The 15 Hookups We Sort Of Regret

We hate those people who smugly say, “I have no regrets.” If you have no regrets in life, you lack the ability to look back on the choices you’ve made, recognize mistakes, and take steps to do better in the future. We have plenty of regrets, but recognizing them doesn’t mean that we dwell on what we did wrong in the past; it just means we’re better prepared to not make the same mistakes in the future. That’s why we would never sleep with these 15 dudes again. Once was enough.1. The Two-Pump Chump

“This story is a good one, but though the specifics may not apply to you, many women have in their casual sex black book a dude who just couldn’t last. In my case, he lasted approximately 45 seconds. I know it was less than a minute because there was a digital clock in my line of vision and the time did not change during fornication. We met at a Halloween party. He was dressed as a chicken; I was dressed as “the walk of shame.” I went home with him, we had sex for 45 seconds, and the next day I did the walk of shame in my walk of shame costume. When I made a mad dash for the train about to leave the station, my heel broke, so I had to hobble the rest of the way. The only reason I might not regret this notch on my bedpost is because it makes for a great story.”

2. The Pathological Liar

“I had a week long affair of sorts with a guy who flattered me whilst telling me tons of lies. Once I found out, I kicked him to the curb. Looking back, all I can really remember about him was that he had massive testicles and that, my friends, is why he is regrettable.”

3. The Guy Whose Name I Can’t Remember

“I remember where I met this one-night-stand — an Irish bar in New York’s Hell’s Kitchen. I do not, however, remember what he looked like or his name. Mind you, this was nine years ago. But still. Literally not memorable equals regrettable.”

4. The Guy I Didn’t Remember, Period

“There was this guy who I ran into a couple years after having sex with him, and hit on him again, because I had no recollection of having had sex with him the first time. That probably means it wasn’t that good, but it’s not like I can remember.”

5. The Young One

“He was quite a bit younger than me but very hot, so I let the age gap slide. He showed up for drinks with a backpack and I felt like I was babysitting. He had a huge penis and obviously thought that meant he didn’t have to do anything else but let me ride that thing or impale me with it. Which he did forever … without getting off. When I tried to nudge him downtown, he said, ‘I don’t eat p**sy.’ In the morning, he asked me to start the shower for him because ‘showers are complicated.’ No more younger dudes for me.”

6. The Nerd Who Wanted Me To Frog Him

“There’s a reason why nerds have no sex appeal. I thought I was doing this dorky guy a favor by boning him and I was. When we started doing it he asked me for ‘froggy.’ I had no idea what that meant and I was grossed out by the word ‘froggy’ in bed. And then he came in three minutes.”

7. The Ex-Boyfriend

“The sex was just as uneventful when we were broken up as it was when we were going out. He still was fairly unconcerned about my orgasm. It just made me sad that I had spent time lamenting him when there was nothing to lament.”

8. The Guy With A Girlfriend

“We were on vacation and he claimed to be in an open relationship. The sex was so hot but I discovered soon after that he was not actually in an open relationship; he was a sex addict who had slept with one of my friends. The cherry on top? He had given her an STD. I felt nauseous. Luckily I got nothing from him disease-wise, but I did get thousands of disgusting text messages about him masturbating while thinking about me. Then I finally got a message that he could never speak to me again. What a loser.”

9. The Good Guy Friend

“One night I got really, really drunk with my close guy friend of 15 years. We ended up having sex, something that had never happened before. We had never even kissed. I had my period and blood got everywhere. It was so gross and unsexy. The next day I discovered that he had covered my neck in hickeys. I spent the next day throwing up and washing my sheets. I had to wear a scarf for five days. Friendship over.”

10. The Guy Who Wanted To Have Sex To His Own Music

“I really regret boning the guy who put on a CD of his own (horrible) band just as he was about to slide his penis into me. He also lied and said he was Italian, when he was really Puerto Rican. Like I cared.”

11. The Guy With Pubic Lice

“I regret screwing the guy who gave me crabs. The sex wasn’t even good! But I was 23 and he was cute and had a British accent. So, yeah. Oops.”

12. The Chubby Guy Who Had A Bad Body Image

“I’m an equal opportunity slut. Slim, chubby, whatever. Bring it on! But this one-night-stand I had who happened to be chubby was so ashamed of his body that he kept his underwear and a tee shirt on the whole time. When I tried to peel his tee shirt off, he actually SQUEALED and JERKED AWAY. It was so lame! This must be how guys feel sometimes.”

13. The Jesuit College Student Who Started To Cry In Bed

“He was considering becoming a priest. I was desperate. I practically had to beg him to make out with me like a proper heterosexual man should. One time he was playing with my breasts (or maybe it was my vag?) and he started crying. I had to hold him and pat his back. The lame part of this story is HE broke up with ME.”

14. The 9/11 Conspiracy Theorist

“Hooking up with him was fun, but I don’t know why I went on a second date with someone who seriously believed Bush was the 9/11 mastermind.”

15. The Wookie

“Once when I was in London, I met this totally dreamy hipster dude at a bar. I was already drunk, so I made sure to take pictures of him before I slept with him. He turned out to be REALLY hairy. And uncircumcised, but that’s neither here nor there. The sex was super mediocre, but I spent the next day washing my sheets over and over again, eventually having to literally pull his leg and chest and pube hairs one by one after they’d seemingly woven themselves in.”