While movies and TV shows would have us believe that sex is intimate and romantic, that’s not always the case. As much as we wish every sexual encounter was a good experience, some people have serious sex regrets. Someone on Reddit asked, “Who do you regret having sex with?” More than 5,000 anonymous users responded — some of their stories sound pretty normal, while others are completely unhinged.
There are the classic regrets, like sleeping with a coworker or friend, but there are also criminals, siblings, and strangers. Here are some of the wildest stories:
The Regret is Real
“With my boss. While having sex the perks at work were cool but once I didn’t want to anymore, work became hell.” –spaceballs_xbox
“Someone I dated for a month before finding out he was married and has children.” –Rude_Suggestion_4685
“Best friends wife, (consensual threesome). They felt close enough with me to test waters for it. Well yeah things got awkward after that eventually we just split.” –CaucasianHumus
“I kinda regret how I lost my virginity. I was an awkward young man and was a 19 year old virgin. I went to an Asian massage place and paid $60 plus $60 tip and fucked a 50 year old Asian woman. Actually she fucked me. I came in like 30 seconds. Paid her and got dressed and left.” –RustyShackelford32
“I man I was dating while we were both in college. He was student teaching at the time. Years later (long after we’d broken up) it came out that he had been a sexual predator to the high school students he was working with at the time. Turns out that while we were together and had an active sex life, he was perusing, coercing (& raping) teenage girls. He’s serving time now.” –According-Support756
Cheaters Gonna Cheat
“I was 19 years old working the morning shift (6-2:30) at Target. Went into the loading area to see my supervisor, a 42 year old stunner of a woman, crying her eyes out. She confided that she discovered her lawyer husband was banging his young 19 year old Secretary. I hugged her, told her ‘it will be ok’ and without hesitation she took me into a bathroom and we had sex. Looking back I regret it because obviously the mixed range of emotions, me being the revenge screw, but at the same time that woman’s life was collapsing and needed to feel some sort of happiness.” –Czarcasm1776
“A woman I randomly met. We had sex immediately after meeting. The next day, I found out she was married.” –Soldier8_1981
“When I was 16 I began a relationship with my neighbor. She was in her 40’s then. She had kids and was married. It was my first sexual relationship. It felt amazing at the time, she was a pretty attractive mature woman. I had known her basically my whole life. I think that this was the beginning of my warped view on sex. I had a girlfriend my age, and I became pushy with her for sex. And I’d routinely cheat on her with my neighbor. I spent ages 16-20 sneaking off with this older lady while trying to maintain various relationships. That’s coming home from college to sneak around with her. Cheating on various girlfriends with a woman who was cheating on her family. Looking back, I wish that I didn’t do that. It warped my view of relationships and sex and it damaged the relationship and memories of my partners during my young adulthood. I thought I was living a fantasy. I should have said no or should have reached out to someone instead of going along with it.” –Cuck-Liger
Unexpected Encounters
“My mom was a bridesmaid at her co-worker’s wedding. I tagged along even though I knew nobody but her, the wedding party was small and inviting enough that I hung out with them in the limo shuttle etc for the morning. Ended up drinking too much at the reception, fucking off with a groomsman and banging it out on the ground somewhere on the golf course where the event was held, no protection, people were looking for us because the party was wrapping up, I got muddy, covered in pine needles, and my ass was covered in mosquito bites. Left a full pack of smokes at the scene of the crime that I never got back. The guy stalker-texted me for a while after, I discovered in the days following that I’d taken his virginity. Just overall a special kind of shame for that one.” –ocarina04
“A beautiful Vietnamese girl who worked at the Vietnamese restaurant across the street from where I bartended. Sex was amazing and she was super funny. Next day she came to the bar and introduced her brother. I didn’t think anything of it until they propositioned me for a threesome. After saying no, the brother stalked me for nearly a year.” –Veeksvoodoo
“I’ve had one single one night stand my whole life and I hated it. It was eye opening to me though that I desire a connection with somebody before being intimate with them, and that physical attraction isn’t sufficient alone.” –koocamungagowa
“I worked on cruise ships as a musician. The number 1 rule on ships is don’t have sex with a guest, or it will be an immediate firing. I did – in a public area late at night. Thankfully, no one saw, and nobody checked the cameras. The paranoia for the next week was no joke. It really screwed me up because I would have not only lost my job but also jeopardized the other band member’s jobs as we’re hired as a unit. Great fun, but extremely stupid and irresponsible in hindsight.” –shannoooony
“Drunk one night stand with my best friends crush. Felt awful in the morning, confessed straight away and he wasn’t too upset but I felt like the biggest asshole for a long time. Bothered me a lot more than it bothered him.” –Bread-But-Toasted
