10 Guys Share Their Hilariously Awkward First Date Stories

You know how first dates are always awkward with all the nervousness and weird energy between you and your date. Well, these guys were not lucky either. Here are 10 guys sharing their hilariously awful first dates.

  1. “Back in college, we planned a little “date” with this new girl in my class. We barely knew each other, so I didn’t expect much to happen. That Saturday, we spent the whole afternoon at the beach. It was getting pretty late but she didn’t want to leave. At around 7pm, she went back into the water for another swim. Then suddenly I hear this loud scream. She had been bit by what I suppose was a Jelly fish on her left breast. She told me to suck it to draw the poison out. I have never been so happy in my entire life.” – Tyler, 22
  2. “I met this girl on Facebook a few years back and we really hit it off. So we plan a date one weekend to the see a Star Wars movie. Half way through the movie, she excused herself to go to the bathroom. But as she was standing up, she lets out this really loud fart. Everybody in the nearby seats turns around and stares at us, some giggling under their breaths. I tried to pretend not to notice but the damage was already done. She never came back to finish the movie and we haven’t talked since.” – Dan, 23
  3. “This one time I took this freshman girl to diner at a cafeteria just off campus. I was a senior and so I was pretty confident. We had some interesting conversations throughout the meal and I could tell that she was already into me. Until it was time to leave. I realized I didn’t have my wallet on me. I couldn’t ask her to pay for the food since it was our first date, and hey, she was a freshman. We had to wait for my roommate to leave work and pass by to pay for the meal.” – Chris, 24
  4. “Stay away from Tinder girls! They are too flirty. I matched with this superhot girl on Tinder. Her name was Maya. For our first date, we met at a local bar for a beer and some chicken wings. After 2 bottles, she started checking out this young bartender behind the counter. She became so distracted that I had to excuse myself to go the bathroom. When I came back, she was at the counter flirting with the bartender. It’s the only time I felt offended by a woman being too horny.” – Kevin, 24

See Also: Men Describe Their Creepiest Experiences with Women and it’s Hilarious

  1. “My parents had just bought a new house and our new neighbors seemed pretty excited (They still are to this day, I’m not sure why). Right from the first day, I felt a connection with Kenzie, their daughter. The first time we decided to hang out, it was at my place. My parents were out of town and my big brother was out drinking with his friends or whatever. So she came and we ordered a pizza. It was my first time with a girl in the house without my parents around and so I was nervous. She suggested watching a movie and I rushed to my brother’s room since he had a great collection. We get set up on the couch to watch the movie, press play, and boom! It was a hardcore porno film. We watched the whole thing like two innocent kids. I didn’t even realize how wet I had gotten till she left.” – Jay, 21
  2. “I asked my sister to set me up with one of her friends for a date. She was generous enough to set me up with Carol, the hottest one in their group. What I didn’t know was Carol was going through a nasty break up with her ex. On our first date, she spent the whole time telling me about their relationship. She was so absorbed in her stories that she even described their sex to me. I thought it was straight up rude. It’s the only time I’ve ever thought of faking a phone call to cut short a date.” Aiden, 23
  3. “A girl once sent me a text saying that she had gotten my number from one of her friends because she thought I was cute. We ended up talking and had some really interesting conversations. When we finally agreed to meet for the first time, it was at the college cafeteria. I get there earlier and order myself a cup of coffee. Then 20 minutes later, my best friend Tony shows up with several guys from my class laughing. Apparently, all this time I had been texting Tony and it was just a stupid prank. Screw you Tony!” – Jeff, 25
  4. “I got excited about a girl I had matched with on Tinder. She was really funny and I liked her. She was supposed to come over to my place to see a movie, but my brother dropped by for a sleepover, so we had to change the plan. We met at a McDonald’s restaurant just off town and somehow, we ended up talking about our past relationships. I realized that all her life she had only dated black guys. I was only 24 and her ex-boyfriends were all over 29. The only thing I could think of was how “insufficient” I would be when we finally had sex. I got so uncomfortable and lost interest in pursuing whatever feelings were developing between us.” – Noel, 24
  5. “My boss had just hired a new office assistant and I decided to ask her out first. She agreed. My office is was across the hall from where her desk is so we didn’t really see much of each other at work. Come our date, we met a nearby restaurant for diner. People say I have a crazy sense of humor, and I think she thought so too. When I made my first joke, she made this weird loud giggle. I ignored it the first time. But as I made more jokes to keep the date lively, she kept making these loud disturbing noises and I realized that that was actually how she laughs. Everybody at the restaurant kept staring at us.” – Sid, 26
  6. “I once made a girl laugh so hard she peed on herself. Every time I meet a new girl, I make the same joke. Works like a charm!” – Max, 22

4 thoughts on “10 Guys Share Their Hilariously Awkward First Date Stories”

Leave a Reply

Your email address will not be published. Required fields are marked *