Why Sex With An Ex Is Simultaneously The Best & Worst Thing Ever

Great sex is never a bad thing — unless it’s with someone you’ve already dated and broken up with. It might be great in the moment, but then you’re left with the realization that some of the best sex you’ve ever had is with someone you’re most likely never going to be with again. Or will you? Somehow that uncertainty is exactly what makes sex with an ex simultaneously the best and worst idea you’ve ever had.

  1. It could bring back old feelings. Having sex with an ex has a way of reminding you of other aspects of your relationship, for better or for worse. It’s hard to be that close with someone you used to have feelings for and not have it all come rushing back. It might feel good in the moment, but afterwards, you’ll be left with those feelings and nowhere to put them.
  2. You might want to keep doing it. Obviously if the sex is mind blowing, you’re going to want to do it again. Great sex is always a good thing. That is, unless it was definitely only meant to be a one-time thing and you know even though you’d love to do it again, you can’t.
  3. You might regret it immediately. In the heat of the moment, it seems like you’re making a great decision by sleeping with an ex instead of some new guy you know nothing about. But what if you do it and then realize right after you’ve made a huge mistake? That kind of regret isn’t worth even multiple orgasms and you know it.
  4. You’re super comfortable together. One of the best things about having sex with an ex is how comfortable you already are with each other. You don’t have to worry about what you look like from a certain angle, or whether he’s going to like your blow job technique because he’s already seen and felt it all. While this is obviously a good thing, it has the potential to spark feelings you thought you’d left behind.
  5. It’s a reminder of what you’ve been missing. You managed to forget the amazing thing he used to do with his tongue… until he does it again and you realize that’s what all the guys you’ve slept with since have been lacking. Now you’re going to have to forget it all over again and that’s not going to be easy.
  6. He knows you too well. Not only does he know exactly what you like in bed, but he knows what to say to get you going and he probably knows what you’re thinking a lot of the time too. When it comes to sex, all that of that is a good thing, but outside of the bedroom, it might not be such a good thing.
  7. You probably don’t know where he stands. If it was a spur of the moment kind of thing, it’s not like you can expect to be on the same page about what it all means. You can push it out of your mind to enjoy the sex, but after it’s all going to come rushing back. There’s always a chance he’s going to want the exact opposite of what you had in mind, and that’s going to be awkward.
  8. It makes it harder to move on. To get over someone, it’s usually helpful to cut them out of your life completely. If you let him back in on a physical level, there’s not much standing in the way of you letting him back in on an emotional level too. If you think it’s hard to keep things casual with someone you never had feelings for, try keeping it casual with a guy you used to be in love with.
By day, Courtney is a digital marketing copywriter living in Toronto, Canada. By night, she's a freelance lifestyle writer who, in addition to Bolde.com, contributes regularly to AmongMen.ca, IN Magazine, and SheBlogs Canada. Want to chat about relationships, Stephen King or your favorite true crime podcast/documentary/book? She's on Twitter @courtooo.