Dating can be a wild ride, full of surprises and, at times, the funniest disasters. While we often hear about the happy endings, it’s the cringe-worthy dating moments that make for the best stories.
We’ve gathered real-life anecdotes from 20 brave souls who shared their most embarrassing date stories and hilarious dating fails. From awkward encounters to misunderstandings, these tales remind us that even the cringiest experiences can lead to laughter. So sit back and get ready to giggle as we dive into the amusing world of dating gone wrong!
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When she got mad at me for wanting to leave when all she did the entire time was mess around on her phone and post selfies of her and her coffee I bought her. Checked her Insta profile later on (she wanted me to follow to boost her) and the caption was something like "treated myself #blessed #sogood #coffee" literally couldn't hold a conversation at all. So self-absorbed.
Wish I had video of that "date" just to laugh at it again. @GassyMagee / Reddit
First date. Guy kept GRABBING my stomach, saying that’s where his baby would be. He was talking about moving into my house, where his stuff would go, that he was going to marry me etc.
I got on a random stopped bus and asked the driver to please just drive 😩😭@TQV94 / X
We met up at a local burger joint, and he didn't say a single word. I asked questions, and he responded with head nods and occasionally a chuckle that's more like a release of air. I was pretty sure he hated me, so, I told him I was just going to go home.
That's when he finally spoke. He asked me why and told me to please stay...so I did, and then he continued to sit in silence. Looking back now, I realize he was just nervous but, man... At the time, I really thought that I must have been horrible to be around.
Update: We've been together for 2 years, and he actually talks to me now. @foogliwoogli / Reddit
Girl and I made plans to meet at an outdoor mall and see a movie, this was back in middle school, so my mom had to drive me in about an hour’s worth of traffic, and she cancels 15 minutes out. I felt so bad for my mom driving me all the way there already, so I simply pretended like she hadn’t canceled, my mom dropped me off, and I watched a movie by myself. Almost cried, but I kept it together.
But I mean the movie was good at least. @Unknown author / Reddit
This was embarrassing in the moment, but it worked out.
It was a 2nd date, but it was also Valentine's Day, so I decided to get her flowers, a card that plays music, and some chocolates. It was freezing cold, but I didn't have anywhere to keep them besides my car. I took the chance the flowers might die.
We had a nice date, and when we get back to my car, I got them out. Oh, those flowers were DEAD. "Ah well...". She opened the card, and the sound chip just went bbbzzzzzzzz. I sighed and said, "Well... I hope the chocolates are okay". She started laughing and gave me our first kiss. @Unknown author / Reddit
We’d love to hear about your own hilarious or disastrous dates — share your stories in the comments below!
And don’t miss out on more captivating dating tales! Click to check out 20+ Waiters talk About the Most Awkward Dates They Witnessed Firsthand.
