15 People Reveal Their Hilarious Dating Fails

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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I asked out a friend of a friend. I picked her up, and we went to a restaurant. When we got there, she mumbled something about “being early,” but it didn’t make sense at the time. After about fifteen minutes, she asked when everyone else was arriving and specifically inquired about when a certain male friend of mine would be there.
At that point, I pulled out my phone and showed her the texts between us, stating that this was clearly intended as a date between the two of us. She shrugged and said she thought I was joking. Again, she asked about my other male friend’s arrival. Basically drowning in the awkwardness and again confirming that no one else was coming, I drove her home. © hmfiddlesworth / Reddit

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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

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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

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We met up at a fairly casual seat-yourself restaurant. I arrived slightly early, so I went ahead and sat down. He showed up, and we had a nice chat and a nice lunch. We paid and got up to leave... and his facial expression changed dramatically. I realized what had happened. I hadn’t remembered to give him my usual “How tall are you? I am...” pre-date speech. Once we stood up, he realized how tall I am, and his feelings about the issue were written aaaallllll over his face. © LTOTR / Reddit

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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

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On my first and only date with a guy, we were in a park after a light meal, sitting on the grass and chatting. Suddenly, I felt something poke my ass. I looked around, expecting to see a dog (it felt like a nose), but saw nothing and went back to talking. It poked again. I looked around. Nothing. It poked AGAIN while I was looking and seeing nothing, and now I was freaking out. I stood up, and beneath where I had been sitting, a tiny little mole popped his nose out of the ground and went on exploring in the grass. We had a good laugh and watched him wander, dig, and explore. The mole occupied us for at least 30 minutes before he burrowed under again for good. © DelightfulAbsurdity / Reddit

We’ve all experienced less-than-perfect dates, but some people have stories that really stand out. From strange conversations to downright bizarre behavior, these dates took such unexpected turns that those involved had no choice but to cut them short.