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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90points
#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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70points
#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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61points
#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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60points
#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."
"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?"
"Jesus... you dodged a bullet! What a psycho. Who puts their shoes on the table?"
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59points
#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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54points
#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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48points
#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."
"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."
"Least I have chicken."
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46points
#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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43points
#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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42points
#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.
"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."
"I hope she sat there and reflected on this for a while... Probably didn't but one can hope."
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42points
#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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41points
#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.
"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."
"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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39points
#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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38points
#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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37points
#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.
"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."
"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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37points
#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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36points
#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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35points
#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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35points
#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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35points


