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People Share Truly Horrific Stories Of Their Worst First Dates

MonicaJuly 26, 2022

A Clockwork Orange

When a date is going well, it’s hard to know when to say goodnight. After this Reddit user had one of those wonderful first dates that make us believe in love, it went south. His date asked him if he’d ever seen A Clockwork Orange, to which he said he hadn’t. 


Without hesitation, the girl suggested they watch the movie. After watching the gruesome movie, the girl was in the mood for some “sloppy toppy.” He was not. His mind was full of horrible images. Maybe she’s into BDSM and felt turned on after watching the movie. That’s a person to reconsider (via Reddit).


Bring The Mother

When you go on a date, you don’t expect them to bring their mother. That’s something that happens months into the relationship after you’ve set a solid foundation and like each other. For some reason, this person thought it was a good idea to bring their mother along on one of their very first dates. 


It could’ve been a cute evening, but this person thought it was incredibly awkward. We’re not sure we’d want our parents on any of our first dates, or any of our dates, ever, but this person did it without hesitation. At least he knows she and her mother have a good relationship (via Reddit).

Natural World Today

Pre-Cellphone Era

Todd mistakenly didn’t ask his first date for the correct address. If this happened nowadays, it wouldn’t matter since something like that could be fixed with a quick phone call. Unfortunately, this happened before cell phones were a thing, so Todd had to go the difficult route and ask a friendly neighbor to help him find his date.


He must’ve gone to the wrong house because the elderly couple made him watch TGIF while they searched for a phone book. That’s one way to kill some time while you wait. It’s a funny story to tell on one of your first dates, though. Let’s hope she was understanding and found the whole thing hilarious (via Nature World Today).

Natural World Today

He Gave Up 

Parallel parking is stressful. If you have a bad temper, it can make it even worse. This guy was a big jerk and left his date stranded on the side of the road after he couldn’t parallel park. Instead of trying to find another parking spot, he drove off and left her there. Maybe he was so embarrassed that he didn’t want to face it. 


Because of this, she had to walk home alone. That’s not a great way to spend one of your first dates with someone. As we’ve said many times before, it’s better to happen on the first date instead of months into the relationship (via Nature World Today).

Natural World Today

Catch Me If You Can 

There are some people out there who leave impressions, and others who don’t. This guy certainly didn’t leave an impression on this woman, since she forgot what he looked like. After she walked around the entire restaurant looking for him, he finally flagged her down. 


The best part is that he allowed her to walk around and look for him. He sat there, thoroughly amused, as she wandered around the restaurant, lost and confused. Even though that’s harsh, it’s quite a hilarious way to start the first date. At least it ended in a beautiful romance, and the two of them ended up getting married (via Nature World Today).