Please Advise: How can I start sleeping around again, without devastating my ex?

A Nerve reader enjoys her newfound single-dom, but worries about her ex-boyfriend.

Wise Readers, 

Each week, the inbox of our venerable advice columnist, Miss Information, is flooded with queries. And although she makes a valiant effort, she cannot answer them all. To deal with the surplus, we've decided to turn to you. So, don your spectacles and help this woman out. You can give her advice in the comments below, or, if you'd like to share what you wrote with your friends, on our Facebook page


Dear Nerve, 

Six months ago, my boyfriend of seven years and I broke up. We had been living together for five years. Though the breakup was mostly mutual, I was devastated. I was eighteen and he was nineteen when we met, and we broke up partly because we both felt we were in a quarter-life rut, and decided that we need to experience adulthood outside of the context of our relationship. We tried very hard to be caring and supportive of one another throughout the breakup and neither of us wanted to hurt each other. He left town for three months after we moved out of our place, and he just recently returned.  

About three weeks ago, while he was still gone, I had drunken sex with one of my platonic male friends who I have known for over ten years. This friend also knows my ex, and we are all close. My friend and I are both single now, and the sex was really great — it feels so good to have casual, hot, no-strings sex after seven years in a long-term-relationship! We hooked up again about a week and a half ago for another booty call. I have been feeling less depressed and much better about myself since I slept with my friend, and it's really helped me to start to let go of my ex and imagine a future with other men. 

The problem is, now that my ex is back in town, I am racked with guilt over sleeping with my friend. I'm terrified that my ex is going to find out and that it will really hurt him. At the same time, my sex life is none of his business anymore, and I really want to keep a casual thing going with my friend since I feel like it is helping me move on. It's also keeping my sexual appetite satisfied without the complications of another relationship, which I'm really not ready for yet. Do you think I can keep sleeping with my friend without hurting my ex? I feel so torn between my loyalty to my ex and my desire to be selfish and enjoy my new single-dom. Part of me thinks I need to just cut off contact with both of them and work on myself.

— Do I Need A Man-Cation?

Help her out in the comments below. Got a question of your own? Email

Commentarium (60 Comments)

Aug 04 11 - 12:52am
Wiser Now

Purge out all reminders of your ex and stay focused strictly on the present and future. You need about two years' worth of casual booty calls.

Aug 04 11 - 12:59am

It's nice that you're trying so hard to stay friends and keep in touch and all that, but if you're serious about your relationship being over, then you really need to give yourself the license to sleep with whoever you want to without worrying about how it's going to hurt someone who isn't even in that bed. Especially if it's helping you deal with the breakup (and you and your friend are both clear on the no-strings attached policy), I say all speed ahead with the booty calls and let the old boyfriend wince a little. As you may have discovered, there's a big gap between "devastated beyond recovery" and "hurt for a little while." UNLESS...

Okay, it's a bit of assumption on my part here, but did your breakup involve lots of long, long talks about your emotions? And lots of tearful going in circles about where you are and why it's just best for you not to be together, and blah an blah and blah? Hey, I'm not mocking - I've SO been there. Y'all were together a long time and seventeen to twenty five is a lot of change, and a lot of time to let go of. You talked through what you needed to talk through. Now is part where you move on, meet new people, and get yourself out of that slump like you promised. If the guilt over sleeping with a mutual friend leads you back into thinking about the breakup and your ex, going over those conversations again in your head, or if you feel the need to talk to him about it, then maybe you'd better hold off on the hookups until you can find someone who isn't part of the circle, if not to sleep with than just to talk to about things that you like, things that have no relation to your ex. "Working on yourself" doesn't have to be done all alone, ya' know?

Aug 04 11 - 1:13am

Ditto on finding a booty call who's not friends with the ex. If you absolutely feel the need for casual sex (we all do sometimes), make sure it's with someone outside your group. I've hooked up with exes' friends before, and the worry that I'm going to get a furious phone call at some point outweighed the memory of the fun sex.

Aug 04 11 - 1:08am

I am an advocate of the working-on-yourself. You were in your relationship for so long--and for such an important part of your life--that you might not know what you're like as an individual adult. You said as much yourself, and that this was one of the reasons for the breakup. Really, it sounds like sleeping with the friend is just giving you another man-related headache, when you should probably be joining a book club or going out dancing all night or taking up quilting. Whatever it is that makes *you* happy. Figure that out, and you'll be a much, much better partner for someone else in the future. (And if you get sexually frustrated--and you will--invest in some fabulous sex toys. The practiced use of which will, once again, make you a better partner in the future. )

Aug 06 11 - 12:24am

I predict this chick will be in a new serious long-term relationship within 3 months. For the most part, and for as much as we buy into self improvement, we usually fall into old patterns because they're comfortable. Doesn't seem like she's all that committed to working on herself if she needs another man as the bridge to "move on" and is consistently hooking up with that same man. Being "alone" without always feeling lonely takes confidence, self-discovery, experimentation, risk-taking and time. Leave the boys alone for a while, get a good vibrator, learn to feel beautiful without a male constantly mirroring it for you and go into the next relationship a more authentic version of yourself.

Also, if the guy you're sleeping with has loyalties as a friend to your ex, then I would say it is not a good situation. If you must swing wildly from branch to branch making up for lost time, then do so outside of the immediate circle of your last branch.

That is all.

Aug 04 11 - 1:36am

I just want to play Devil's Advocate; do you think he left for three months and did not fuck someone else?

Probably not.

I disagree with CS, above, because you know what? You sounded like you LIKED fucking someone who wasn't him. So it's totally OK to go out and get your rocks off with this dude; I would recommend against dating him, of course, but fucking is good.

It's kind of you to want to spare him but that ache will eventually diminish, as all things do with time and in the immortal words of a certain Canadian rock band "If it feels good, do it. Even if you shouldn't. Don't let people mess you around."

Aug 04 11 - 7:55am

"I really want to keep a casual thing going with my friend since I feel like it is helping me move on" I have to say that perhaps that isn't the case.

If you are clearly expending so much energy thinking about your ex, worrying about what they might think, needing to be "loyal" to them (like a little puppy dog i imagine?) that clearly it isnt helping you move on at all.

However , I think you've hit the nail on the head in your last statement, work on yourself. If you can continue sleeping with whoever, without constantly worrying about what any other person may think, feel or perhaps even judge you, then you should do so.

If however every time you fuck someone you seem racked with guilt, then maybe take a good long look in the mirror and identify the bits of you that you dont like and need changing, then do it.

Keep it kinky

Aug 04 11 - 8:10am

If you're going by the logic that your sex life is none of his business (which I agree with), you're certainly under no obligation to inform him of your activity. However, since you picked a mutual friend to sleep with he's probably going to find out, especially if you keep doing it (good luck keeping that relationship casual, by the way). If he finds out, it's going to hurt him.
You say you're torn between what you want and hurting your ex, but you've already decided what's more important to you. That's ok- you actually did things in the right order by breaking up first and THEN sleeping with your friend. But you can't expect everything to be hunky-dory with the ex. He's entitled to his feelings just as you're allowed to sleep with whoever you want.
This all sounds like very normal and relatively above-board breakup activity to me. There's a reason why people get hurt during these things- it's pretty much inevitable. Learning how to deal with it is part of growing up.

Aug 04 11 - 8:51am

My advice would be to become a Jehova's Witness and go door to door and worry about something other than getting laid.

Aug 04 11 - 4:07pm
T Paine


Aug 04 11 - 9:17am

How your ex feels about who you sleep with doesn't matter. Its none of his business. Period. He's your EX, he lost all rights to feel anything about who you sleep with.

You're stuck in the habit of letting his feelings effect your decisions. That's fine when you're together, but you're not, so stop it. Move on. Its your life now, you are single, sleep with who you want and feel good about it.

Aug 04 11 - 1:42pm

CF's advice is spoken like someone who's either never been in a long-term relationship or someone who's never gotten out of one still caring for the now-ex. Either way, the supposed question is: can this be done without hurting the ex? The answer is, of course, no. But especially no if you take into account the mutual friend factor and the inevitable insecurity that will cause about the reasons for the break-up. But she knows all this. She's looking for absolution. She just wants to feel better about it, for someone to say, "this is all about you and your HEALING! Don't you worry about what he thinks." So, nicely done, CF? Anyway, she suggests the answer she wants in her letter, she just wants someone else to say it. The fact is, she's making a decision that is hurtful to someone she supposedly cares about (does anyone argue that it would be extremely hurtful to find out your girlfriend or boyfriend of several years started fucking one of your friends within a few weeks?). She has a right to be that selfish asshole, now that she doesn't have obligations, but she should stop looking for someone to tell her she isn't one. Own it.

Aug 05 11 - 8:11pm

Yup. This WILL come out. You should absolutely feel free to do whatever you'd like but don't think that it won't have deep consequences for both him and yourself.

Aug 04 11 - 9:43am

I say you're just another no good lying bad slut whore.

Aug 04 11 - 1:19pm

Looks like the Ex reads Nerve! Either that or somebody has some serious woman issues. What's the matter baby, did your WoW gf dump you?

Aug 04 11 - 1:19pm

...just like me.

Aug 04 11 - 9:54am

Your relationships with your ex is pretty unhealthy. It might seem good and mature and adult to stay friends with him, because you were so important to each other. But you're not friends. You're still treating him like he's kind of your boyfriend, or might be your boyfriend in the future. You probably still have some residual feelings for him, which is normal and natural and not something to beat yourself up over. But you do have to fully get over him before you can move on, even to casual NSA sex. And if that means that you can't be friends right now, that's what you have to do.

And I definitely don't think you have to take a "man-cation." It sounds like you really enjoyed the casual sex, which is great. There's no reason to deny yourself something you enjoy in order to "work on yourself" -- casual sex shouldn't take too much time from your book club/knitting/long, soulful journaling sessions or whatever. And the advice to get a new fuck-buddy is not wrong, because that would be the ideal -- but someone who is able and willing to keep up a casual relationship, who
s good in bed, and gets along well enough with you that the before-and-after conversations aren't awkward, is a rare gem.

Aug 04 11 - 10:16am

If you two are broken up, and it was mutual and respectful as you said, then he should not care that you had sex with someone else. And you should not sit around worrying about what he may or may not think. So either you're being dramatic or not giving us the whole story.

Aug 05 11 - 8:23pm

Someone else, no. A mutual friend, yes. Speaking as someone that has gone through this, finding out your ex has slept with someone else sucks. Finding out your ex has slept with a close mutual friend effects the dynamic of your entire circle of friends. People are forced to choose sides and it can get really ugly.

Aug 04 11 - 10:20am

Short and sweet. Stop overthinking this. You're now single, he's single. Do what makes you feel happy and all will work out in the end (no pun intended).
He'll do the same.

Aug 05 11 - 8:56am


Aug 04 11 - 10:23am

I was in your exact same situation, almost word for word and, speaking AS the boyfriend, the quicker you move on with your life and do what you're gonna do, the quicker he gets through the grief. Trust me, in the long haul it doesn't do you any good to build you actions around his emotional state.

Aug 04 11 - 1:21pm

Good point, Joe. He might still be holding a torch for you and since you're not getting back together, it would be better for him to extinguish that flame sooner rather than later.

Aug 04 11 - 11:35am

Do what you need to do to get over your ex. If that means sleeping with someone else, so be it. At this point, it is not your ex's business what goes on in your pants anymore.

However, a little consideration wouldn't be out of line. Don't rub this in his face. You don't have to lie about what's going on, but try and keep the booty calls with the friend out of sight. Also, what others have said about trying to find a FWB that isn't a mutual friend is good advice. There has GOT to be some other attractive guy in town who isn't friends with your ex who you can bone.

And if you still feel really badly about the breakup a few months from now and seeing your ex is driving you crazy with guilt, please consider moving away fora while/permanently. No job/town is worth your sanity.

Aug 04 11 - 12:30pm

" sex life is none of his business anymore..." Exactly. Don't worry about your ex. Part of moving on is to begin to care about his feelings less. You won't do any unnecessary harm if you don't brag to your ex that you're having sex.

And your ex is probably having sex with other people too.

Aug 04 11 - 2:11pm

"And your ex is probably having sex with other people too."

Word. But maybe he has the good sense not to sleep with someone in their group. I can tell I'm in the minority here, but if I split with my partner (we've been together for about as long), I would make it a point not to sleep with any of our mutual friends for at least a little while. Or I'd make damn sure it stayed secret. Unless we split in acrimony, I'm pretty sure I would try to fulfill my sex drive without doing something so likely to hurt my partner. It seems mean.

Then again, what the hell, nothing like a clean break, right? Just do it. All bets are off: you don't owe him shit. Those seven years mean nothing and he is basically not a person that you should be concerned with on any level at all anymore. Now that you're not his girlfriend, anything you do, as long as it feels good, is by definition okay.

Aug 04 11 - 11:06pm

So you would only sleep with a mutual friend after an acrimonious breakup? That sounds more fucked up to me.

Aug 04 11 - 3:40pm
Redflag Minor

First of all. Don't worry about what your ex does. That's no longer your business or concern. Secondly to answer your question, YES. You are a SINGLE woman now. Their is nothing wrong with having a good time with other people!

However i wouldn't sleep with another man just to intentionally hurt your ex. Don't stoop to that level. You need to move on... The transition period after a breakup can get real messy if you guys don't respect each others freedom and me i know from experience..

Aug 04 11 - 3:49pm

You're used to considering your ex's feelings, but you're single now, and you need to adjust your perspective. Yes, he will be hurt, and no, that shouldn't stop you from doing what you want/need. That's the new normal of being single that you need to adjust to. That said...this "casual hookup" thing with your friend is going to get messy, honey. Your ex will find out through mutual friends. He'll be more hurt than he'd be if it was a stranger. Your friend group will gossip. Drama will run rampant. And you, meanwhile, will develop feelings for your friend. You will fall into a relationship with this friend, because that is what feels normal and safe to you - being in a relationship. You will further delay the "single life" you think you want/need by spending a year or more rebounding in another "serious relationship" with this friend. I would advise against going down this road, cut things off with the friend now, and find some stranger to hook up with.

Aug 04 11 - 3:57pm

What you don't know is that your ex too is sleeping with the same mutual friend....

Aug 12 11 - 2:40pm

Good one !

Aug 04 11 - 4:05pm

Our association with others changes us. The portion of your brain that you used during your seven year relationship is still there, and it still relates sleeping with other men as something that might be hurtful to that former boyfriend. But that is past now, isn't it?

Anything you experience from this point onwards is solely your business. Granted, it might have been better to select from available men outside your close social network, but this kind of thing happens. Guilt is not applicable here. You must move on with your life.

Aug 04 11 - 4:41pm

One other thing to keep in mind is that the friend is certainly aware of the situation. The guilt you feel is understandable but more bothersome to me is the friend's participation. I have many friends who have attractive partners and I would never consider seeing any of them if their relationships ended. You definitely consented to sleeping with this person but you were also in a post breakup fragile state. He obviously isn't that good of a friend to your ex or you probably wouldn't be in this position. Another thing to remember is that your ex is going to be hurt when he finds out you slept with someone other than him regardless of when or with who it happened. It's just unfortunate that it was with someone he considers a friend. As everyone else has already said, you need to get past this old relationship and if sleeping with your friend helps then good for you. Your ex is no longer your problem however he is still your friend's.

Aug 04 11 - 6:00pm

Just fuck whom you want to. And expect him to fuck whom he wants to. Yeah, you both might get a little hurt that way, but so what? You'll both get over it.

Aug 04 11 - 9:09pm

You know what? It might hurt him. That's life and it's something that he's going to have to deal with. That's part of growing up and being an adult- dealing with breakups and respecting that the other person is moving on. That doesn't mean it's easy for him - but that also does not mean that you should give up something that is good for you and makes you happy.

Be respectful and honest. Maybe you could call your ex and tell him what is happening? That might be less painful for him than hearing it through the grapevine. You're not required to do that for him but it seems like you care about his feelings, so it's a thought. Don't let him guilt-trip you, though.

Your dating life is just starting. Have fun! Be safe, but do what you want to do.

EM Forster wrote something like: No matter where you stand you are going to cast a shadow. The only thing to do is to stand as straight and tall as you can and reach your hands toward the sun.

Aug 05 11 - 2:13am

The only thing that matters in this situation is who was friends with this friend you're sleeping with casually. Because your letter says both you and your ex are friends with this guy. IF this guy was friends with you first, fuck away. Your ex has absolutely no stake in this and if he gets upset, it's not your problem anymore. But if this friend was introduced to you by your ex-boyfriend, he's in trouble and you're in trouble. Your ex has a stake in this because not only did you sleep with his friend, but his friend slept with you. The bro-code has been violated. If this is the situation, friendships are going to be lost on pretty much all accounts. The only way to avoid it is to avoid both of them, and even that probably won't help. The phrase "sloppy seconds" might exit your ex's mouth once or twice, two.

But, like I said, you're home free if your friend was yours first. Your ex might get upset once he learns or figures it out, but you shouldn't feel any guilt over that. He's the one who'll have to deal with it, not you. Unless he gets stalker-y and you'll have to call the police on him.

But I digress. Enjoy your single-dom and be safe. But don't feel guilty if you're handling things properly.

Aug 05 11 - 8:36pm

I know the "bro-code" is a fact of life, but that doesn't make it less sexist. You can't date or sleep with a girl your bro dated or slept with, why? Because he "owns" her or something? Please give me a reasonable justification why anyone should abide by this "bro-code."

If her ex says "sloppy seconds" then he is a disgusting pig and she's better off going ahead and hurting his "feelings."

Aug 06 11 - 3:31pm

no he doesnt "own" the girl but just as girls dont sleep with friend's ex boyfriends its out of respect to your friend. unless you and that person have such amazing chemistry and you know you are fated for life then you ask your friend first before you proceed. even though you arent together anymore people still consider their past loves theirs- and if someone you care about goes after them then its a double slap in the face. sadly this can be true even years later after they have moved on.

Jun 10 12 - 8:41am

I wouldn't call it "sexist." It's a rule for a reason.

The "bros-before-hos" rule really only applies to guys who are really close friends with the "bro" in the equation. (This also applies to women, too, so keep that in mind.) She just broke up with her ex-boyfriend and admits that she isn't over it yet (thus the post-breakup one-night stands). Her ex is also not over her. No, her fucking someone new is not his business... but the fact that it's a close personal friend kind of draws him into the equation.

Bros do not fuck their other bros' hos because their bros are, almost literally, their bros. To fuck the bros' hos would be incestuous and, to some extent, very very creepy. (Does that make sense?) This friend has been personally involved in their lives for long enough to be considered "close"; whether that closeness extends to the ex or not is for the OP to know, but if it does, she is potentially causing catastrophic drama in their social circle. Depending on how over it the ex is, or how douchey the friend is... well, you kinda gotta assume the worst-case scenario (i.e., the breakup becomes more acrimonious, friends take sides, everyone's slinging insults, just a gigantic bloody mess).

My advice to the OP (admittedly late advice, but still) is to disentangle yourself from your friend, distance yourself from your ex, and go find other people to fuck.

Aug 05 11 - 4:48am

If your ex was the one fucking a mutual friend, how would you prefer to find out about it?

You sound like you are really enjoying new uncoupled sex. Enjoy it! You have my blessing!

And, is there a tiny part of you or your fuckbuddy who want to give your ex a what-fer? Just wondering.

Aug 14 11 - 8:21am

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Aug 05 11 - 3:12pm
Just some guy...

I find it problematic that after fucking a "platonic" friend you are "feeling much better about yourself". Forget your ex, this is about you. Sex or men should never be associated with you (or any woman) feeling better about yourself. This issue is related to your issue with your ex-BF. You may be worried about hurting him, but you are equally or even more worried about his perception of you. You have to be you. You can't be the girl that he believes you to be or possibly needs you to be. Your issue is not just "letting go" of your ex-BF, but letting go of the girl that was his GF. This has much to do with identity. Who are you?

Aug 05 11 - 3:15pm
Just some guy...

Oh, that "platonic" friend isn't a friend. I'm not saying he is an enemy... LOL The line has been crossed... He is a "fuck buddy". :)

Aug 06 11 - 1:09am

You've moved on. Good for you. Don't worry about whether he's grown up and moved on.

Aug 06 11 - 11:25am
Karolina - shock!

Aug 07 11 - 9:04am

the fact that you feel for him is still love him. Right ?

Aug 07 11 - 11:21pm


Aug 09 11 - 6:40am

It's pretty simple. Treat others as you would have them treat you. You probably wouldn't care for it much if your ex turned out to be boning one of your friends. I'm guessing you'd probably feel pretty hurt. Golden Rule and all that.

Aug 10 11 - 7:46pm

Personally I don't see how your ex can be your friend. You both may be trying pretty hard to be "friends" but the fact of the matter is that it's impossible. You sleeping with your friend shows where your morals and priorities are so there is not much we can do there. That guilt trip you got recently isn't something to be ignored, you did the wrong thing to satisfy an itch you could have scratched yourself. If you are going to take the time to find out "who you are" then don't half ass it by having on the rebound sex cause, take the necessary time alone that you NEED to truly move on.

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