Ex Confessions: A Real-World Guide to Sleeping With Your Ex

A tale as old as queer time: the inevitable moment you end up hooking up with your ex. It seems most of us fall into this at one point or another — we don’t mean to, at least most of the time. But as creatures of comfort and habit, and seeing as we all often hang out in the same community, it just happens! There are times where this can work out easily enough; maybe it’s been a long time since you broke up, and you ended on good terms and have been friends since. Maybe you only dated for a short time and no one’s heart got broken, you just faded into a healthy friendship. Maybe you both are just like, really mature direct communicators with healthy boundaries who know how to have a sexual relationship that doesn’t have to bring up loaded feelings! But, more often than not, it’s probably not the greatest idea to sleep with your ex. I’m not here to scold you at all, I’m guilty of this, too. This is probably not a good idea. BUT! The body wants what it wants and it’s okay for us to make mistakes sometimes and gosh darnit, if we’re going to do this thing we might as well do it as consciously as we can.

Still, before throwing caution to the wind, because FUCK IT this is already kind of a mess so WHATEVER, maybe consider some things:

We are never ever ever getting back together

This is meant to be fun and easy and not loaded, right? From the beginning, be honest with yourself (and your ex) about how you’re feeling — if there are still heart feelings lingering, REALLY consider if this is a good idea. Even if they feel like they won’t get in the way, even if it feels like a small enough amount to not interfere, remember that you’re re-entering an intimate space with someone you used to have a relationship with, and that can bring those feelings back up to the surface. If it’s more than just physical intimacy with a person you are comfortable with, it might not be the right choice for you!

Be really clear with your intentions. This is not dating. This is not you relighting the relationship flame. This is two people having fun, enjoying each other, and then continuing on as friends or acquaintances or maybe even enemies?? I don’t know, it’s your life. If someone were to ask you “What’s going on with you and (your ex)?” and your answer is something along the lines of “It’s complicated!” maybe this isn’t the dynamic for you!

This should be the first conversation you have: discuss honestly with each other how you’re feeling. Negotiate your boundaries around this. Is it chill to make out at parties, or is this more of a ~behind closed doors~ deal? If one of you starts to have feelings, how do you proceed with ending things in a way that feels good for everyone? Should you set a cap on the amount of times you can hook up in a week, to avoid spending too much time on each other? Are sleepovers okay? Cuddling? Have the hard conversation first so the fun can come! Having sex is meant to be FUN!! Having boundaries around sex with a person who played a significant role in your life who is now stepping into a new role is also FUN!!!

So what are we?

I mean, fair question! You know you aren’t back together, we’ve covered that, but this is more than a casual hook up in a lot of ways, because your past history unfortunately makes it more than just casual in its casual nature. There are definitely some ways to keep that in check — be careful with the time you spend together. It’s cool if you are friends too, that can be great! Every dynamic is different. But if you’re spending one-on-one time together that isn’t hooking up or checking in, then like, is it a date?? Just something to think about! What are you getting from that time you are spending together that isn’t sexual or friendly? Watch out for those creature comfort feelings. It’s so easy to fall back into relationship patterns with someone who you once shared that kind of space with.

So what are you then! I find it is easier to sort what you aren’t, because tbh figuring out what you’re actually doing can lead to conversations you might not want.

Is this hot or weird?

I have absolutely asked myself this out loud when I’ve found myself entangled in this dynamic. Sure it’s hot, or why would you be doing it? There’s something very hot about messing around with someone you know you shouldn’t. And listen, weird does not have to equal bad, it’s just… weird. I’m a big fan of pro/con lists when I reach this point. Am I having fun, is this worth my energy, does it feel good or is it more stress than good, etc. This could be a good thing if you keep yourself in check. If it’s more weird than hot, consider changing your dynamic or taking some space.

On another note though, leaning into the hot-weird can be more fun. There’s a flip side to just about everything and this is no exception. Get hot AND weird.

Speaking of Pro/Con lists..

Feeling confused? Totally understandable! Let’s break it down and simplify!

Do the damn thing if:

– You and your ex are communicating clearly
– Your ex no longer has lingering feelings
– You no longer have lingering feelings
– There’s no confusion or misunderstanding about what you’re doing (and not doing)
– You’re having fun!
– You can exist in public spaces comfortably with clear boundaries
– Jealousy re: the other person’s sexual partners is either non-existent or easily talked about and managed
– Everyone feels this can progress comfortably

Consider disengaging if:

– Someone is feeling an imbalance about feelings
– You are spending more ~intimate time~ together that falls in a gray area of not a date but not platonic either
– Jealousy comes up negatively re: the other person’s sexual partners
– You’re processing more than you’re fucking
– It’s more work than it is fun
– Boundaries get blurry
– There’s difficulty when sharing space publicly
– It has become more about creature comfort or old routines than having a good time
– Things are feeling loaded
– There are nervous or negative feelings about how things might end/ how things are going

There are, like always with matters of the heart and body, so many moving factors to keep in mind when maneuvering through a dynamic like this one. For the sake of simplicity though, even just starting with a simple checklist can help make those decisions easier or more clear.

Ending on a high(ish) note

All semi-messy things must come to an end, at some point. You know it, I know it, your ex knows it. Like any relationship ever, it’s hard to know when is the right time to end things. And when it comes to something of this nature, it might even feel silly to have to end things, because what even was it, ya know? Do you really need an ending? Maybe not! But due to the specific circumstances, consider that having a clear ending to your situation is probably the best way to carry on a friendship without any confusion or boundaries being accidentally crossed.

The timing is up to you, of course. But for myself, I have some rules. How long has it been going on for, and how often have we been hooking up? If, say, it’s fallen into a pattern of only hooking up because it’s easy and not because it’s the most fun, I might decide it’s time to terminate it or have some intentional space. Keep it light and remember this isn’t actually a breakup, so it doesn’t have to be treated as such. Just a chill conversation about a shift in your dynamic. Now you can be friends! Chill!

So! Be safe, state your needs, keep hard boundaries. And remember to prioritize yourself always. You deserve to get laid if you want that and you deserve for that to be on your terms. Go forth, be messy, and have a very happy hook up!

If you’re still having some feelings about it, here a little playlist (made by my actual real life ex!) to support you in this time. We are all here for you!


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Courtney is a budding sex educator, performer, and writer based out of Portland, Oregon. She spends her time slinging sex toys at the local female-owned queer-friendly sex toy boutique, being a dutiful intern on the podcast Sex on the Brain with sex educator Amory Jane, singing at the nearest variety show, writing way too personal things for the internet, dancing at the queer party down the street and buying lots of cheese. She can be found tweeting about tinder and astrology @courtneykist. She just wants you to have a good time.

Courtney has written 10 articles for us.


  1. I was really hoping this would validate some decisions that i know are TERRIBLE decisions. why would you make me think about the consequences of my actions??? (note, i didn’t do anything, i just super wanna fool around with my ex and it’s a bad bad idea, especially according to these guidelines)

  2. “Go forth, be messy, and have a very happy hook up!”

    L O L COURTNEY!!! write this on your tombstone plz i love you for forever <3

  3. Well, now I need “consider disengaging if you’re processing more than you’re fucking” on a pillowcase.

    • Definitely came to the comments to say the exact same thing. I wish I had read this gem a couple years ago, would’ve saved me months of heartbreak and sexual frustration

  4. I love the tone and the advice, and this is basically the kind of friend I want to be when my friends are making some quesssssstionable decisions. (also when I’m making questionable decisions)

  5. Restored my relationship, my boyfriend came back to me, (Loverelationshiphelpcenter@gmail. com) This is the best service to use.,?????????

  6. 13 years of marriage my husband was filing for divorce because of his new secretary who was employed October 2020, this daughter of Jezebel has turned my husband against me and his entire family. My mother-in-law has called my husband several times to come for a family meeting but he said he has nothing to talk to anyone about that has made his decision, he said he has been blind all these years and now he can see that I am not the woman for him after 5 children. I was in my mother’s house with my children for over 7 months, just 4 weeks ago I sought spiritual aid to stop the divorce and bring my husband back to me though all hope was lost of regaining my marriage. I’m still surprised till now about this miracle. Within these few weeks priest Adu of solution temple was able to put an end and stop the divorce and restore my marriage within 7 days. I really appreciate all the effort made by priest Adu Once again I say thanks for your help. I will drop his contact for the usefulness of those that need his help. ( solution- temple.webnode. com )

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