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It’s a silently and universally acknowledged truth that dating is hard. Every person who has dabbled in the dating game has at least one bad first date story to tell, and it’s always a treat to hear about the misadventures of others. Not because we’re mean or anything! It’s just… oddly entertaining. 

When it comes to the worst dates ever, men have had their fair share of disastrous experiences. From a pickup line that missed the mark to a complete lack of chemistry or the feared awkward silence. Sometimes, things start out great and take a sudden turn for the worst. Other times, the disaster is clear from the get-go. But no matter how they play out, some of the worst first date stories go so perfectly wrong that they become legendary, like amazing tales told over drinks at bars and remembered for years to come.

That’s why we were so excited to find this Reddit thread packed with the craziest dating stories guys have, and we’re sure you’ll agree that some of these people really dodged a bullet! Here, we’ve rounded up the (best?) worst date stories we read, shared by men who had the guts to tell and relive all of the awkwardness, discomfort, and horrible conversations they had on their bad date.

#1

"I wanna preface this by saying I was young, dumb, and didn’t have a car. (This was in high school).

I waited like 5 hours for a date once they never showed up. We were in two separate small towns so we decided to meet at a local city’s shopping mall. I was super excited cause I had this whole cute date idea planned and I really thought I liked this girl - again, I was dumb.

Had my sister drop me off at the mall pretty early then agreed upon, and texted her to let her know I was there. No response, no worries. Sat down and just waited. After I realized she was a no-show and after she texted me claiming her phone died and whatever, I just got up and did the date by myself. I didn’t wanna call my sister to come to pick me up because 1. I was embarrassed and 2. She had a whole day of stuff she had to do so I was stuck there until the agreed-upon time.

Took me out to a nice meal, saw a movie, got some ice cream, and walked around a nice little park."

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#2

"An internet date and I were having a great conversation. I mentioned I was in the Army for 7+ years, and she thanked me for my service and said: "every girl knows: if you want a smart guy, you date Navy or Air Force. If you want a really great-looking guy who maybe isn't the sharpest needle in the sewing drawer, you date a Marine."

Me: "What about the Army?"

Jane: "That's the one you're married to while you're sleeping with the other three.""

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#3

"A girl that I met on Tinder suggested that we go to a particular restaurant to have dinner. No big deal, sounds good. So we get our food (fast casual sort of place) and she’s really insistent that we eat at a particular table that’s sort of far away from the actual restaurant. Dinner goes fine, I guess. I don’t really like her that much and she seems like sort of a mean person, but I just commit to finishing the date and not going on another one.

Later that night, she starts getting a bunch of texts and acting distracted, and she tells me that it’s her ex and that he saw us on the date. Turns out that she intentionally sat us in front of the tattoo place where he worked at so that he would see us and be jealous.

It sounds like one of those things that happen in a sh*tty TV show, but it happened to me in real life."

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#4

"Matched on tinder and she seemed completely normal. After talking for a few days and thinking I knew what kind of person she was I met her at a Mexican restaurant (her choice). She showed up with a giant Dirty Harry-style pistol on her hip. When I asked her why she said she didn’t trust brown people. I left black marks pulling out of the parking lot."

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#5

Hardly_at_Work said:
"It was at a coffee shop in a library. She showed up and the very first thing she did was remove her shoes and put them on the table. Later she mentioned how she was obsessed with victims of serial killers and had them tattooed on her body."

peace_love_empathy replied:
"Jesus... you dodged a bullet! What a psycho. Who puts their shoes on the table?"

Hardly_at_Work Report

#6

"Showed up on a date:

The first question she asks is: “oh, how did you get here?” Me: “I rode my bike” Her: “ugh I hate cyclists, whenever I see them I want to run them over in my car”

...2 mins later

Her: “so where are you from?” Me: “I grew up in Canada” Her:” I’ve been to Montreal” Me: “oh cool, me too, I really like it, what did you think? Her: “I hated it, I thought it was dirty and the French people are really rude”

...2 mins later, talking about work

Me: “I was in consulting” Her: “ugh me too, I hated it. I didn’t like a single consultant I met”

We left after 30 mins and never talked to each other again."

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#7

"Went on three dates, had nice dinner met her mom and all that, during the third date she got a call in the middle of dinner, finished the call, and said “sorry that’s my boyfriend this is the only time he gets to call from basic” and then she couldn’t wrap her head around why I thought that was messed up. Her reasoning was he was in another state so she can do whatever she wants."

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#8

BootyGrocery said:
"Took a girl to Nandos for dinner, and she ended up talking to a guy she used to date for like half an hour while I sat there and silently devoured my half chicken."

IWantToBeTheBoshy replied:
"Least I have chicken."

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#9

"I met this woman through a dating app and we decided to meet up for drinks as a first date. The conversation was great, we seemed to have lots in common, she was funny, cute, etc etc. Towards the end of the date she tried to sell me life insurance and pulled out some brochures for me to look at."

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#10

"Quick and easy reply. 18 y/o me (21 Years ago) goes on a date to the pub with a crush from school. (UK)

An hour into the date she asks to borrow £20 (edit: which I did give her), and 15 minutes later she's leaving with another guy."

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#11

MurdaVyse said:
"I once met up with an online date and went to red lobster. Pretty girl, pretty decent convo leading up to our meet-up, so I was pretty hopeful. After about 5 minutes in she pulls out her phone. Which is of course normally fine, however, she remained glued to it for the next 20 min. I tried to continue the conversation but her responses became more and more limited.

Eventually, I got a bit fed up and excused myself from the restroom. Caught the waitress on my way and paid for my portion of the meal, and left without another word.

It took her 20 minutes to text me and ask where I went. I told her I didn't want to interrupt the date with her phone."

TheDemonBunny replied:
"I hope she sat there and reflected on this for a while... Probably didn't but one can hope."

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#12

"2009 Was seeing a girl for a couple of weeks and took her across the state to see Keith Urban and Taylor Swift. Paid for tickets and paid for everything... we get to “I Wanna Kiss a Girl” in Keith’s set and she says “I wish I found you attractive so I could kiss you.”

So then we had to finish the show and had a 2.5-hour drive back home."

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#13

brthompson06 said:
"I met this girl at a local dive and she seemed rad... Until she had 6 double greyhounds... We were leaving and she could hardly stand, so I asked her how she was getting home. She says she's going to my house, I say no. This argument goes on for a few more minutes before I just say I'll drive her home. Keep in mind I had told her I needed to be home at 12 am because I worked the next day and it's already 1 am.

As I'm driving she's all over me and getting upset I'm not reciprocating while driving. Finally, get to the address she gave me and it was not her place. She gives me a new address, which is also not her place but the middle of downtown. I can't boot this drunk girl out in the sketch area and feel good about it. The third time's a charm and we get to her apartment complex.

She won't get out of the car unless I agree to go upstairs with her. I leaned in for a kiss... Then unbuckled her seat belt, opened her door, and pushed her out. She texted me the next day and said "thanks for not judging me last night lol"

Oh, I judged you."

hardforbooks replied:
"I thought Greyhounds, you meant dogs. I was like wtf, you hate 6 dogs. I see now it's a drink."

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#14

"We went to one of those frozen yogurt places where you can put whatever toppings on it that you want and they weigh it at the end and charge you for how heavy it is.

This girl loads it up hardcore. Tons of frozen yogurt, and tons of toppings. It came out to like 10 bucks just between the 2 of us.

She then took like 3 bites and threw the rest of it away."

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#15

"My date used 2-hour street parking when we went to see Interstellar. We had to leave about 20 minutes before the end of the movie to get to her car in time. I still haven’t seen the end."

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#16

User No 1 said:
"This one girl kept giving me strikes. I'd say or do something and shed go strike one... strike two... like that.

So I said, "well hang on how many strikes do I get?"

She goes "3 like in baseball"

I go "how many do I have now?"

"You're up to 2 so be careful"

"Oh ok"

And I got up and walked away."

Farkenoathm8-E replied:
"I had a girl do the same thing to me back in high school with pretty much the same ending. It’s 30 years later and now I’m wondering if some poor man married her and is still putting up with that strike bs."

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#17

"When I was in college, a girl I knew asked us, her gal friends if we wanted to see a movie together.

Once we arrived at the theater, we saw a very confused guy, who was also a part of our larger friend group, standing next to her. After we got our tickets, she grabbed his hand and said they were sitting together, and I blurted out “Are you guys on a date?” In my defense, I was, and am, an idiot.

After the movie, we were all still confused and unsure how the rest of the night would it should play out. Someone suggested coffee, but the girl grabbed her date’s hand, giggled, and said they were taking off.

The next day I heard she asked if she could see his dorm. When they got to his floor, on his way to his room, she marched into the common area and sat on one of the couches. He followed, sat down next to her, and she got up and sat on another couch opposite him. She then proceeded to spend the next three hours asking him questions about his childhood and family before abruptly standing up and saying she had to go back to her room, she was tired, no don’t walk her back.

The next morning she called up one of her girlfriends and complained he didn’t make any moves on her. “Zero romantic vibes” is how she described it. He called me up and said he spent the entire evening in a state of confusion. I am female and I am also confused about what exactly she wanted or expected to happen."

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#18

"Met up with a girl through a dating app - Organised to meet at her house for a movie, I get there and she has only a 2-person couch she sat on one side and the cat is sleeping on the other side I try and move the cat but the girl said "excuse me what are you doing" so I awkwardly sat on the floor. 30 mins in I said screw this and walked out. Still laugh about it till this day."

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#19

"I went on a date with a girl from a social group from meetup.com She requested to go to a ritzy restaurant for lunch. Then started showing me pictures of guys she wanted to date after me."

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#20

"She got dropped off by an armed man. Not dropped off at the fancy restaurant we were meeting at. No, she was escorted to the actual table I was sitting at.

She would not explain, so a drink and a short meal later, and I bounced."

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#21

Pillowmaster7 said:
"I definitely went ice skating with my crush, and I fell and broke both my tibia and my fibula and had to have emergency surgery l. Worst date to have with a crush you have liked for about 3 years."

alpacaveloz replied:
"And what happened later? Did you guys have another date?"

Pillowmaster7 replied:
"No, but this happened about a month ago so I'm still healing but I'm planning on asking her again to go ice skating and tell her to finish what we started."

Pillowmaster7 Report

#22

"I had a date with a girl once at Applebee’s (her choice) who, after the date was over, decided to tell me all the things that were wrong with me and my “dating skills”. She took the free meal, but berated me for like 20 minutes."

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#23

"Ooh, I have one. So I went on a date with a girl I worked with. I'm white, she was half Indian. The date itself went really well; dinner, drinks, etc., then it comes to the end of the night and her lift turns up to take her home. It was her mum; not a problem, we were only early 20s at the time. But, it turns out, her mum was massively racist.

To this day, I've no idea what she screamed at me and the girl as she dragged her away and into the car, as it was all in high-pitched Hindi, other than she called me a "white fu*k head" (not the worst thing I've been called).

I asked for an explanation a few days later and it turns out the girl's father was white, and even though they'd divorced over 8 years prior, her mother was still somewhat bitter... we didn't have another date."

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#24

"Matched with a girl on Bumble and we met at a local barcade. She brought her friend group of 5+. It was awkward and we didn't talk much. They invited me back to their house and then they opened up about being a poly group. I politely made my exit and then stopped talking to her when she tried to make future plans. Everyone was incredibly nice, but it was inappropriate for a first date in my opinion."

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#25

"I was on a date with a friend's friend. I didn't know her, only seeing her around from time to time. Never talked to her before. So my friend hooked us up for a date. She looked decent so I went for it. As I picked her up everything went smoothly and fine. Took her to dinner. And as we ate she suddenly started going on about having the sh*ts. She literally did not stop talking about it. Even after she took a 22min toilet break. The thing is I still am a regular at that place and she was the kind of person that couldn't whisper. So the whole one and a half hours we've been there she probably talked about having the sh*ts for 85% of the time (including toilet time, I really don't think she stopped talking in the toilet). I wasn't embarrassed, I felt more like I disrespected this restaurant with me taking her there."

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#26

"We went to a pub near the movie theatre in the city after seeing a flick. I believe it was a girl on a train, a decent movie with a twist. So we get to the pub and it’s typical Boston brews and bar food. You can draw in chalk on the table like you’re a kid. So as she was glued to her phone I decide to draw... then our food arrives and she thinks of an amazing caption for an IG post “hold on this will just take a minute” I return to my fries and drew. She draws something on the table now... it was for another IG post. This girl was literally obsessed with her Ig. She would get up in the morning and instead of answering my good morning text, she’d hop on her IG story and Snapchat posting updates and maybe answer me by 1 pm. Man, that lasted longer, way longer than I’d like to admit. Easiest cleanest break up of my life though."

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#27

CMDR_Brown said:
"I have one, a few years ago I took this girl to see a movie. Things were fine during the movie but once it was over she went to the bathroom and then never came out again. About an hour later her mum turns up and told me she was having a panic attack and I should just go home. Apparently, the lead actor died in another movie and she couldn't cope seeing him in another movie."

damage-fkn-inc replied:
"Has... she not seen movies before this?"

CMDR_Brown replied:
"This was our third date and we had been to see a movie before with no issues, but according to her parents, she hasn't been able to watch a movie with Ansel Elgort in it since a fault in our stars. The funny thing is she's the one who decided we go watch Baby driver."

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#28

"Planned a picnic at a park that was showing an outdoor movie. Wine, snacks, blanket. Was nice. We snuggled a bit. Kissed once. Then when we packed up to leave I held her hand. I was told that was a little too aggressive and forward of me. Then I was ghosted. Super odd."

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#29

"A mutual friend set us up. We had a lot of similar interests and the date was mostly great, but I wasn't that into her after it was all said and done. She wouldn't leave me alone even after I directly told her I didn't want to go on another date. And while it's impolite to kiss and tell, she ended up giving me mono. I'm still salty about it."

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#30

"Had a girl tell me the previous night's dream was her making umbrellas with baby skin while it rained blood, of course, she was hot with this level of crazy but I couldn't leave fast enough... I just remember saying "ok" and luckily at the end of the date."

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#31

Reddit user said:
"She started talking and didn't stop for two hours. I barely got twenty words in. It might have been nerves but wow was is bad."

ajg3199 replied:
"If she spiraled and went on self-centered tangents, that's annoying.

If she did a one-person abbreviated recitation of the Star Wars Original Trilogy, that would have been awesome."

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#32

"A long long time ago, in high school, I was a real nerdy kid but wound up having a date with one of the most beautiful girls in school. We went to an amusement park in Chicago and were having a fairly nice time. We ran into a guy that she knew, and she wound up going on The Tunnel of Love ride with him, leaving me just standing there. Like a jerk, I waited for her and when they were done with the ride he hung around a while then finally went on his way at the end of the night."

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#33

"Pretty much all of them.

One time I hit it off with a girl and was invited to her house after we went to see a movie. The address was different than where I picked her up so I was slightly confused and extremely wary at this point but decided to carry on. Turns out it was her boyfriend's house... He made dinner and was a nice enough guy but it was super awkward. To this day I'm still not sure what her endgame was.

Another time I met this girl on tinder and we decided to meet for a lunch date. She brought 4 of her friends (this was never brought up beforehand) and apparently I was expected to pay for everybody's meal. They all lost their sh*t when I refused to pay and thankfully the waiter was able to pull their tabs from mine after they had apparently told him I would cover everything.

I have a few other horror stories but suffice to say I have since given up on dating."

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#34

"I was basically a girl's uber driver. We had dinner and she had me drop her off across town. She was leaving the next week. She talked about maybe doing long distance. I dropped her off and she gave me a handshake. As I left, I started cracking up from the absurdity of the whole thing."

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#35

"I went out with a girl once that loved to smoke weed. I'm not a big smoker and especially if I'm drinking it makes me sick. So anyway everything was going great we had quite a few drinks and go back to her place. She lights up a joint and I decide to hit it. I spent the next two hours on her bathroom floor hugging the toilet and puking all over. I passed out on her floor that night like an idiot. When I woke up I immediately left and found that she had taken $80 out of my wallet and never spoke to her again"

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#36

n1324 said:
"Went to pick up my girlfriend to celebrate her birthday. I get there and her brother suddenly has to come along with us to make sure we don’t do anything, their mom's orders. I was 19, she was 18, he was 16."

ubcthrowaway2920 replied:
"Would’ve just paid off the brother to go somewhere else for 2 hours and avoid the hoovering lol."

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#37

"Wasn’t bad. After the movie, I let her drive my car a little.

She nearly crashed it into her apartment. Tried to play it off and say “I normally drive like that.” Made no effort to apologize or anything.

Kicked her out of my car and drove straight home."

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#38

"This isn't one date, it's over the course of 4 dates. I only kept going on dates with her to see if she would ever try to pay for something. Not once did she even try? On top of that, she would talk to other guys on our dates and scroll on her phone... Remarkable.

A few days later after our last date, she said she didn't see this going anywhere and I agreed. Sometimes I think about her, never met someone so awful and selfish."

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#39

"Took the very first girl I asked out to the cinema to watch Disney's 'The Love Bug'.

I accidentally got tickets to the wrong film and we ended up watching 'The Incredible Hulk'. She also brought a friend who sat between us.

Never asked a girl out again. Took up programming."

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#40

"I went to dinner and a movie with a girl I had asked out on a whim. Everything went great and we went back to a coffee place to sit and chat for a bit. She was telling a story when her demeanor suddenly changed.

I asked her what was wrong and she simply said "I'm going to head home"

Messaged her trying to figure out what happened and her only response was "You're too much"."

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#41

DerkLucas said:
"Had a date once who kept saying I would be a great dad one day and kept saying my personality would probably be alike a Dutch politician who is nothing like me. All in the first 30 minutes."

slowcanteloupe replied:
"I had a date similar to this. Interestingly she had just been forced to break up with her Dutch boyfriend by her parents. She kept talking about how I would make a great dad by like minute 15 of the date."

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#42

"In HS I got set up on a blind date for homecoming. We had absolutely zero chemistry. We danced one silent, awkward dance out of a sense of obligation. Pretty sure she was as relieved as I was when it was over."

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#43

"I'm a regular at a pub near my house and one Saturday/Sunday just after New year's I popped in quite late on my way home to pick up something I left there. The owner sees me at the door and starts waving me in (a bit frantically but I didn't think much of it) apparently some girl had been at the bar for a first date and got completely catfished, it was awful so she'd spent the rest of the night chatting and drinking with the staff.

The conversation turned to try to set her up with someone and I came up as a candidate, so my turning up was a hilarious coincidence to the guys behind the bar. I get there and get introduced to her but she's pretty drunk and I've just started dry January so my (nonexistent) game is at its worst.

All she can really talk about was how terrible the date was and how it was one of the worst experiences ever. I tried to steer the conversation away and just be friendly but it seemed impossible to salvage that night it could never be a fond memory."

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#44

quick6black said:
"I was recently single and was asked out by a female coworker I was interning with, we went to play pool with some of her friends. Ended up leaving and driving around, stopping at a park with a large pond. Was sitting on a bench watching the water and working up the nerve to kiss her. Turned to look at her, and she looked at me, then she blurted out "what you look like you are going to murder me." That quickly changed my mood so I just drove her home. The internship was over, never talked to her again."

Diablo165 replied:
"AHahahah! That look of concentration/intense thought before my making a move = RBF.

And I'm sure she realized she stuck her foot in her mouth AS SOON as she didn't. The lack of any further interaction must have been a kick in the bits for her."

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#45

"Had a weird date where the date parked at a gas station. There is one a block from the restaurant and one 15 blocks from the restaurant.

We get done and she goes to the gas station one block away and can’t find her car. She thinks it’s stolen or towed so we call the cops.

Cops show up at my place and take statements. Turns out the car was at the gas station 15 blocks from the date spot. Apparently, she couldn’t remember walking nearly a mile to the restaurant and thought it had been a block. The first red flag of many."

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#46

"A girl was super excited to meet with me, we met downtown, and she showed up in an oversized hoodie, checkered pants and beat-up sneakers, and unwashed hair. I didn't think much of it more than it was a bit weird not to dress up for a date. She was super quiet the whole date and it was super awkward. Later she called me up and was suuuuper excited once again to go on a date, and we did. She showed up in an oversized hoodie, checkered pants, beat-up sneakers, and unwashed hair, exactly the same outfit. We had another super awkward date. The third time she showed up in the exact same outfit, was super awkward, said almost nothing the whole date once again, and barely looked at me. After that, I told her that we shouldn't go on another date. (I know I probably come off as shallow in all of this but damn, make an effort please)."

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#47

"Matched with a girl on Tinder. Fairly normal conversation. Decided to meet up at a local brew pub.

She showed up 20 minutes late. She was visibly shaking. She refused to make eye contact. I tried asking leading questions and only got one or two-word answers.

During the middle of an uncomfortable silence about 15 minutes in, I excused myself to go to the bathroom. When I came back, she was like "I'm gonna go..."

"Yeah, you probably should"."

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#48

"Today in fact, because I got stood up. Went to the agreed spot and time and waited for several hours. I messaged my date a few times and still no response. Why I waited? I don't know, took the slowest train home to boot."

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#49

"Not as exciting as a lot of the others in this thread- but we went to a pop-culture event at a museum, and she was just... super quiet and awkward. I constantly tried to make conversation and lighten the mood but she seemed hellbent on resisting.

At one point we were waiting in line for something, and I struck up a conversation with a middle-aged guy in front of us. I had a better time chatting with this random guy than I did my date (who was standing right next to me in silence, I should add)."

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#50

"Halfway through dinner at Denny's (her choice, not mine), on my birthday, she told me she liked the gay guy on the water polo team and left me with the bill."

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#51

"I went to a concert with a girl I had just started seeing. It was Catch-22 opening for Less Than Jake. I wasn't familiar with either band but I do kinda like ska so I would up enjoying Catch-22. Hated the Less Than Jake set, and my date insisted we squeeze through the crowd to the very front. There was a friendly but lively mosh pit going on behind us, and we were quite literally being pushed against the security barricade the whole time. Also, people were constantly crowd surfing and the crowd passed them to the front. Holding up someone who's crowd surfing is easy when you're in the midst of a crowd but if you're upfront like I was then you're doing it by yourself.

90 minutes of being crushed against a fence listening to cr*ppy music and catching crowd surfers and setting them back on the ground were my worst date."

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#52

"She seemed a bit weird, but okay, I asked her out. We went to this gamer bar, and we played some board games, but she seemed weird, for example, she wore her coat inside the bar (it was winter), then she told me about her phobia where she can't be outside in the nighttime. So I was like okay, weird, then I said goodbye, wanted to give her a hug or something, but she just jumped on the first tram, without saying bye and she ghosted me."

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#53

"Took this girl out to a coffee shop and she wouldn’t stop talking about horses for like 4 hours. Then on our way back to campus she wanted a bite to eat so she made me buy her subway but then never ate it! Just saved it for the next day!"

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#54

"I asked her for coffee she said no but she is going out with her friend to play pool at a bar that night. I thought okay cool, a whole new experience for me (as a date, I've been in bars before). I got there and tried to get the convo going. Every time she took her shot she would completely forget what we were talking about. It got very annoying having to repeat myself 10 times and not really getting a response. She also at some stage kept on going off about how her friend had slept with a bunch of guys around the bar. She started smoking as well and just discarding the buds where ever the hell she wanted. I'm not a fan of smoking at all. The whole night was just bad, in the end, I just stood there watching what other people were up to."

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#55

"Went on a semi-date with a friend, who said she had just bought a nice dress and shoes and had no place to wear them. Suggest we go out for a fancy dinner at an upscale restaurant and get all done up. We get some wine, she gets a salad and I go for the lamb. Everything is going well until, due to the revealing nature of her dress, I see she has a Lisa Simpson petting a lamb tattoo and tells me that episode was a reason she became vegetarian..."

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#56

"So far it's where I asked a girl over to my house so I could get to know her more and all she did was brag about how high her IQ was and how her family was full of geniuses, her family lives in the poorest area of my town so I doubt the IQ thing. And she bragged about working 2 jobs in high school and being "not like other girls" To sum it up nothing happened out of that."

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