It's not that I don't trust you... I just don't trust HER.
March 31, 2008 1:56 PM   Subscribe

To what extent could sleeping with my ex-girlfriend, who is now very firmly just a friend, jeopardize the acceptability/reasonability of said relationship to any future potential girlfriends?

First let me start by saying that I'm asking a very specific and focused question here. Please address it instead of what you think the issue should be. If you've got something substantial to say about the question but want to add a minor point about the collateral stuff feel free but please don't waste your time to tell me "that friends with benefits is impossible," or anything like that.

Okay so here are the details.
* I am a guy in my mid twenties and finishing graduate school.

* The Ex and I dated for almost 4 years. We broke up because the way our relationship developed in each others eyes we were Mr. Buzzkill and Ms. Irresponsible respectively, and those roles only grew more intense as the years went on with no sign of slowing.

* After we broke up we didn't really speak for about a year; however, at one point we arranged to meet up. After trudging through the obligatory awkward conversation to feel each other out, it was like instantly becoming best friends.

* That was about a year and a half ago and we're still very good friends. We talk about everything including each other's sex lives. We'll hang out in a group or she'll just come over, hangout and drink, sometimes to excess. (We don't fool around.)

Now as it stands, my relationship with her is very important to me. When I date women, I make sure to mention the Ex's existence, the duration of the relationship, and I also make it very clear that we're close, often hangout one on one, but would never get back together again. (I don't blurt it out awkwardly or anything, people tend to ask enough about previous relationships that it finds it's way out, before I enter into an exclusive relationship.)

As far as I'm concerned, my relationship with the Ex is perfectly reasonable and I should never have to choose between my friendship with my Ex (as it stands) and a future relationship as long as I've disclosed all this information up front before getting seriously involved with someone. Like many people on this site have advised, if they have a problem with it, they don't have to date me.

Recent development:

* In regards to talking about sex, her biggest complaint is how little time she really has compared to how long it takes to get comfortable with someone to let them get physical with her. It doesn't help that the last couple just weren't very good in that department. (For whatever reason she's really not interested in relationships right now; it's a "freedom of being single" thing.)

* The next time we hangout she suggests that we could hook up and I turn her down. While I have secondary concerns that it could damage our friendship, my main concern is something 100% hypothetical

Would sleeping with my Ex change the acceptability of our friendship (including one-on-one hanging out) to hypothetical future relationships? As I mentioned supra, I wouldn't have ANY problem holding my ground and getting a woman to accept that the Ex and I are now close friends whom won't be getting back into a relationship or hooking up just because we drink around one another. That in itself has been tried and tested to be true. Now, sleeping with the Ex wouldn't change any of those things in reality, it's just a situation based in convenience because I'll be leaving soon and she'd like a "sure thing good time." (And yes that's a great ego boost.)

The problem is, I think adding the fact that we started sleeping together outside of our relationship, even long after it was over, would be the thing I wouldn't be able to justify. I'm not sure but I think that if I was in that situation, that additional fact would probably make me uncomfortable with the relationship.

It all boils down to 4 months of sex isn't worth losing the future of my relationship with my Ex. Problem is I can't tell if that added detail would make as much of a difference to a future partner as I think it would. I've had the few people I've mentioned this to amazed that I would ever hold back due to this concern. What does the hive mind think?
posted by Annon E Moose to Human Relations (52 answers total) 5 users marked this as a favorite
Would sleeping with my Ex change the acceptability of our friendship (including one-on-one hanging out) to hypothetical future relationships?

I think this is the question, right? The answer to it is: It depends. It depends on the hypothetical person you have a hypothetical future relationship with. It depends on the dynamics of that relationship. It depends on your ability to explain the situation eloquently and set minds at ease. It depends on whether you or your hypothetical future someone think that details like when you did or didn't sleep with an ex prior to the new relationship is even anyone's business.

Could a reasonable person have some reason to think that you sleeping with your ex at this point is a bad idea or indicative that you don't have great judgment? Yes, definitely.
posted by The World Famous at 2:01 PM on March 31, 2008

Problem is I can't tell if that added detail would make as much of a difference to a future partner as I think it would.

I think it would. This thing you're thinking of doing isn't just about sex, you both could have sex with anyone- she said it herself, she wants to have sex with you specifically. To hear from a current boyfriend that he had rationally considered the situation you laid out and then choose to sleep with the ex would, as The World Famous mentioned, make me question your judgment.
posted by ThePinkSuperhero at 2:04 PM on March 31, 2008 [1 favorite]

i'm a girl. i have never had a problem with with a boyfriend who was friends with an ex, as long as it was strictly platonic after the break-up. i would be more wary of getting into a relationship with someone who has that close a relationship with an ex and who also went back to sleeping with said ex after their breaking up. it creates a very murky area in terms of what exactly is the relationship the guy has with the ex and potentially more drama than i would be willing to put up with.
posted by violetk at 2:05 PM on March 31, 2008

Yeah, I think World Famous has it on the nose here...there's no way of telling without knowing who the hypothetical future girlfriend is and how you're going to be able to justify it to her. But there's a likelihood that it'll be something that the hypothetical new girl frowns upon.
posted by sjuhawk31 at 2:05 PM on March 31, 2008

I agree with The World Famous: It depends on the girl, but I'm sure some girls wouldn't be able to deal with it and so in theory it would impact your ability to date those girls.
posted by delmoi at 2:07 PM on March 31, 2008

I agree with you. While sex with the Ex can be fun and great, there's still an attachment there, and if you wanna maintain a good, solid friendship, then leave it alone. Stick to the friendship. If a woman is insecure with your friendship with your Ex, then she's not the woman for you. But it'll definitely complicate things in the securest of women's eyes (and I am an extremely secure woman) if you are best friends and sleeping together (or were sleeping together, assuming that you go for the monogamy thing if/when you meet someone). Plus why risk the friendship? Ego-boost and fun nights aside, being good friends with an ex is rare and pretty neat; I wouldn't want to screw it up (and unfortunately, I'm not friends with either of my exes). I know we all get horny sometimes and whatnot, and it's certainly easier to be with someone who you're really comfortable with, but it sounds like this friendship is one worth keeping in the solidly friendship realm.

Good luck regardless!
posted by cachondeo45 at 2:08 PM on March 31, 2008

Why not just start dating again? You guys could try to keep in 'non-serious' but at least if you were "official" then you could use that excuse on future girlfriends.
posted by delmoi at 2:09 PM on March 31, 2008

You should do whatever you think is a good idea for YOU (and your ex), right now, in your current life situation. Don't change your behavior based on what you imagine future girlfriends might think. If you decide that it's a good idea for yourself, then presumably that means you have a good reason, and that should be acceptable to future girlfriends. The question about future girlfriends seems like a weird distraction from your actual situation. Live your life the way you want to live it, and expect new people who you might meet in the future to accept this.

To put it another way, if a future potential girlfriend would find this unacceptable, it would probably be because your friendship with your ex was too volatile. But don't try to predict whether some unknown person would think that. Instead, make up your own mind about whether it would become too volatile. If you think you can handle it and prevent it from getting out of control, then do it. But frankly, the fact that you need to rationalize this hook-up in such a labyrinthine fashion suggests that it's not a great idea.

On preview, the above posters have a good point, and maybe my above paragraphs are too licentious. If your question is whether it would make some girls question your judgment, I think you know the answer -- that's why you're asking the question, right? Because you know it has some potential to be an issue in the future.

But I would be more worried about potential future girlfriends' questioning your judgment based on your use of "whom" and "supra."
posted by jejune at 2:14 PM on March 31, 2008

Thanks for all the responses so far. Please keep 'em coming.

I am curious however, about how this would reflect poorly on my judgment as mentioned by The World Famous and ThePinkSuperhero.
posted by Annon E Moose at 2:14 PM on March 31, 2008

You have no way of knowing what triggers every possible hypothetical future date may have. But if this is behaviour you are comfortable with why would you want to date someone that would judge you on something YOU don't have a problem with?

As a data point, I've used the ex-with-benefits situation to much happiness on both parties part and stopped immediately upon beginning a new relationship (who was aware of the previous arrangement and did not seem jealous or threatened by my continued friendship with said ex). I think most of the people I have dated have had the same arrangement and I have never had a problem with seeing my dates with their exes. If it werern't for this arrangemetn I think the entire lesbian community I was in would have broken down. Heck, when my then-boyfriend's ex called me in a panic with nowhere to live for a month I volunteered his bed (with him in it) and we all hung out with no stress (or sex betwen them). YMMV It really depends on the personality of this hypothetical future date and how much you want to tailor your life right now to their imagined judgement.
posted by saucysault at 2:19 PM on March 31, 2008

I'm guessing you don't need the hivemind to tell you that sleeping with an ex under any circumstances is a freaking minefield (no matter how adult we all like to think of ourselves). Her needs aside, if it's sex without a relationship you desire (I'm not totally sure if that's what you want or what exactly you reasons for wanting to sleep with your ex are other than she asked and I'm guessing old habits die hard), why not save yourself the theoretical hassle and look for it elsewhere?

This may be obvious, but how would you feel about dating a woman who had a similar situation with her ex? I doubt this would be a dealbreaker for most people, but depending upon the circumstances it may cause some level of complication.
posted by mandymanwasregistered at 2:24 PM on March 31, 2008 [1 favorite]

You understand that "sleeping with the ex-girlfriend who's now the bestest friend because it's guaranteed to be so uncomplicated" scenario is a Seinfeld gag, right?

Or is that one of those things we're not supposed to talk about?

If "4 months of sex isn't worth losing the future of my relationship with my Ex" expresses your true sentiment, then don't sleep with your Ex, because I count at least four ways it could wreck that relationship, and I've seen all of them happen in real life except for the one you're worried about, which I only ever saw happen on Friends.
posted by nanojath at 2:27 PM on March 31, 2008


But I would be more worried about potential future girlfriends' questioning your judgment based on your use of "whom" and "supra."

So I'm in the middle of writing a research paper too, it's not like I didn't realize the question would sound a bit odd. It's not like I asked out loud, I'm just in that frame of mind right now when it comes to writing.

(I never know if I use "who" and "whom" right, anyone know the rule that applies to my usage above?)

But frankly, the fact that you need to rationalize this hook-up in such a labyrinthine fashion suggests that it's not a great idea.

And by the way I'm rationalizing NOT hooking-up in such a labyrinthine fashion, there's a big difference. Plus the fact that I asked MeFi in the first place suggests that I'm having a an issue I'd like outside opinion on.

And just generally, please keep the the backhand insults to yourself.
posted by Annon E Moose at 2:28 PM on March 31, 2008

I don't understand why your future partner should care that you had sex with your ex a few times in four months before you moved away. So what? Exes have sex all the time. If you're serious about someone else, just be serious about them, make sure you don't have any diseases or hangups about this former girlfriend and have a relationship with them in the present tense. Otherwise, you're just laying a big load of responsibility onto them for your previous relationship choices, which isn't all that attractive or necessary. I don't need to know the ins and outs of my SO's history unless it's an active threat to our current relationship. I'm a grown woman with a history, he's a grown man with a history. I'd just as soon he didn't ask for my blessing or approval of what choices he made before we got together, nor do I expect the same from him.

Just do it with your ex already if you think you can both manage it with your friendship intact. It's possible. It's also possible you're going to fall in love again and it will make moving all that much more difficult and will screw up your friendship. It's also possible that you still love each other and your problems could be solved if you stopped being Mr. Buzzkill and she got her shit together in other ways. All this "justifying" to a future lover just seems beside the point to me.
posted by TryTheTilapia at 2:29 PM on March 31, 2008

It reflects poorly on your judgment in the sense that you have placed yourself in a murky area of what your exact relationship is with your ex. Because from an outside perspective it could be construed that you are still with your ex and are seeking something else with the excuse of, "Well yeah, I once loved her and was with her but we are only sleeping with each other now. But you know that I would make love to you! " or that you are unsure of what you want. It also reflects possibly that you do not have clear boundaries from the past, present and future.

From a purely selfish angle, I would wonder if the drama is worth it to being with you if you have this kind of complicated back story. I would be impressed that you were friends with your ex, I would consider it odd that you are now fuck buddies with your ex. This screams drama. But reading your questions I notice that your friends find nothing wrong with this so maybe your potential future girlfriend would be OK with it. You know your people the best.
posted by jadepearl at 2:30 PM on March 31, 2008

Okay I just reread that first paragraph. It comes off real douche baggy, sorry. I just didn't want to get side tracked by the people who say friends with benefits is impossible, or simple impossible with ex's. We all know MeFi tends to get off track often.
posted by Annon E Moose at 2:31 PM on March 31, 2008

I wouldn't worry about what hypothetical potential new girlfriend would think. As others have mentioned, it depends on the situation and depends on the girl. Hey, maybe H.P.N.G. is sleeping with her ex right now!

However, it might raise this red flag: Are you really over your ex? If you've recently been sleeping with her, H.P.N.G. might take that as a sign that you're not completely over her, in the romantic sense.

Sleep with your ex if you want to and if you think you can both handle's silly to not do something because you think someone who doesn't currently exist might not like it.
posted by emd3737 at 2:32 PM on March 31, 2008

speaking only for myself, I would feel a totally different way about you and your super-close ex if you had split up and not slept together than if you split up and then slept together. I don't care if it was a week later, a month later or a year later. If you and the ex had split and not slept together again, in my mind I would assume you would NOT sleep together moving forward (however irrationally). If you had slept together post-breakup, I would worry that you'd sleep with her while dating me, or we'd have to go through a whole bunch of semantic logistics to assure that wasn't going to happen while we were dating. There's a sense in which I'd wonder why you even wanted to date if you had an excellent ex who you were sleeping with.

I don't think it says anything about your judgment. I've slept with exes before and I think a lot of people have. I think it's more if you want the ex to be a good friend as you date other people, it's a pretty good idea to make sure things are crystal clear to all involved and that sort of assessment is easier if you follow the normative pattern of not flipping an ex into a "friends with benefits" situation. I'm sure lots of people won't mind, and I'm a bit of a serial monogamist so that informs my perspective, but you seem to be looking for perspectices and that's mine.
posted by jessamyn at 2:32 PM on March 31, 2008 [2 favorites]

And by the way I'm rationalizing NOT hooking-up in such a labyrinthine fashion, there's a big difference. Plus the fact that I asked MeFi in the first place suggests that I'm having a an issue I'd like outside opinion on. And just generally, please keep the the backhand insults to yourself.

You asked about whether this is a good idea, and I gave my thoughts on whether it's a good idea. The fact that you felt the need to give a labyrinthine rationalization is a red flag. I stand by this 100%, and I don't feel the need to "keep it to myself" considering that you asked the question.

(I never know if I use "who" and "whom" right, anyone know the rule that applies to my usage above?)

You used it incorrectly. Try replacing it with "they" or "them." (If it's singular, use "he" or him," regardless of gender.) If "they" fits and "them" would be wrong, you want "who." For instance, you wrote, "...close friends whom won't be getting back into a relationship..." You would say "they can't be getting back...," not "them can't be getting back..." Therefore, "who" is needed. Also, if you're unsure, err on the side of using "who."
posted by jejune at 2:35 PM on March 31, 2008 [3 favorites]

You've heard of "friends with benefits."
You've heard of "ex-girlfriends."

Have you ever heard of "ex-girlfriend with benefits?"
posted by mikeh at 2:35 PM on March 31, 2008

Yes, it will have the effect of making most potential girlfriends think your relationship with the ex is not a reasonable one. If it really is nothing more than friendship to you, then maybe anyone who can't accept that is not the right person for you. Unfortunately for you, I do think it will be hard to find people to accept it. But I guess finding the right person is always hard.

If you don't get into any new relationships for a while after this happens (my understanding is this is proposed to be a one time thing), that will help potential girlfriends be able to accept it, because it could show that your claim that you can just be friends with her is true, even if you did have sex once after becoming just friends.

If you've got something substantial to say about the question but want to add a minor point about the collateral stuff feel free

Minor point: I might buy what you're saying if it is just a one time thing. If it does happen again, I, and most others I think, would be much less inclined to believe you.
posted by gauchodaspampas at 2:42 PM on March 31, 2008

Sex with my exes has never been an issue in later relationships for me.
posted by andythebean at 2:45 PM on March 31, 2008

I am curious however, about how this would reflect poorly on my judgment as mentioned by The World Famous and ThePinkSuperhero.

I suppose judgment is the wrong word. Maybe values is better (or maybe not, I don't know- frankly, you've built this question in a way that has made it very difficult to answer, and I have a feeling it's because there are answers you don't want to hear and I'm about to give you one). For me, when I am dating, I'm looking for as little drama as possible. If I meet a guy who has to give me this long spiel on the complicated nature of his relationship with his ex, I lose interest. I don't like being in situations like that (because all those I've seen and been involved with have ended poorly), and I wouldn't want to date someone who chose to be in one, because that suggests that he enjoys them. I don't think you need to explain this whole mess to anyone, what's past is past, but if you feel the need to explain it, it's because there's something there, and women will be able to smell that, and the smart ones will flee.
posted by ThePinkSuperhero at 2:53 PM on March 31, 2008 [3 favorites]

You could end up getting your ex-girlfriend pregnant. That will have an impact on future relationships for years to come.
posted by CrazyJoel at 2:55 PM on March 31, 2008 [1 favorite]

Thanks everyone. I really appreciate it.

Jessamyn was able to help me realize what I'm concerned about is breaking the presumption that I have the proper boundaries to not sleep with my ex who's now a friend. That presumption is a pretty valuable social construct that makes it much easier for people to deal with ex's as friends of their S.O. This realization is the exact reason I posted.

So I'm going to base my decision on having that fact in mind. I'm pretty sure 4 months of sex isn't the worth the reinforcement that would be required otherwise. But I'm gonna think about it.

And one final thing, those of you saying that sex with ex's have never steered you wrong, how close were you with those ex's?

On preview:
That's actually the kind of stuff I'm looking for. The potential reaction due to anything associated with doing this is what I'm trying to determine.

I'm only willing to get so hypothetical :P

Thanks again everyone! I'll be sure to keep reading so feel free to continue posting.
posted by Annon E Moose at 2:58 PM on March 31, 2008

I think it will make it very uncomfortable for you to maintain a future exclusive relationship and a close friendship with the ex. It sounds like you'd like both in the future. Wouldn't it be awesome if you could hang out with the current gf and your close friend the ex at the same time? Never going to happen because the current gf will likely be very distrustful of the ex's motives in wanting to hang out with you if you do decide to be friends with benefits.

You've mentioned moving away, I think, and if its the case that you'll be moving away from your ex, then it provides more finality to the relationship and is something that a future girlfriend may be more ok with.

The problem ultimately, I think, is the message it sends. Most significant others want to be just that, significant, in your life, and if you start sleeping with your ex again, you basically fulfill many of the niches of a significant other for eachother. The new girlfriend has to compete with this girl who you get along great with and are apparently recently sexually compatible with. This will make it difficult to maintain both relationships at once.
posted by wuzandfuzz at 3:00 PM on March 31, 2008

You sound like you care a lot about this friendship-- and yes, you would probably have to lose this friendship if you had a serious new girlfriend after sleeping with this woman post-break-up.

If you were the new girlfriend, would you want your boyfriend spending lots and lots of time with a woman he sometimes sleeps with? thought not.
posted by Maias at 3:01 PM on March 31, 2008

If you decide not to sleep with your ex, it's probably not a good idea to tell her it's because of the hypothetical future girlfriend. She won't think it's a real reason, and she certainly won't consider it valid. By the way, this whole scenario seems to fit with your Mr. Buzzkill/Miss Irresponsible remark. She's not thinking about possible consequences, and you're inclined to stomp her fuck-buddy fun into the ground. Go with your gut on this one. It's a buzz that needs killing.
posted by wryly at 3:03 PM on March 31, 2008

If you do start sleeping with your ex, I'd make sure to talk through what that means to both of you. If you imagine sleeping together won't bring any emotional charge along with it (whether for either or both of you), you're most likely deluded. Personally, I'd probably consider it "getting back together" for a few months. That has the double benefit of forcing you to codify the terms of this new relationship and -- I would imagine -- put a larger subset of potential future partners at ease. "We dated for a few years, broke up, and got back together a few years later, but that only lasted a few months" sounds a lot less like danger than "we dated a few years, broke up, and a few years later started sleeping together because it was convenient and familiar but it wasn't a relationship and won't happen while I'm dating you even though I still hang out and get drunk with her while you're not around, I promise."

In the end, I'd follow the advice above about doing whatever feels right for your current and future friendship. And start being communicative about it now so you're in the habit if/when things get awkward (...maybe one of you meets someone else while the other has grown attached...all sorts of possibilities), even if you feel that might cut down on the sexiness a little bit.
posted by nobody at 3:05 PM on March 31, 2008

I don't understand why your future partner should care that you had sex with your ex a few times in four months before you moved away. So what? Exes have sex all the time.

I don't agree. And I think that it will potentially be a problem in future relationships, especially since the OP wrote : "Now as it stands, my relationship with her is very important to me. When I date women, I make sure to mention the Ex's existence, the duration of the relationship, and I also make it very clear that we're close, often hangout one on one, but would never get back together again."

In many women's eyes, having a sexual relationship is "getting back together." At the least, you are going to have to work very hard to maintain your new girlfriend's trust while spending "one on one time" alone with your ex.

To the outsider, it appears that neither one of you have really let go of the relationship, and now it exists in a vague, sexual limbo that will always be a threat to your current relationship. It would be a serious deal breaker for me, sorry.
posted by The Light Fantastic at 3:06 PM on March 31, 2008

I've been in your exact same situation, and wondered the exact same thing:

Short answer : The World Famous has it right. There is no way for us (or you) to know how hypothetical future gf's may react to the history of you being "FWB" with the ex. My experience tells me, that generally speaking, most females are probably going to have an negative reaction to hearing this information (even if sex with the ex only happened once). As others have commented, the general social stigma is going to be: "You MUST have issues of some kind (still hung up on old gf) if you even consider sleeping with her again after breakup"

Longer answer:
Due to cultural/social influences, most people think its impossible to remain friends after a breakup. In fact, I'd go so far to say that most people think there is something wrong with you if you put forth effort to remain friends after a breakup. My best friend is an ex-gf that I had my longest relationship with (and worst breakup). She'll say the same thing about me. (that I'm her best friend) We are best of friends, and most people think its the weirdest most unnatural thing ever.

We've gone through periods since the breakup where the timing has worked out that we are both single and need some "benefits" without all the drama of a full relationship. The times that its happened, it worked out for us. But I havent yet entered into a new fully-monogamous relationship where I've needed to explain this history to a new GF, so I dont know how thats going to play out. However, one of the personality traits I'm looking for in a new gf is open-mindedness (and maturity). At the first hint of a new gf throwing up some big drama about my relationship history, I'll glady show her the door. (and apparently theres alot of immature people out there, cause I'm still single. )
posted by jmnugent at 3:08 PM on March 31, 2008

As a potential future girlfriend, I'd second Jessamyn's remarks: I'd feel much more comfortable with her status as your best friend if I knew you hadn't slept together since the breakup. If you value her friendship, why not find someone else to sleep with, casually?

Also, it can radically confuse things: I made the mistake of making out with an ex (who broke up with me, incidentally) who within months had fallen back in love with me (with no further encouragement and at a distance of several thousand miles) and was horribly hurt when I, all unknowing, started dating someone.

For me, it was sweet to touch and be touched and not have any strings attached. For him, it was a powerful event that convinced him he'd really royally messed up and we were Meant For Each Other.

A handful of years down the line, he's dating someone else but has confessed his deep, abiding feelings for me. Not unexpectedly, his gf loathes me, and has made it difficult and nigh impossible to hang out with him/them. For me, making out with my ex, who was one of my dearest friends, likely has destroyed our friendship, which was worth a lot more to me than a few kisses.
posted by arnicae at 3:10 PM on March 31, 2008 [1 favorite]

The Light Fantastic: "To the outsider, it appears that neither one of you have really let go of the relationship, and now it exists in a vague, sexual limbo that will always be a threat to your current relationship."

Very well put. And (no offense meant to you, TFI) I think this is how a lot of girls think.

Personally, I think the real issue here is one of the approach to relationships. If you are the type of person who approaches (and participates in) relationships from the traditional classic monogamous model, then TFI's comment is exactly correct, and sleeping with the ex is probably going to cause you more problems than it fixes.

If on the other hand, you are the type of person who approaches relationships from a modern, open, polyamorous viewpoint (and seek out partners who also do), then you probably wont have any problem at all with this type of sexual history.

Of course, your mileage may vary, all people are different, and each relationship is its own unique thing, so (as stated previously) there is simply no way to tell until new potential relationships start to develop and you get to know how those people think.
posted by jmnugent at 3:17 PM on March 31, 2008

The more important question, to me, is this one: is it any of hypothetical girlfriend's business?

For some reason, people have this desire to itemize every sexual encounter they've ever had with a new significant other and get the same in return. Just say no. If you must detail your exploits, why go any farther than saying you dated her, and the two of you have had sex. There's nothing even remotely dishonest about this.

There's really no reason why this is information that a new girlfriend would need, and I really don't think it makes that big of a difference. You slept with her when you were dating (an arbitrary designation) and you (hypothetically) slept with her when you weren't. Calling it something else doesn't really change what it is.

Most women who have a problem at all, will have a problem with you hanging out with her one-on-one regardless of the "extra-curricular" sex.
posted by toomuchpete at 3:20 PM on March 31, 2008

i would be leery of any boyfriend who wanted to hang out one-on-one with an ex he has slept with within, say, the past two years. that's arbitrary, of course, and depends a lot on the guy and the ex and the girl in question.

but in general, the tradeoff for sleeping with her while you are single will probably have to be to only see her in group settings when one of you is dating. even if you DO have the self-control, it's a lot of trust to ask of any partner, especially early on.
posted by thinkingwoman at 3:27 PM on March 31, 2008

I've been the new girlfriend in this situation, and there is no way I would trust my bf (or any guy) hanging out with his ex, ESPECIALLY if he had been having sex with her post-relationship. Immediate deal-breaker. Would you be okay if some girl you started dating had a "best" guy-friend, that happened to be a (serious) ex, and that she had sex with after breaking up, but still wanted to hang out with? Realistically, probably not. Most people say they would be fine with this until they are actually in the situation, but once there, it is intensely uncomfortable for the new girlfriend.
posted by nikksioux at 3:52 PM on March 31, 2008

I thought I'd revisit this thread to see what other people have said since I weighed in, when I was reminded of what the title is. That is also a big consideration. Maybe your future girlfriends would trust you, and would be right to. But you haven't said much about what you think your ex's motivations for this are. Is she truly not emotionally attached to you in a romantic way anymore? Is she on the same page with you? If you don't think she can separate sex with you from romantic feelings with you, and if you don't want to be any more than just friends with her, then you obviously shouldn't sleep with her, regardless of whether you can still just be friends with her. It will create all sorts of messy complicatedness that you don't want.
posted by gauchodaspampas at 4:03 PM on March 31, 2008

There's a difference between nostalgia sex and a four-month long hook-up and if a new boyfriend had recently done the latter with his ex it would have definitely concerned me. It just reeks of unresolved feelings for both parties.

I can be friends with a partner's ex but I can't imagine being comfortable around someone I thought either badly mistreated him or still wanted him. I understand wanting sex during a fallow period with someone you trust and I understand that some people can distance themselves emotionally from the sex they are having and that is okay. Yet there would be no way for me to know if you or the ex wanted sex or something more complex. So because your concern is what future girlfriends might think, I'd say don't get convex below decks with your ex -- at least not for near half a year of sexy sex sex.
posted by melissa may at 4:04 PM on March 31, 2008

I don't think I'd be okay with the ex-sex either, speaking as a girl. That's not to say that I should ever find out about it but if I did, I think I'd be concerned about your ability to maintain appropriate boundaries. I'd be slightly uncomfortable knowing that you were spending extensive time with your ex while we were dating, even if you said you hadn't slept with her since you broke up but that's more a function of how strong the trust was between you and me. So the addition of knowing that you had slept with her, anytime after you broke up that was within a year or two or our being together would be sort of off-putting.
posted by otherwordlyglow at 4:37 PM on March 31, 2008 [1 favorite]

I'm having trouble answering this question because I am hung up on this part of the info you provided:

it's just a situation based in convenience because I'll be leaving soon

Would you mind weighing in on whether this hypothetical future partner is in the new location (where I assume the ex won't be), or if you are concerned about future partners you may meet in your present location over the next four months?
posted by necessitas at 4:40 PM on March 31, 2008

Having an ex/best-friend/recent-lover isn't a dealbreaker by itself. But here are things that would be red flags for me:

1) Do you have the same tolerance for me having significant emotional connections with my male friends, some of whom are former lovers? If you have a double standard for your behavior vs. mine, that's a problem. It means you think I'm untrustworthy or that your relationship with your ex is not as non-threatening as you say it is.

2) Are you willing to talk through any concerns I might have? If we're getting serious, I might want to (calmly and respectfully) understand your relationship with your ex a little better. Obviously you're still physically attracted and emotionally bonded to her so I'll want to understand whether I should be prepared for you to suddenly act on your attraction while we're together. If you're hostile or uncommunicative about this, I'd be pessimistic about getting really involved with you. Especially if I see you as an impulsive drunk, since you still like to get trashed with your ex.

3) Does she treat me as her best friend's girlfriend or as a romantic rival? Your post title says you're aware of this potential issue. If your best friend is nasty to me or actively working to split us up, and you let that happen, I'd let her have you and look for love elsewhere.

#3 is the one whose impact on your future romantic life should concern you the most. Your ex might be mature and non-jealous and unlikely to cause future drama. But if she's not, renewing an affair increases the chance that you will one day have to choose between your ex and a new girlfriend. Being friends with an ex, even one you've slept with since breaking up, is not unreasonable. But no self-respecting woman will stick around if said ex is driving a wedge through the middle of your love life.
posted by rhiannon at 5:07 PM on March 31, 2008

If you develop a physical relationship with your ex, who (it sounds like) is also your best friend, how will she react at some point in the future to you cutting her off from the physical so you can date a new girl? It's easy to say it won't matter, but things can get complicated fast.
posted by blue_beetle at 5:53 PM on March 31, 2008

Clearly you are going to hook up with her no matter what the consensus opinion of askmetafilter is. Your question seems to be begging for an answer of "yes, go hook up with her!" and your defensive posture towards those who 'question your judgment' only confirms for me that you've basically already made up your mind and are looking for validation.

You can take what you want from that, but my suggestion is to just go ahead and sleep with her... it's something you almost 'have' to do given your mindset, and as such, you will 'have' to deal with the consequences (maybe good, maybe bad, probably a mix) later on in your life. Maybe it would be more 'prudent' to avoid doing the controversial thing, but it would probably also be a lot less... rich.
posted by notswedish at 6:00 PM on March 31, 2008


The HFP would be from wherever I go next, and I guess I should have put more emphasis on that. I've stopped pursuing long term romantic relationships for now because I've tried long distance before and it just didn't work out well. One thing I think worth mentioning is I have no idea where exactly I'll be ending up yet so that adds to the complication.


I'm just gonna assume you didn't read my last (now penultimate) comment.
posted by Annon E Moose at 6:30 PM on March 31, 2008

Let me just reiterate Jessamyn's point, which I favorited.

If I met a girl who was good friends with her ex, and was sleeping with them, I think I would feel pretty insecure about it. And as relationships go, I think I'm a pretty secure guy. It would feel really hard to compete with that person; what could I offer that the ex wouldn't?
posted by HighTechUnderpants at 6:50 PM on March 31, 2008

Who/whom: just remember that who verbs whom. Who calls whom, who gets whom candy, who tells whom the new gossip. Whom did you tell the new gossip to? Whom did you call? I told them whom I wanted to tell the gossip to.

In Russia, Lenin famously said that the most important question was "kto kogo" or "who whom" (in other words, who will act and who will be acted upon). "Whom" is acted upon by "who."

In other news, sex with the ex would make me uncomfortable, but it wouldn't be a dealbreaker. I wouldn't like knowing that you have that option and that your boundaries with this woman are fuzzy, but if I trust you, I trust you. That's just me.
posted by prefpara at 6:53 PM on March 31, 2008 [1 favorite]

Would sleeping with my Ex change the acceptability of our friendship (including one-on-one hanging out) to hypothetical future relationships?

No, or if it did, you don't want to be dating that person anyway.
posted by Ironmouth at 6:54 PM on March 31, 2008

I think it would be one thing if she were just in the group of friends you hang out with and you saw her most Friday nights out with the rest of your friends. But if you are really as close as you sound it's going to be a problem. Even the least jealous girlfriend in the world, is gonna have to think twice about a best friend/ex gf who you spend tons of one on one time with and oh you also were sleeping with up until well you met the current gf, because it in absolutely no way sounds like it is actually over. It sounds like your relationship is in some sort of weird limbo and neither of you can actually cut the cord. Now it might actually be true that its over, and this is just sex etc etc, but this throws up a ton of red flags.

The scenario in which this is really going to be a problem is you've gone out with a girl you really like a few times, you're still getting to know each other, she finds out about this (on top of the fact your are best friends with your ex), she may walk away because getting involved with you sounds seems to risky (not ready for a new relationship, still in the love the ex, liable to cheat, take your pick).
posted by whoaali at 7:56 PM on March 31, 2008

I have a friend who did this with his ex (of brief duration)- they got back together because she was going to move in six months or something anyway, might as well be together until they split locations for good. I believe the terminology he used was "un-girlfriend."

And really, that's what you've got here. How is boinking your best friend not a relationship? You're dating again and claiming not to be on a technicality.

Really, I think the problem here is that there is no way in hell a future girlfriend is going to believe you saying, "Oh yeah, we're totally over each other and platonic now, we'd never get back together romantically!" Since clearly that's not the case, your un-girlfriend being your fuckbuddy/best pal is well, going to be threatening to her.

If I were you, just SAY you're getting back together with your ex as your girlfriend again, until you move. That does come across better (and less kinda-sneaky-cheater) than saying you're just friend-boinking.
posted by jenfullmoon at 8:37 PM on March 31, 2008

Depending on circumstances, sex with an ex shouldn't necessarily set off alarm bells. None of my long term relationships hasn't involved at least one hookup after breaking up, for example. However, that normally follows on soon after the breakup, and I think it's reasonably common for people to take a few attempts before being able to successfully quit a partner.

In your case, it's more troubling: 4 years on, 1 year no contact, 1.5 years best friends, then maybe a 4-month FWB relationship?

If I were your potential new girlfriend, I'd be comfortable enough with the first three parts of that, but the fourth phase of your relationship evolution would probably have me backing off, quietly, and looking elsewhere. As whoaali wrote, just too risky; too much competition for your heart and parts.
posted by UbuRoivas at 8:37 PM on March 31, 2008

Discreet sex with the ex would have no repercussions if you could count on her not to talk about it, and you "simplified" the nature of the relationship when you talked about it with future possible girlfriends. Note that this requires you to be dishonest.

However, while being dishonest specifically about the post-breakup sex, you can still be generally honest about what STD exposure you've had recently, and also to what degree you are still emotionally attached to your ex. I'll leave the moral calculus of that decision to you.
posted by BrotherCaine at 11:21 PM on March 31, 2008

Update: I decided against FWB and followed through. We're good friends still and she's in a relationship. I'm still looking, but don't regret the decision at all.
posted by Annon E Moose at 9:58 AM on July 14, 2008

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