Raise your hand if you think dating is fun. I can’t actually see any of you, of course, but I’m going to go ahead and assume there no hands in the air right now. Dating is generally thought of a necessary evil, the sort of thing you hope turns out well but might be awful. The only upside to the awful is that it can result in a lot of great stories.

Twitter user @millercycle posed the following prompt to the internet at large:


There were hundreds of replies, and most of them were fascinating, cringy gold. Enjoy this selection of examples.

14. Moving on

Please don’t use a date as a therapy session.

13. Prison and a movie

This is the grossest show and tell I’ve ever heard of.

12. Insult to injury

This is called “negging” and it’s a pickup artist technique employed by douchebags. Never be this guy.

11. A taxing experience

I have so many followup questions for this one.

10. Extortion

Boy oh boy can money make people terrible.

9. Candid camera

Look, no kink-shaming but you need CONSENT from EVERYBODY.

8. The young and the restless

This is…concerning.

7. Literally Hitler

How is this even possible?

6. Drugs not hugs

Everybody knows you don’t do this ’till the third date.

5. B I T E

I really REALLY need to hear your worst story now.

4. Nec-romance

Weirdest. 3 way. Ever.

3. Distance

Welp. She’s a free spirit, we can give her that.

2. Stranded

As someone who recently visited Detroit, this is a fate worse than death.

1. Pickpocket

Welp. Run, I guess?

These stories are truly helping me feel better about the fact that I haven’t had a date in a while. I think I’ll just revisit them every time I need that boost. Thanks for validating my loneliness yet again, internet!

What was your worst date?

Tell us in the comments.