6 Guys I’ve Slept With Since My Breakup (And Why I Regret Them All)


1. “The Old Friend”

A few weeks after my breakup, I found myself depressed and lonely. I had stayed home to attend college in order to keep my relationship afloat and all those feelings of regret had started to set in. I figured catching up with friends would help pull me out of my sad phase. As it so often goes I ended up in bed with a guy I’d known for a while. There was a shortage of beds and we knew each other well, so it made sense for us to sleep together, right? Yeah, it didn’t sound convincing in my head, either. This was my first post-breakup romp and while I’m thankful it was with this particular friend I still regret the decision because I just wasn’t ready. Sex with someone you don’t have feelings for won’t break that connection you once had with someone else. Only time and personal healing can help you move on from a serious breakup.

2. “The Tinder Hookup”

The first thing my friends suggested after my breakup was joining Tinder. I had been in a relationship when it became popular and hadn’t ever really thought much about it. A guy I had been corresponding with happened to stay in town an extra week over Christmas break and we decided to meet up. Seven vodka and cranberries later, I was in his bed experiencing my first—and to date, only—one-night stand. I regret this hookup for so many reasons; the biggest being a one-night hookup was never on my bucket list. It wasn’t something I was ever interested in solely based on personal preference. I will say at the time, I didn’t know we’d never talk again and when that realization came to be I was left feeling gross and ashamed. Also, this experience confirmed my previous notions that sex is so much more enjoyable with someone you know and can be comfortable with.

3. “The Older Man”

Once I started going out more and learning to enjoy myself again I accepted an invitation to dinner. This guy was the complete package; you know the type, I’m talking perfect rebound material. He was extremely handsome and perfectly in-shape, owned a nice truck, lived in his own place, and treated me with total respect. He wasn’t looking for anything serious as he had also just recently ended a relationship and it looked to be a promising situation. In the end the chemistry just wasn’t there and we parted ways on friendly terms. I do wish I had given it more time before I got intimately involved with him because I would’ve seen we weren’t a good fit and saved myself the awkwardness of getting to know someone in such a private way.

4. “The Friend of a Friend”

One night I was invited to the city with my best friend, her boyfriend, and a friend he was bringing along. This friend and I spent the night having an overall good time. When we made it back to where we were staying my new friend and I settled onto the couch for the night and I’m sure you can fill in the blanks from there. I regret this decision solely due to details of that night not being kept private. This so-called friend bragged about our tryst for months. The thing you have to be careful with when hooking up with someone you have many mutual friends with, as well as someone who doesn’t value privacy, is the risk you’re taking that your personal life will be displayed publicly. Had this hookup been with someone who didn’t know my friends it wouldn’t have mattered as much, but people I had to face on a daily basis now knew things about my life that wasn’t anyone’s business but my own. This wasn’t only a hookup lesson but a life lesson as well.

5. “The Guy that’s your Opposite”

I think us girls are more inclined to act on trying something new after a fresh breakup, which is exactly the mistake I made. You look too hard to find someone so different from the guys you’ve been with in the past that you overlook the reasons you hang out with people that share your common interests to begin with. When it came to trying to have a conversation with this guy we were worlds apart and I relied heavily on a physical connection. I regret having sex with him because we weren’t compatible from the start and I didn’t take into account his feelings toward a strictly physical relationship. I hurt someone that was truly a nice guy because I was too focused on finding a good rebound.

6. “The FWB”

This is the most dangerous of them all if you’re not careful. It started off casual with 2AM phone calls and quickies in between classes. We didn’t necessarily cross our unspoken boundaries but we sure as hell learned how to tease them over time. Our middle of the night Saturday rendezvous began rolling over into lazy Sundays more often than not and eventually spending time together didn’t involve sex as much as it did real conversation. I didn’t mind the change in our relationship but I wasn’t sure what it all meant. In the end we couldn’t make it work because each of us worried too much about labeling it something the other might be afraid of. I think that’s why this particular situation is my most regrettable, because real feelings were involved, it almost began to feel like the breakup that brought us together in the first place. A FWB situation can be beneficial to both parties, but do each other a favor and talk about expectations first. Communication is the key to this type of friendship/relationship.

The most important thing I can take away from my regrettable hookup experiences is that you can’t force yourself to move on if your heart is simply not ready. I ended a relationship and jumped into bed with guys I didn’t always know, care about, or see a future with in order to feel something that could never be felt through just the act of sex alone. My hope in publicly sharing this part of my deeply private life is that some lost soul will read my words, and be compelled to forget the reckless ways in which they once strived to heal their beautifully broken heart, and instead put themselves back together much more sensibly than I did.