Men Share Times They Actually Regretted Having Sex

Men Share Times They Actually Regretted Having Sex
Men Share Times They Actually Regretted Having Sex

Getting some isn’t always a good thing—even for dudes.

That sinking feeling in your stomach whenever their name comes up; the face-palm you do at the very sight of their Facebook profile. Many women have someone from their past who they wish they could build a time machine to go back and “unsleep” with. What about men, though? Conventional wisdom tells us that with the “Y” chromosome comes a fixation with sex that knows no bounds. Is it even possible, then, for a man to do the deed and then wish afterward that he hadn’t? I talked to five of my close dude friends and found out that the answer is a resounding “yes.” Here are their stories. (Note: Names have been changed to protect the repentant.)


Friendly Fire:

“I had a platonic girl friend who was going through a rough breakup around the same time as me. We used to commiserate with each other, and conversations often turned to how lonely we both were. Eventually, we ended up having sex a few times. It was confusing because we had been hanging out a lot already, and I think after we had sex, both of us got confused about what was going on. We went out to dinner, and she told me that she had developed feelings for me and thought maybe we could date. I didn’t know what to say, so I started laughing nervously. She got really upset, and I felt like such an a**hole. Our friendship has never been the same—it’s basically non-existent now—and I still feel really bad for hurting her feelings.” —Joe


Family Matters:

“For a while, I was hooking up with this woman who lived about an hour away, so I would go see her when I was headed that way for work trips. One night, I was driving out and texted her to tell her I was stopping by. She told me to come on over. When I got to her place, she didn’t answer the door, but  I felt like we knew each other well enough that I could just walk in. So I opened the door and decided to surprise her by getting naked. I was in her room, totally naked, when I heard her walking around downstairs. I called her name, and a teenaged boy’s voice answered with a terrified ‘Hello?’ I had no idea she even had a son! I scrambled to get my clothes on faster than I ever have in my entire life and hauled a** back out to the car. If I had known there was a kid living there, I definitely would have just waited for her. With my clothes on.” —Gary


Bros Before:

“I hooked up with a buddy’s ex-girlfriend, which I knew at the time was a bad idea, but she was really hot—and I guess I just thought if we could keep things on the down-low, it wouldn’t be that big of a deal. Eventually, months after we had hooked up, the two of them started talking again and got into an argument. She told him that we had had sex. My friend was devastated and—understandably—really pissed at me. What could I say for myself? I had obviously violated guy code. Some time has passed, and he and I are cool now. But if I had it to do again, I would never have slept with her in the first place.” —Alex


Like a Good Neighbor:

“There was this girl I used to hook up with who lived in my dorm in college. After we’d hooked up a few times, it sort of started to seem like she wanted more. She would get bummed out if we didn’t hang out on Friday night and always wanted to be texting back and forth. I thought she was cool and we had fun together, but I was 18 and at college for the first time—I just wanted to be hooking up with a lot of people. I should have done the mature thing and told her I wasn’t looking for a relationship, but again, I was 18 and just kind of started ignoring her texts, even though I obviously was going to see her since we still lived in the same building. A few months after the fact, I heard from a mutual friend that she was really upset with me. She still shows up in my Facebook feed sometimes, and when she does,  I always feel bad for not treating her better.” —John


Working Relationship:

“I was just out of college and had gotten my first decent job. Not only was I finally working, but my boss was this hot older woman with whom I was pretty flirty. We always used to walk out to our cars together, and she would frequently send me suggestive instant messages. One night, post-after-work drinks, she and I went out for another round. One thing led to another, and before I knew it, we were hooking up. The next day at the office, rather than singing my praises and giving me extra attention, she barely looked at me or acknowledged me at all. It was pretty awkward after that. I felt weird around her, and I’m sure she felt the same way about me. It was just a really bad dynamic to have with your boss, and I basically ruined my first professional experience with one bad judgment call. I work somewhere else now, which is mostly unrelated, but I still wouldn’t do that again.” —Steve



Men Share Times They Actually Regretted Having Sex