Dating a good friend's ex-girlfriend
January 6, 2016 1:51 PM   Subscribe

Two friends of mine broke up a few weeks ago. I've been friends with the man for something close to a decade but became good friends with his then girlfriend over the last year, as well. So it was only natural that me and her continued to hang out, unexpectedly (for both of us) getting closer to each other. We're now at the beginning of a relationship ourselves - not knowing what to do with her ex/my good friend?

It feels like we're (purposefully) hurting him, as the breakup is still very fresh and I feel like I'm betraying his friendship by dating his ex-girlfriend. I guess this is a fairly common situation, but I'm new to this sort of dilemma and don't know what to do. I'm now trying to decide between calling the thing with her off and trying to be friends again, or pursuing the relationship at the likely cost of a friend. (Putting myself in his shoes, I'd probably be hurt and angry, as well.)

Is there a way out of this with minimal damage? Has anyone of you experienced a similar situation and if yes, what did you do?
posted by anonymous to Human Relations (30 answers total) 2 users marked this as a favorite
 
The simplest answer is: ask your friend if it's OK to date his ex.

If he says no, tell her that you value your friend's opinion, and it would hurt your friend for the two of you to date, and you have to break it off.

If he gives you the go-ahead, go for it.

If you want things to get complicated and emotionally painful, wait until your friend learns of your relationship second-hand, or if you ask your friend his feelings and ignore them. Those are the ways things are going to go bad.

So ask, they're your friend so you should be able to ask them their opinion on this, no need for complicated stories -- "I know you and your ex broke up...but would you be offended if I asked her out?" Don't try to explain, or justify, or anything. Yes or no answer. Go on that.
posted by AzraelBrown at 1:56 PM on January 6, 2016 [7 favorites]


Look, in all honesty, you don't want to be involved with anyone who is just a few weeks out of a breakup. The relationship is virtually certain to be unsatisfactory for both, and not what either person actually needs. When that relationship ends, you won't have a girlfriend and you won't have the friendship of your old friend, and then what will you do?

Just give it up. Tell her that you would like to reconsider the question of a relationship after she's had plenty of time to heal and process her last one. You'll be dodging a bullet on both sides.
posted by janey47 at 1:58 PM on January 6, 2016 [66 favorites]


Frankly, I disagree with asking your friend if it's OK to date her - she's not his property, so you don't need to ask his permission.

Personally, I would recommend that you decide whether you want to proceed with the relationship, and think hard about that. The consequences are yours to own. Discuss with your new girl, and if you both want to go ahead, then tell your friend. You can't control his emotions or reaction, but you can be honest.
posted by Paper rabies at 2:01 PM on January 6, 2016 [32 favorites]


Did they part amicably, or is there hostility or rancor between them? If they're friendly, but trying to get over each other, give them time and space to do that. If this lady and your friend dated seriously for a long time, then neither one is ready for a new relationship. Be friends with both and keep things friendly for now, and give it more than two weeks before you start dating.

Keep seeing your lady-friend as a friend. If you don't want to date other people, don't, but don't move this relationship to a dating level until enough time has passed that they are both over the old relationship and ready to move on.
posted by Ruthless Bunny at 2:02 PM on January 6, 2016 [3 favorites]


There's no win/win/win scenario here, unless your friend is a super cool and together guy who isn't going to be upset by this. He might think you're a giant asshole for dating his ex a few weeks after they broke up and he's entitled to think that and there's not much you can do to mitigate it. So, it's up to you: which do you value more, the old friendship or the new relationship? You have every right and reason to make whichever decision you feel is in your best interests, but you can't control the fallout from whatever choice you make.
posted by prize bull octorok at 2:03 PM on January 6, 2016 [6 favorites]


Are you prepared to lose your friend of a decade over a relationship of a few weeks?
posted by cecic at 2:06 PM on January 6, 2016 [39 favorites]


Pause. Give it time.

If the connection is in fact meaningful enough to potentially risk your relationship with your old friend, it will survive the months needed to let the temperature drop and give her space to process her very recent ex-relationship.
posted by Keter at 2:08 PM on January 6, 2016 [14 favorites]


Dude. Call this off. You don't date a friends ex. Don't date a fresh ex. This guy has been your friend for a DECADE? Call it off. Let's the dust settle. Wait a year. Then maaaaaaybe something happens but in all likelihood probably not.
posted by St. Peepsburg at 2:08 PM on January 6, 2016 [39 favorites]


If he's truly a close friend, the caring thing would be not to date his ex.

You are within your rights to date this woman, but it would hurt him, and you would do it knowingly. It would not be the kind of behaviour I would hope for from a close friend.
posted by PercussivePaul at 2:15 PM on January 6, 2016 [11 favorites]


Without referencing my own opinions about norms and stuff, I would just point to your own words: you say he is a "good friend," and you say that you feel like dating his ex is "purposefully hurting" and "betraying his friendship," so it seems like your own moral compass is telling you that something is wrong.

My opinion: when one option is to maintain your own morality, integrity, and good friendship, and the other option is something that has a strong component of sexual desire and confusion, then be very suspicious of the second option, because it can undermine not only your relationships but your self.
posted by mbrock at 2:17 PM on January 6, 2016 [14 favorites]


Have you realized this woman is the love of your life, the future Mrs. Anonymous, and the possible mother of your children? If so, go for it, but do make a point of telling him so at least he doesn't hear from someone else and think you've been sneaking around. He doesn't own her and no one is being unfaithful so it is okay to do something you know will hurt him if that much is at stake for the two of you.

If not, think very carefully about whether you want to do something you know will hurt a good friend in order to date someone who may well be on the rebound. I don't know why this sort of thing feels like a betrayal, but it does, and you should take that seriously.
posted by Area Man at 2:22 PM on January 6, 2016 [9 favorites]


Be a good guy and walk away from it. I'm not sure you really want someone who jumped from a boyfriend to his best friend of a decade within one month of the break- least of which could be her playing out a reckless rebound.
posted by incolorinred at 2:32 PM on January 6, 2016 [4 favorites]


There's virtually zero chance you can have both. Choose.

FWIW there is no judgement from me here, and no odds-placing. My husband of 10 years was the boyfriend of a friend. We are obviously not friends any more.
posted by DarlingBri at 2:36 PM on January 6, 2016 [15 favorites]


Whatever you decide to do, don't do it behind your friend's back. My (former) best friend had a fling with a then-recent ex of mine and I didn't find out about it for a few months. The fact that he kept it from me made things worse, and our friendship didn't survive it. I didn't expect any kind of "honorable" behavior from my ex, but I did expect it from my best friend. I felt really betrayed by the whole thing.

All that said, if you value your friendship with this person you should stay far, far away from this potential mess.
posted by mudpuppie at 2:39 PM on January 6, 2016 [4 favorites]


Mostly I'm of the "there are plenty of fish in the sea, is this worth losing a good friend over?" camp. But I do have a pair of friends who got together about six months after the guy broke up with another girl they'd both been friends with. Pair of friends has now been married for more than a decade, so it seems ridiculous to say they shouldn't have dated. BUT it did torpedo both of their friendships with First Girlfriend. All this time later and that friendship never recovered. So if you feel strongly about this woman, go for it, but know that your friendship with her ex is likely toast unless he chooses to not hold a grudge.

(I'm very much of the "he doesn't own her and has no say in who she gets to date" school of thought, but while that is absolutely true it's probably not going to mitigate his hurt feelings for the near future.)
posted by MsMolly at 2:40 PM on January 6, 2016 [7 favorites]


This all depends on how much of a connection you feel whether or not it's truly worth it. None of us can know, that's why the answers all bounce between no and yes. I would trust your gut.

What is reasonable is that if you both feel such a strong connection, you cool it for a bit and you can see if it's real or just a rebound and you can talk to your friend. If it's a good connection, there's no reason why it has to be RIGHT THIS SECOND instead of in a month. Though I know how hard waiting is when you're really into someone...

The only clear thing is that you must talk to the friend if you do go forward. Do not let him hear about it some other way. That's hurtful, demeaning and puts your relationship in the light of skulking in the shadows.
posted by OnTheLastCastle at 2:56 PM on January 6, 2016 [1 favorite]


The situation you describe is fairly dramatic and the best way to not hurt anyone is to just walk away, because this doesn't end well 99.99999% of the time. And while you're walking away, you might want to do some thinking about why you want to be in such a dramatic situation. What you're doing is, well, pretty destructive to yourself, your friend, the woman, and your ties with and to one another. Why?

Like people said above, if this is going to work, it will work later. If you must, you can wait awhile until the dust has settled. Best of luck.
posted by sockermom at 3:05 PM on January 6, 2016 [3 favorites]


The smart thing to do would be to tell her "I really want to pursue this but if we do it this soon it will hurt my friend (YES IT WILL, IT ABSOLUTELY WILL), can we try again in six months?"

"What if she's not interested in six months?" Yeah, exactly.
posted by showbiz_liz at 3:14 PM on January 6, 2016 [34 favorites]


YMMV, but i've been in a somewhat similar situation.

Not that we actually dated either, we just started hanging out all the time. My friend was pretty hurt, and it almost ruined our friendship. A few months later the ex got pissed that i was still friends with him and quit talking to me basically entirely, even though she knew at the outset i wasn't just going to quit being his friend.

This is the sort of thing you do like a year later. Maybe even more, if you're going to do it at all.

And really really ask yourself if it's worth it. She, and to a lesser extent you(and i only say that because she was just in the relationship less than a month ago) are consciously or not, doing something kind of manipulative and hurtful/regenge-y here. Or at the very least, inconsiderate and tactless. You don't break up with/get dumped by someone and go date their friend of a decade a couple weeks later if you're a reasonable adult.

I'm really really not in to any kind of bro-code sort of stuff and i'm not saying that at all here. I'm just saying that the Average Reasonable Person would likely be upset if their friend did this to them, and they wouldn't be a whiny baby for feeling that way.

I just really really see this ending as it not working out, or her getting bored, or realizing she wanted to spite him more than anything and leaving... and then you have no partner and no friend.

A REALLY good old friend of mine, like since childhood, did this to me once. And my ex convinced him not to tell me(she, somewhat misguidedly but with good intentions didn't want to hurt my feelings, and i believed her years later because she was just sort of bad at gauging that stuff). When i found out i actually wasn't that mad it happened, just sort of disappointed... but i was FURIOUS that he would go along with lying about it, and that he had roped a few other friends of mine into the lie or lie by omission as well. I only found out because a mutual friend told me in a really roundabout way since he thought it was sketchy.

So pretty much don't do this, if you do it be open about it, run if she doesn't want to be, be prepared to ruin your friendship, and don't expect it to work out.

On preview, what showbiz_liz said is super concise and on point. What reason is there not to wait? Even if she hadn't broken up with your friend, i'm one of those people who thinks it's just unhealthy to go straight from relationship to relationship like that with no breaks... And i have many cohorts who finally stopped doing that and only then realized how little breathing room it had given them and how much drama had flown by.
posted by emptythought at 3:24 PM on January 6, 2016 [3 favorites]


Speaking from my own very naive younger self's experience, think carefully about whether you want to ruin your relationship with your friend. Because even if everyone involved is super mature about this, it will 100% put a lot of distance between you and your friend. And one month-post-breakup is not a time when anyone is known for being particularly mature, you know?

Also -- in all likelihood, you will end up being a rebound relationship for this woman, even if she's not doing it intentionally. Given that, I think it is especially not worth it to risk a decade-long relationship with a close friend.

As others have said, if it is truly meant to be with this woman, and not a mix of lust-confusion-heartbreak-rebound-etc., things could still work out at some point a year or two from now, when the dust has settled and both your friend and the woman have both fully emotionally moved on from their breakup.
posted by rainbowbrite at 3:45 PM on January 6, 2016 [1 favorite]


This is a situation that happened to me! (Though I started dating my ex's friend several months after we broke up, it has to be said.)

Things that helped the situation that are outside your immediate control:

- I was the dumped, and my ex did the dumping. Which made things simpler in terms of allegations of cheating, "you dumped me to get with him", and him having any sort of moral high ground to judge who I dated after he broke up with me.

- My ex and I were never exclusive and the relationship wasn't all that serious.

- As I said, we waited a good long time.

- Once we started dating, it became clear that this new relationship was A Thing and not me trying to get back at my ex or a rebound or anything like that.

Things that we specifically did that helped the situation:

- My current boyfriend asked my ex (again, well after we broke up) if it was OK, before anything was actually going on.

- When current guy asked me out, I laid everything out and told him straight up what I wanted from the situation. I was basically like, "You know I dated X, but also here are extenuating circumstances Y that you probably don't know about, all of which means what I'm looking for right now is Z. We can't date if you're not on board with all of this."

- Per all of the above, all three of us are mature grownups who can be trusted to say what we mean and mean what we say. Zero drama.

- There were rumors in our social circle that we were dating before we, ourselves, realized we were dating. I think it helped that my ex was able to see an organic situation developing over time rather than some kind of collusion or betrayal or anything like that.

- Pretty much as soon as we decided to be In A Relationship, we told my ex together. We did this before telling anyone else about it. Though, as I said, from what I now understand, we ourselves were the last to know.

To be honest, my guy and I just announced to our general social circle that we're moving in together, and my ex seemed kind of awkward about it. So I think even under the ideal circumstances, sometimes not everything comes together perfectly. But if all three of you are the type of people who can live with that, I think that this could be OK.

Two more bits of advice:

- I hate Woody Allen, but I'm on board with the idea that "the heart wants what it wants." If this is meant to be, it will work out. Even if that means it's not always logical or socially ideal. I previously dated *another* friend of this same ex (ugh I know), and the guy was super cagey about offending my ex, and honestly that should have been a red flag that it was not going to work out. With my current guy, all my concerns were met with, "who cares, I want to be with you."

- If any of the three of you is prone to drama, I would drop this and understand that it's just not possible to find happiness with this type of arrangement.
posted by Sara C. at 4:16 PM on January 6, 2016 [1 favorite]


This is a mess no matter how you go about it, if you pursue this right now. A couple-few years down the road, maybe - but right now, or even in the next few months, or even longer, if you spend time together right now, you will be considered a factor in their break-up.

Is losing the friendship worth it? Is the fact that you'd be rebound for her worth it?

This isn't a common situation, at least for people with some decency and common sense who want quality relationships.
posted by stormyteal at 4:17 PM on January 6, 2016 [1 favorite]


The only way this will work out with minimal damage is if you don't pursue this relationship.

If you believe this woman will be the love of your life and are willing to hurt the other person / give up that friendship, then that's a bridge you'll have to cross knowing there's collateral damage.
posted by raw sugar at 4:28 PM on January 6, 2016


Years ago a relationship of mine ended on amicable terms.

Not long after he and a once-close friend of mine started dating. Had I known, I would have effusively congratulated them, told them they were a terrific match, and wished them well. (They eventually married.)

But I didn't know. One lied, one avoided me. I was hurt. Then, when I eventually found out, I was disgusted with them for assuming I would be some sort of odd jerk about it, and disgusted that skulking around and so on seemed like a better option than being nice to me. We were never friends again.

For what that's worth, anyway...
posted by kmennie at 4:47 PM on January 6, 2016


Friendships of a decade-plus are precious and rare; nascent romantic relationships fairly common. But if you have other good friends and/or a hard time finding someone to date, maybe these odds are worth playing.

Tell your friend, though. He's going to find out and feel how he feels. Might as well spare him your lies of omission.
posted by Scram at 5:34 PM on January 6, 2016 [2 favorites]


This will pretty much end the friendship, and who knows if the relationship will last? Unless she's the future mother of your children and has a glittery hoo-ha, I don't think it's worth the risk. If you must pursue her, it'll be over with him for sure if you do it now. It may or may not be if you wait about it.
posted by jenfullmoon at 6:11 PM on January 6, 2016 [1 favorite]


Unless your friend and her had a super-amicable breakup and are still friends and hang out and such, you're basically proposing a situation where you either have to keep your girlfriend and your friend separate or force your friend to hang out with his ex.

That to me is the logical reason to be upset when a friend dates an ex, not because you have some sort of ownership but because you're creating a situation where you basically force your friend to be distant from you to avoid being hurt.
posted by thefoxgod at 7:13 PM on January 6, 2016 [1 favorite]


Isn't it interesting what a wide range of responses there are here?

I think this really comes down to the three of you -- each of your character, personalities, and motivations. Some of that is known, and some probably unknown.

In reading your question a second time, two things jump out at me: your clear sense that you're hurting him, and that you'd consider not dating her. It seems to me that if that's truly an option, then you might not be feeling quite the connection that would make it worth it. But maybe you are, and you just like to take things at a moderate pace. I'm not judging or placing bets here. I have found that feeling like a certain path would be betraying someone or something is a pretty strong and useful indicator of which way (not) to go. That said, maybe you'd feel just as strongly that by not dating her you'd be betraying her and your potential future together.
posted by salvia at 7:15 PM on January 6, 2016 [1 favorite]


I don't think you should ask your friend if he's okay with it. That puts him in an impossible position: either he has to be the bad man who stood in the way of your happiness, or he has to give his blessing to something that hurts him. You already know he won't be okay with it. The question is, which do you value more, his friendship or the potential relationship with his ex?
posted by intensitymultiply at 9:58 PM on January 6, 2016 [5 favorites]


I get on super well with my ex, amazingly well in fact. I thought I'd be okay with him dating a friend of mine and it was none of my business, but I was really not okay at all. The pillow talk aspect made me feel vulnerable and exposed. The idea that my friend now knew my former partner's sexual story and also needed my hand-holding in a relationship she was now having with my ex: Bleuuurgggh. Fortunately, and predictably, it ended quickly. I haven't been able to retain the same level of friendship with my friend.

He then went on to date a gal who had just broken up with his long time buddy [Perth is small ok?]. She was clearly on the rebound and that relationship lasted a few weeks at most. He was accused of being a predator, waiting for the former friends' relationship to fail. The friendship was lost, and not because either person was an asshole. These situations are fraught.

I think some people deal with the end of their relationships by clinging a bit to that world of the ex, the familiar, the easy. We've all probably been there at some point - the nice best friend of the boyfriend, then huzzah, suddenly he's the One. The triumph that a guy of your old guy's world likes you and the romantic cluster of stupid thoughts about being well known by this person as a shortcut to intimacy. I just don't think it's a healthy thing to do, and the short duration of time that's elapsed is a Big Red Flag to getting yourself hurt, and abandoned by two people you used to know well.

Boundaries, man. Put up some boundaries.
posted by honey-barbara at 10:47 PM on January 6, 2016 [9 favorites]


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