So, what was the worst sex you've ever had? And I feel like this category could probably include more details than just a date.
Ours was probably our wedding night. Crappy motel room (don't ask...) a baby next door screaming and kicking the wall our headboard shared, a mattress with springs literally pushing their way though, and a bad condom. We actually just gave up. I was pretty happy for a do-over.
I had just dated this guy who broke up with me because I wasn't a virgin. (ALLLLLLL the LOL's!) and was with this other guy I'd known for a long time. We both had our eye on each other but were with other people at the time. We had this crazy animal attraction connection I could never explain. We were both single and had the best time together finally getting to be out with each other. I knew that the sex would be awesome. Well, it was way too soon after being rejected by this first guy....so I wasn't in the right place mentally. I was TERRIBLE that night. Plus,we had just gotten done watching the new Rocky Movie remake that had just come out (this was several years ago)...and well the DVD was stuck on the theme song. (You know how they do when you're done watching the movie. It replays that intro music where you can either hit play or select to watch certain scenes). So I was terrible...and "Eye of the Tiger" played repeatedly in the background on repeat.
Saying my girlfriends cried literal tears (obviously, while laughing) after I told them this story was an understatement.
I can't think of a specific time. I will admit though that there was no sex on my wedding night. Or probably several months before and after. My mom died 11 months to the day we were married and I was a bit of a mess.
A red eye flight over the Pacific during our honeymoon. We tried out for the Mile High Club and while we got our member badges, it only lasted for about 30 seconds. It was awkward and cramped and smelled like farts in there.