10 Guys Reveal Their Biggest Hook Up Regrets

To discover guys' I-really-wish-I-hadn't sexcapades, we went right to the source.

Updated 5 years ago, September 30, 2019

Previously, seven women revealed their biggest sex regrets. From sleeping with questionable guys (bosses, gigolos, losers etc.) to how they lost their virginity, their disappointing bedroom decisions had a lot to do with things they had done. Just as science predicted.

According to a study published in Archives of Sexual Behavior, women regret having sex with the wrong partners and men are kicking themselves over their the sex they didn’t have. (Can’t we agree on anything, you guys?!)

What’s behind these gender differences? Researchers say it’s because of cultural standards — and evolution. Throughout evolutionary history, not sleeping with someone is a costly reproductive loss for men, whereas women focus on the consequences, both reproductive or emotional.

Sure, I’d imagine some guys wish they took advantage of their single days more, just as women do. But what are these sexual encounters so many men have been turning down left and right? Sex regrets have to go beyond not hooking up with the hot girl at the bar for some men.

To discover guys’ I-really-wish-I-hadn’t sexcapades, we went right to the source. Turns out, they’ve had their fair share of unfavorable partners in the bedroom (and park), too.

1. The Blackmail Sex

Dylan, 24, wishes he didn’t sleep with someone who blackmailed him into doing it. “It was with a coworker from the same restaurant I worked at. Little did I know how crazy she was. I was giving her a ride home from the bar and she took the steering wheel and almost killed us. She told me to pull over to the nearest park or else she would call her brother who was a cop in the same town I lived in and tell him I sexually assaulted her. I should’ve said no, but I did it. After, she said if her birth control didn’t work she was willing to have the baby no matter what happens.”

2. The On-A-Break Sex

“Sleeping with a friend who was on a break with her boyfriend. It was her suggestion, but days later she felt so guilty that things got really awkward between us,” says Jake, 26.

3. The BFF’s Sister-In-Law Sex

“Sleeping with my best friend’s wife’s sister,” says Anup, 31.

4. The BFF’s Ex Sex

“My biggest sex regret is sleeping with a friend’s ex-girlfriend,” says Chris, 26, “After it happened she told him and we haven’t been friends since. Big regret.”

5. The Too Serious Sex

“My biggest regret is taking sex so seriously,” says Jon, 30, “sometimes sex is just ridiculous and hilarious, so you have to be able to laugh at yourselves — before, during, and after. Looking back, all the pressure I used to put on myself was such an emotional waste of time.”

6. The No-Feelings Sex

“I regret sleeping with girls that I genuinely didn’t like,” Sam, 23.

7. The Pre-Marital Sex

“I regret losing my virginity before marriage. It doesn’t sound like much but after you realize that the people you are sleeping with are not the ones you’re gonna be with in the long run. You gave a major piece of your personal self to them — and it can be hard emotionally and in some way you will always have an emotional bond. It can make it difficult to give your whole self to the love of your life,” Marcus, 23.

8. The Threesome Sex

Christian, 23, regrets having a threesome with a gay couple who overstayed their welcome. “The worst of it was when we were all done. Usually you would think that when you go over someone’s house for sex you do it then leave unless invited otherwise. They didn’t get the memo, I guess, because they ended up sleeping in my bed until 8 am while I stayed awake kind of dumbfounded.”

9. The Engaged Woman Sex

“I hooked up with this girl who was in town for a week. Someone mentioned she had a boyfriend but I assumed it wasn’t super serious, so whatever. Then I found out itwas serious afterward when she was back in California. She got engaged soon after, and I thought ‘good for her.’ Then she came back to NYC the next summer and wanted to hook up again. We did, and I sort of thought we would pick up right where we left off but then I learned about 20 new things she hadn’t disclosed to me previously. I turned her down the next summer and we no longer talk. ” Larry, 27.

10. The Married Woman Sex

“I had a close friend who I had been involved with but we still messed around while she was married. Needless to say, that blew up and we no longer talk. She’s since moved, and we’ve both moved on, but I would go back and at least change what happened after she got married. I came in between someone else’s commitment and lost a true friend,” Eddie, 22.