50 Funny Bad Date Stories

1. “First date. He worked at a flight school about thirty minutes away and wanted to show me around. As we drove near the runway, we noticed these huge letters sitting on it. They said, ‘Will You Marry Me?’ – somebody was proposing to their girlfriend. We watched the proposal unfold for a bit, and I said, ‘you should take notes; that’s a great way to propose to someone as a pilot.’ He looked me right in the eyes and said, ‘That’ll be us someday.'”

2. “It was a double date that he and his roommate planned. We went ice blocking- where you get a big block of ice and use it to slide down a hill. My date was infatuated with his roommate’s date, and he did not seem to remember that I was even there. At one point, the other couple was like, ‘We should go down the hill in pairs! We’ll go first.’ So I sat on my ice block and waited for him to join me. He didn’t. I said, ‘Do you want to go down together?’ He said, ‘Nah, you go.’ That was all he said to me for the whole night.”

3. “He showed up 45 minutes late to brunch and only talked about his truck. Then he invited me to his apartment, so I figured I would give him another chance. He was very excited to show me his new La-Z-Boy recliner, which I sat in. I said, ‘This is a nice chair; I like it!’ He pets my hair and said, ‘Oh, I bet you do.'”

4. “When we were eighteen, my friend met a guy through Snapchat that she wanted to go out with, so we planned a double date. We were all going to meet at Chick-Fil-A for dinner and then play games at her house afterward. He arrived to pick her up with two fourteen-year-olds. He wasn’t babysitting them, he wasn’t related to them, and he didn’t find them hitchhiking – they were his friends. So me, my date, my friend, Snapchat guy, and two fourteen-year-olds ate some Chick-Fil-A until my friend faked a family emergency, and we left.”

5. “He wanted to go for a ‘sunset hike,’ and he gave me a location to meet him. The hike was ridiculously steep and four miles long. There was a point where you had to hold on to a rope to pull yourself up. As we climbed, the sun went down. When we finally reached the top, we admired the view for a while, then started our journey back down. Going down was way scarier than going up, especially because it was dark. I used the rope for a while, but the rope eventually ended, and I was on my own. Rather than fall to my death, I butt-scooted my way back down, which caused a rip in my leggings and pride.”

6. “I met him at a school event, and he invited me to make burgers. When I got there, he decided that, instead of making burgers the normal way, we would throw all the ingredients (raw meat, bun, lettuce, onions, ketchup, pickles) in some tinfoil together and cook it in the oven. While they cooked, he serenaded me on his didgeridoo (no lie). We cooked the ‘burgers’ for an hour but, as you can expect, they never quite cooked properly. I tried to pick out the edible parts and eat them.”

7. “A girl reached out to me for a date. When she came to the date, she showed up, waved at me, left, then called me. She had put me in her phone as someone else and scheduled the date with me thinking I was that other person.”

8. “I was volunteering at a Master studies orientation market when we met. The cute girl had a nice chat and set up a date. I think I was 22 or 23 at this time. When the day comes, I pick her up at her place. It turns out she lives with her mom, and they have a rather childish argument about whether or not her bicycle lights are working but alright. Moms will be moms. We have dinner and talk about this and that. She tells me about her horse, I tell her about when I tried horseback riding as a kid, and we laughed. She talks about an actor who is so cute. So instead of taking a walk downtown after dinner, we decide to see the latest movie with that actor because, why not, it’s chilly anyway.

During the intermission, we talk about music, and she hasn’t heard of any of the bands I listen to, which is odd because they’re all evergreen pop and rock acts. I ask her about the music she likes, and she mentions many current boy bands. I’m starting to have a horrible hunch and ask her a few more questions before I finally give in to that sinking feeling and ask her the question… ‘How old are you?’ It turns out she’s fourteen… and a half. The guy behind us just about chokes on his popcorn as he realizes what’s happening. It turns out she wasn’t at the orientation market to find a master study; she was tagging along with her older sister, who I never met or heard about.”

9. “I went on a tinder date; the person I matched with was quite nice. However, she bought her ‘friend’ along as a sort of security gesture, who happens to be the human embodiment of a wombat. This wasn’t too bad as she initially just went to the bar area whilst we had a quick dinner. This lasted about 20 minutes until she returned and kept drunkenly making jokes about how she was ‘So unlucky I didn’t match with her on tinder.’ I ended the date within about 10 minutes and went home, I got a text saying ‘I am so sorry’ from the tinderella and she offered a second date with no friend. We dated for a few months, and then about a year later, I got a Facebook message from the wombat. ‘You’ll never guess what I named my child.’ It was my name, with the wrong spelling.”

10. “Definitely one of my worst has to be a Tinder date with a guy who looked and sounded like he was normal (enough) to warrant meeting him IRL. After a fairly expensive dinner, he gets offended when I don’t pay the full bill (I’m a student, and he’s a banker) but finally agrees to split the bill.

I stupidly agreed to go for a few drinks as it was still fairly early. Where he proceeded to tell me his problems with his ex, how he doesn’t like independent girls ‘They should be waiting at home for you to cuddle, not doing their own thing!’, and that he likes his girl’s chunky (after I was talking to him about some good runs in the area we live in, I’m also fairly slim) and that he couldn’t deal with someone who didn’t understand that his career was his only priority in life. At that point, I excused myself and said I had an early start the next day, so I had to leave. On my walk home, I receive a message from him saying, ‘Wish I’d gotten a goodbye kiss; you looked good enough to eat. Gobble gobble.’ Never replied.”

11. “We had dinner, went to my place, and watched movies. He left around 2 am. Half an hour later, I got a call for me to come to bail him out of jail because he didn’t know his license was suspended. Awesome.”

12. “The plan was to have dinner and play games at my house. On his way over, he called and asked if he could bring his son. I didn’t know he had a son, but I didn’t have a choice at this point as he was already driving. Upon arrival, he introduced me to his ‘son’: a stuffed Baby Yoda doll. He holds, talks to, and feeds it dinner. I attempted to speed the date up, finally, at 9 p.m. I say I need to head to bed as I have an early morning. He hugs me, goes in for a kiss, and then bites my chin.”

13. “He told me that my playing with my hair indicated that I was insecure. I looked him right in the eyes & said, ‘Or maybe it just indicates that I’m bored.'”

14. “I’m in my mid/late-20s. A mutual friend introduced us, and the first date was dinner. On the second date, she says she’ll pick me up, and we’ll go for dinner. Her car pulls up. Her 60-ish-year-old parents are in it as well. Surprise! She thought I’d like to meet them.”

15. “Everything that could go wrong went wrong. He took me to an aquarium on the other side of the city, but the tanks were dirty, and it was just an overall awful aquarium. Then he wanted to be romantic and took me to the river that ran through the city, except it was cold and rainy. We ended up sitting in a tunnel, shivering to wait for an hour for the next bus. Then he couldn’t remember the way home, and we got lost on the bus system for another hour before finding the subway and making it home. To top it off, the dinner we ate gave me food poisoning. Bless his heart, he tried so hard, but it was just awful.”

16. “Guy kept talking. Constantly. You never asked about me. I couldn’t get a word in. Although I knew he was a bit of a talker, I thought it might be different while on a date. NOPE.”

17. “I’m Australian. My profile said I was Australian. Firstly, my date says, ‘I hate Australians.’ Didn’t last long, lol.”

18. “Have you ever played frisbee golf when you hate frisbee golf? It’s like playing fetch with yourself, only it ends up in bushes and trees, and you lose the dang thing every time. I made it to the third hole and pretended to take an interest in some ducks. Still ended up marrying him.”

19. “It was with a guy who had recently been broken up with. We were already friends, so we went to his house to watch a movie/play video games. Right off the bat, he lays on the couch and goes on his phone; I have nowhere to sit and end up on the floor. He then opens his exes Facebook page and proceeds to show me pictures of her. When he was done doing that, he fell asleep. I didn’t have a car then, so I called a ride and played his Xbox while waiting.”

20. “She told me the only reason she was dating was to find someone to pay her rent and pay for her kids, and she even asked if I was up to the challenge. It didn’t work out for her.”

21. “A guy took me home to meet his mother on our first date. I thought we were going for coffee. We did… At his mother’s. When I walked in, his dog greeted us enthusiastically and peed on my shoes.”

22. “He took me to Olive Garden and peed in the parking lot.”

23. “Friend of mine that I have feelings for comes over to say goodbye before she leaves for a few months. I get her to hang out before she goes, and we watch a movie. I proceeded to get closer until we kissed, I finish confessing my feelings to her, and as she responded, I ran outside and started puking. She starts rubbing my back as I empty my stomach. Super embarrassing.”

24. “She picked a fight with a construction worker on our train ride home and then pushed me into the guy to defend herself.”

25. “I’m trying to get some semblance of a conversation going while she’s just sitting there flipping through her phone and giving yes-no answers to any question with zero effort to having a conversation. Eventually, I stopped trying, and after about 5 seconds of silence, the girl looked up and went, ‘why are you staring at me? I’m leaving.'”

26. “Went on a blind date with a lady who wouldn’t stop picking at her scabs. I just made a pile out of them on the restaurant table. I excused myself to use the washroom, and when I returned, my soup was there, but the pile of scabs wasn’t. No, I didn’t eat the soup.”

27. “We spent most of the date shopping for clothes for another date she had later that week.”

28. “Meet a guy from OkCupid. He seems nice but never stops talking. After interrupting me for the 3rd or 4th time, I finally ask him, ‘do you want to hear anything I have to say?’ He apologizes profusely, says, ‘you’re right, I’m so sorry!’ and pulls out a pad of paper and a pen. He then jots notes as I’m telling him about myself and whatnot. I finally ask him what he’s doing, and he says, ‘oh, I’m writing down things I want to tell you when it’s my turn to talk again.'”

29. “Got stood up at a café. She called and told me an emergency had come up ad she wasn’t going to make it. I had only been waiting for 3 or 4 minutes and wasn’t too upset about it, so I called a friend to see what he was doing. I met him across town at the bar he was drinking at, where he introduced me to my date he had just met playing pool there.”

30. “On the way out of the restaurant, he honored me with this fantastic compliment: ‘I just wanted to let you know I had a great time with you. You are officially #2 on my list of girls I’m considering dating. Hopefully, you can rise to #1 by the next date ;)'”

31. “When I was 16, I was into punk rock and being an angsty atheist. Some guy in my religion class asked me if I wanted to go to a local rock show with him. I agreed. The ‘rock show’ was a church youth group with a Christian rock band. I showed up in fishnets, combat boots, and a leather jacket. It was extremely awkward.”

32. “I think the worst date I’ve ever had ended with me having to change the tire on his car. In a dress. At night. While he looked on in amazement at how a jack works.”

33. “He whispered the whole time that I couldn’t hear a single word he said. I kept mentioning that the restaurant was loud (it wasn’t) and asked him to speak up. I was forced to do the smile and nod, which didn’t work very well because he gave me a few weird looks that made it clear I was smile-nodding through a question.”

34. “20 years old…Cold Winter evening…Heading out on a first date to a Christmas Party. All dressed up in a gorgeous dress and high heels. The gentleman that he was, opened the door for me, and as I stepped out onto the stairs… I slipped on ice and fell down the entire flight of stairs.”

35. “It was a minor league hockey game. He brought his brother, and when I went to the bathroom, the game ended, and they forgot about me.”

36. “Told me he wasn’t wearing any deodorant, but we were eating a ‘hippy’ restaurant, and no one else was wearing any either. The entire restaurant turns and stares. I wanted to die.”

37. “I went on a blind date where the restaurant caught on fire, and I slammed her foot in the car door, breaking two bones. When your blind date ends at the ER, you are going home alone.”

38. “A guy insisted we go to the drive-in movies. Told me to get in the trunk because he ‘only brought enough money for one ticket.'”

39. “I went on a first date where the dude took my phone and wouldn’t give it back and then bit me when I tried to take it. Left a bruise for a few weeks.”

40. “I was at the cinema with her, and we were watching the notebook. The movie started to get very intimate, and I could see in the corner of my eye that she wanted to kiss me. I turned around to see her with her eyes closed moving towards me with her lips ‘ready.’ I was very nervous because I had never been kissed before, so I made an excuse to ‘go to the bathroom.’ I didn’t even go; I just ran home.”

41. “Was at a movie with her. I was told she was a shy friend. In the whole movie, we don’t talk. I receive a text from her saying, ‘well, this is awkward.’ She was sitting right next to me….”

42. “Took a girl on a lunch date to a local burger place we ordered, got our food, and then she just left with her food and never said a thing about it.”

43. “It was our first date, and we went out for coffee; he paid. We had a good time and decided to see each other again next week. Two days later, I saw him in the grocery store, and he asked me when I was going to pay him back the $1.50 for the coffee.”

44. “I tried to kiss her but ended up headbutting her.”

45. “I was playing Mario Kart with a guy I was dating. I paused the race to change the dying remote battery. Pausing and unpausing messed the guy up so he came in second instead of first. He started screaming at me that it was all my fault he didn’t win. He wouldn’t talk to me for the rest of the day.”

46. “My dinner date started cutting his fingernails at the table.”

47. “I may have commented on a girl’s nose ring. She had a stud in her right nostril. Turns out it wasn’t a stud. It was a mole, and she was very self-conscious about it. The mole was shiny and looked like a semi-precious stone to me.”

48. “I was with a girl at the movies or something, and she was eating peanuts. She approaches, kisses me, and then pushes chewed-up peanuts from her mouth into mine like a bird feeding her baby birds. I immediately pulled back and told her not to do that. We spent the rest of the time there awkwardly quiet.”

49. “I went out on a date with this girl, and we were strolling through the park, and we were looking at each other all awkwardly in love, and a bird decided this was the best time to make a poop mid-air and it landed right on her nose.”

50. “The guy came to my door, I opened it, he said, ‘I’d give you an eight, but you are wearing pants.’ And then I shut the door again with him on the other side. It was a concise date.”

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