and our food came. This is where things got strange. He ate like someone was going to steal his food at any moment.

He just chowed it down. I eat relatively slowly, so by the time he'd cleared his plate, I was maybe 1/32 of the way through my delicious sesame tofu. He starts in on how slow I'm eating.

Now, I'm eating even more slowly because he's making me respond to him. At a certain point, he stands up and says, "You know what? I'm just going to drive back to my place. See you there?"

I responded by pulling my keys out of my pocket and jingling them to remind him that I drove. He sat back down, muttering about walking home, while I very slowly finished eating.


30. Weird Accusations

So, my girlfriend and I headed to the macaroni grill for a nice little date night last year. On the way, I realized that I had an evil, evil dump brewing inside of me.

So, I made a straight beeline for the bathroom. I spent the next 15 minutes becoming one with the porcelain (and learning kindergarten-level Italian, thanks to macaroni grill bathroom audio tapes!).

My girlfriend is sitting alone and texting this whole time, and the waitress decides that she must be getting stood up. So the waitress comes over and says, "I'm sorry honey, I'm sure he'll show up."

I finished my monster dump and sat down at the table, and I immediately got death stares from the waitress. We ordered our food and enjoyed our meal.

I started texting my girlfriend about the death glares I was getting from the constantly hovering waitress, who then assumed that I was the worst date ever by texting, and she then proceeded to summon the rest of the waitress to point me out.

At this point, I see them standing by the kitchen area, glaring at me, and I'm starting to get peeved. They don't know my life, after all. But it gets worse.

My girlfriend had earlier insisted on paying for dinner, so when the waitress brought the bill, and my girlfriend took it, she literally scoffed at me.

I was pissed, and as we left, I snagged a crayon and drew it on the table's paper tablecloth. And that's how my worst date ever went.


31. Too Much Fun

She was a sorority girl. Met her through a friend. She and I had the same birthday and decided to go out the night before our actual birthday. 

I've only met her a couple of times before this. Anyway, I go to her apartment. Her friends are getting ready to go to a dance she didn't want to attend, so we pre-game with them. 

We leave pretty buzzed, go to dinner, and eat cheap Chili's appetizers because we're poor college kids and awkwardly talk about our exes for whatever reason. We leave for dinner. 

Both have fake IDs, so we buy more booze and go back to her apartment to drink even this time, it's about 11 pm, so we go out to some parties. She was turning 20, and I was turning 19. 

We both drank way too much to celebrate our mothers birthing us...I blacked out, and it turns out I actually threw up all over her at some point in the night. Woke up in my bed naked with a Papa John's pizza bag full of throw-up in my room. 

No clue how it got there. There are pictures of her and me hanging in my front yard.... I don't know who took them. I haven't talked to her since that night, and our mutual friend hates me now because of this. It's been two years since my favorite birthday took place.


32. Dependent Guy

The most boring older man in the world suggested we go to an incredibly upscale restaurant. Take note, that was on our first date. He said this knowing full well that I was a student and I couldn't afford to shuck out half my rent for a plate of raw beef.

Onto the date itself, he was as funny as cancer. He depended on me to make up 150% of the conversation (he made me order for him, too; Idk why).

When the bill eventually came, it was about $250, and he looked at me expectantly. GURL WHAT??? We (I) awkwardly suggested that he pay (as I almost had no money; I had enough for a taxi back and a burrito).  

So he took it upon himself to start feeling up my legs under the table, seeing as he was generous enough to pay for a meal wherein he ate almost twice as much I did. He seemed disappointed when I declined a repeat performance.


33. Too Populated

This was the summer after high school, and I was going to go to a movie with a girl I vaguely knew from high school. Texted her and asked her if she wanted to grab a bite to eat beforehand, trying to be the nice guy. She says no, she already ate.

So I'm on my way to the theater, and she sends me a text saying that she has a friend or two with her, and I can invite a friend of my own if I want. At this point, I was already feeling a bit awkward, as one of my friends had told me that she was really weird and kinda stupid.

So I call up one of my buddies (said friend), tell him that this chick I'm going to the movies with has a couple of friends, and pick him up.

We show up at the movie theater, and her "one or two friends" are quite literally five or six friends. Oh yeah, and they're all around 15-16, so this just took a dramatically different turn for my buddy, who wants to leave.

Go to buy tickets... oh yeah, she had completely messed up the time by about an hour, so we have another two hours until the next showing. I recommend seeing another movie or going to a nearby restaurant to pass the time... nope.

She wants to hang out in front of the movie theater with her 15-year-old friends. My buddy wants to leave, so I volunteer to drop him off at home and come back.

I take my sweet time getting back and get back just in time for the movie (by no real accident, I tell you). Go into the movie theater, and who's already sitting in the movie theater in the row in front of this chick and her friends?

My sister and her stupid (white) best friend, who loudly calls me "Silly Mike" in a busy movie theater, sit through one of the worst movies I've seen in theaters (that movie "Mirrors" that came out in 2008).

After the movie, the chick invites me back to hang out with her friends at a nearby house, but I use the "I have to work early in the morning" excuse and GTFO.

She texts me nonstop over the next month or so, and I don't respond to any. I couldn't have a single conversation with her the entire time because I honestly believed that she was the dumbest high school graduate I had ever met. Never been happier to delete a phone number from my phone in my life.


34. Too Puzzled

​​So, I had gone on 2 dates with this girl I met through an online dating app. At first, she checked out ok. It was really funny and engaging, and we got along pretty well.

The initial awkwardness had faded, and some of our conversations had trended toward my affinity for cooking. So, we set up a date where I'd cook for her, and she'd bring the dessert.

I had the entire thing set up in a non-intimidating way. It's not mood lighting, but nothing too bright or dark. No sexytime music playing, just some good acoustic tunes with a mix of geeky music scores (we both were comic nerds who adored genre films), some good wine, and a healthy, filling dish.

We were talking, laughing, flirting. Everything was going great. Until she went silent all of a sudden while I was pouring her some wine and looked at me with the saddest eyes ever.

All she said was, "I don't deserve this. You're too good for me. THIS is too good for me." She started crying, and hell, I'm terrible around crying women, so I had no idea what to do.

I just sat next to her and tried to figure out what was happening, saying, "It's ok," repeatedly and looking around as if I was going to find something to calm her down absent-mindedly.

She then took her plate, stood up, emptied it in the sink while bawling, and said, "This is too good for me. NO MORE!" before running out.

That was a couple of years ago. Never heard from her again. I still have no idea wtf happened. So, it's not terrible, but it's altogether confusing and weird.


35. Dirty Tricks

The first date with the guy was totally normal and nice. On the second date, he makes fun of my sister for being handicapped and then orders a water cup only to get soda at the fountain.

Of course, the first thing pissed me off, and his faked apology wasn't convincing, but the second thing just proved that he was a self-centered jerkwad.  

I don't like someone who steals, even if it's that insignificant. His true colors came out at the perfect time: early. I was somehow lucky.


36. Embarrassing Times

I was a young man and had recently moved out to a city a fair distance from my hometown. While in town one day, I bumped into an old friend from school.

She was the year above me, very popular, and the one who the guys all had a thing for. Neither of us knew the other lived here. We chatted for a bit and exchanged numbers.

After a few days/weeks (can't remember) of texts back and forth, she asks me if I fancy going out for a drink. Wanting to impress, I decided to pick up some fancy new clothes for the date.

For whatever reason, I don't get around to doing this in advance, so I make a desperate dash around a few shops on my lunch break on the day of the date. At the end of my working day, I quickly slipped into my new outfit and went to the bar where we'd arranged to meet.

She turned up, and we started chatting. Early in the conversation, she says, "You look nice. New clothes?" "These?" I reply. "No, had them for ages." Trying to play it cool.

The night continues. She's regularly looking at me, smiling and giggling. I'm sure that my witty conversation is working wonders.

It's late now, and she tells me she needs to get home. Being the gentleman I am, I offer to walk her to the bus stop. As we stand on the platform, she's still grinning and chuckling away.

The bus pulls up. "One thing before I go," she says as she leans towards me. I closed my eyes, believing I was about to receive a farewell kiss.

I feel a pull around the back of my collar. "Remember to take the tags off your new clothes before you go on a date." She tugs sharply, and not one but two clothes tags come away in her hand. She jumps on the bus and pulls away, waving goodbye and laughing hysterically.


37. Tons Of Inconveniences

On my first date, I picked up the girl and was late to the ferry, making her run for a good 5 minutes in a nice dress and high heels to the ferry to get to the city.

We awkwardly talked for 30 minutes and finally got to the bar that was supposed to have a live band playing. I found out that the band had canceled.

So I figured I'd at least buy us a drink and a nice dinner (since I had got paid that day), but then I found out I had lost my debit card on the way to the ferry.

I somehow recovered and think the dates are going well. I drop her off, and just as she's about to leave my car, we go to kiss - I miss and hit her cheek and exclaim, "I'm sorry." She asks if I want to come in, and I quickly say no. But she's my girlfriend now. So, I did something right.


38. Unexpected Event

I had been dating this girl for about three months at the time. She liked to style herself as cultured and artsy, so we ended up going to this tiny theatre in an old brick building down the street from her apartment for an interpretive dance performance.

Naked dudes ran backward for half an hour with LED light strips roped around them to the sound of weird, metallic, screechy music that was like industrial meets Skrillex in sheer discord and cacophony.

And then that was all cleared away after about 30 minutes, and two guys in skin-tone, skin-tight bodysuits were pretending they were robots to more weird music that sounded like dishwashers full of silverware being rolled downhill.

And that was only the first act. I don't recall much of the second act except naked women keening while striking odd poses.

Afterward, we're sitting in her apartment at the kitchen table, a bit shell-shocked. Even she, a veteran and professed patron of interpretive dance was a bit out of sorts over the performance.

We both agreed that it experience, one that we wouldn't be repeating again. After that, every date I've been on since has seemed quite tame.


39. Annoyingly Clumsy

An ex took me out to see the first Robert Downey Jr. Sherlock Holmes movie on the premiere date- the place was packed, but we were there early enough to have perfect seats.

Anyway, the previews started, and he asked if I wanted anything; I replied that a Coke and popcorn to share would be great. So he gets up to get it.

Ten minutes later...

The movie’s starting, and I'm starting to think, "Where the fudge is he?" I see him come in at the bottom of the theatre, pause to find me, and then start up the stairs holding two GIANT drinks (one in each hand) with a massive popcorn in between them.

He gets to our row and starts shuffling down to me. Well, there was this fellow... Poor guy must have broken his foot because he was sitting in a cast. The ex didn't see the cast and managed to trip (and he was only three seats away from me - so close, yet so far...).

First to come my way is the large cokes. The lid flies off, and I am drenched- literally drenched- in pop. Then, I see it... Tumbling through the air... The popcorn!

My seat and the ex's were tarred and feathered with coke and popcorn. I cleaned myself up in the washroom (I had now missed the first 20 minutes of the movie) and came back only to find MY seat (the dry seat, seeing as my body shielded it from the onslaught of food) occupied by my ex.

He told me I should sit in the sopping wet seat because "I was already disgusting, and he didn't want to get his jeans dirty." I am ashamed to say I sat down… And that, THAT was the worst date I've been on.


40. Huge Regret

I was talking to a girl who looked incredible online, and the chemistry (at that point) was great, too. We decided to meet up a few months later at Leicester Square.

Honestly, I thought this girl sounded too good to be true and that I was about to be catfished. I lit up a few smokes, waiting anxiously, and she turned up, in fact, a lot more attractive than online, and I was surprised.

She said hey and reached for a hug, and I impulsively went for a kiss (don't ask). She turned her cheek. Anyway, I had no idea what to do for the date, so we just ended up simply walking around London.

Actually, we were lost. We ended up in places like Denmark Street, Brick Lane, the National Art Gallery, and such. We were talking and laughing all throughout and such.

At the end of the date, I went to leave her at Victoria station, we rushed, and she missed her train. We sat down in McDonald's for a good hour or so, talking and stuff, and then she left. I got a hug, and that was goodbye.

On my way home, I thought to myself that she must have been disappointed with me (I felt out of her league as she was ridiculously good-looking and had an incredible personality).

Additionally, she must have hated the date as we technically did nothing. Thinking that was the worst date ever (because of my insecurity), I deleted her phone number and Facebook.

She later revealed she missed her train on purpose for me and texted that she regrets not kissing me before she left. We later went on to have the best relationship of our lives.


41. Sudden Third Wheel

When I was a lonely, socially awkward 16-year-old, I put an ad up on a personal site looking for a date. Some girl my age messaged me, and she seemed pretty cool.

So we friended each other on Facebook and decided to meet up at the mall, grab a bite, and shop around. This was my first actual date since the 7th grade, so I was incredibly nervous but kept it together.

We met up and walked around and talked for a bit, and then her friend showed up, and they essentially went shopping and had a girl's day out with this awkward stranger in tow.  

When the date ended, I got a handshake goodbye. A week later, she announced to Facebook that she was in a relationship with her stepbrother. It all worked out for the best, I guess.


42. Strange Setup

A friend set me up with a girl, and it went great. At the end of the night, when I got home, I called him up to thank him for doing that.

  He told me I couldn't see her anymore because she was his girlfriend. They had started going out about two weeks before, and he didn't tell me.  

Then he handed the phone over to her so she could apologize. Apparently, he was waiting in her house when I dropped her off.


43. Shocked To The Bones

I went on a date with this guy when I was 16, and we went to the movies to see xXx (Vin Diesel film) - totally romantic, right? It was pretty quiet, and only two other people were in the screening, sitting at the front.

  Well, I wasn't quite feeling the date but was enjoying the action movie until the guy I was with stood up, strode me, and leaned in for a kiss.

I was totally flustered, pushed him off, and sat watching the movie, totally uncomfortable for the next hour or so. I still cringe thinking about it a decade later.


44. Thirsty One

My most recent one: I took a girl to Art Walk (A bunch of art galleries downtown have feature artists, wine tastings, street vendors, etc.).

The first place we go, she has a whiskey. In the second place we went, she had a whiskey sour and two double Manhattans because the first drink wasn't strong enough.

The last place we go, she has three Jack Single Barrels and NINE Jamesons. All of this is on my tab, by the way. While drinking her Jameson, she punched me in the face for telling me to slow down on the 5th one.

I had to carry her back to the car, and once she got in, she passed out. Five minutes later, she pees herself. I got her back to her dorm.

Somehow, she left her keys at one of the bars, so I had to go back and get them. Get back to the dorm. Campus security is there taking care of her.

Now I have to answer a bunch of questions because they think I slipped her something. Finally, convinced them that she did this to herself, got released, and headed home. All of this happened before 10 o'clock.


45. Got Tricked

When I was 16, I was friends with a girl who was a year younger than me. She called me one Saturday and asked me if I wanted to go to the mall with her, so I agreed.

However, her older brother shows up to pick me up. He said we were picking my friend up, so there was no big deal. But we go straight to the mall. I ended up walking the mall with her brother for hours, trying to figure the whole scenario out. No mention of the sister at all.

This was before cell phones were big, so I had to find a pay phone to call my parents and ask them to pick me up. The guy was nice enough, but really?

Tricking me into a date is not how to win me over! My parents mentioned it to their parents, and they admitted it was a whole setup. Yeah, I wasn't friends with that girl after that!