Breaking up my friend's relationship. How?

August 30, 2008 7:26 AM

I have a friend ("Rob") who has a girlfriend ("Emma"). This is a question about how Rob can break up with Emma and how (and if) I can help him do this.

Normally this would be none of my damn business and I wouldn't get involved. But Rob has wanted to break-up with Emma for at least the last year. He's set himself several deadlines to do so, all of which have made a whirring sound as they flew by. I've been supportive. I've encouraged him to go through with it. But he hasn't. It's a ridiculous situation and I'm out of ideas.

I'm not going to go into too much detail. Rob and Emma got together a couple of years ago. Rob's previous relationship was long-distance and ended very badly. She was very controlling and Rob seemed to be constantly walking on egg-shells to protect her oh-so-delicate feelings. She broke up with him in a rather evil and duplicitous way. Emma's a vast improvement on this, but Rob still seems to do the same kind of thing, though to a lesser extent.

There are various points of conflict between them, but nothing very serious. There's no big reason for them to break-up. The problem is, Rob just finds the whole relationship very dull. He likes her and they get on well together, but that's about it. He seems to be completely bored by the whole thing.

Since he first realised he wanted out of the relationship, he's come up with every possible excuse for not doing so: Too close to her brithday; too close to Christmas; they're going on holiday; she's having a tough time at work. Occasionally he'll find a suitable time and set himself a deadline to break up with her. But something inevitably comes up. Then he talks himself back into thinking the relationship is what he wants, which lasts a couple of weeks, and he finds himself back in the same situation. Recently he managed to get to the point where he was making the phone call to have the break-up conversation, but he couldn't say the words.

Emma has no idea how he feels, although all his friends do, which makes it kind of weird when she's around. He feels bad about this and everything else, which doesn't seem to help. He worries that he's doing the same thing to her that his ex did to him.

As a friend, it's frustrating to watch him waste years of his life on these pointless and screwed-up relationships. Obviously I can't control him or his life, but sitting around saying "I know you can do it this time!" doesn't seem to be doing much good. Is there anything I can do to help him get over this? If you were ever in Rob's position, what helped you finally make the break? I'm assuming that waiting for the next time the three of us are out together and saying "Oh, and did you know that Rob wants to break up with you?" will have terrible consequences for all involved, but hey, I'm open to suggestion.

(Oh, and everyone involved is in their mid-twenties).

posted by xchmp to human relations (44 comments total)

It's a ridiculous situation and I'm out of ideas.

Has Rob specifically asked for your help? If not, let it go and just be supportive.

If he has, based on this (...he was making the phone call to have the break-up conversation, but he couldn't say the words.), have him write a letter and deliver it to her when they're alone together. That way she is at least given the dignity of being able to react to him in person.

But really? It sounds like Rob has some major issues that he needs to sort out with professional help. Encourage him to seek it.
posted by Brandon Blatcher at 7:39 AM on August 30, 2008

Alright, one thing to know is if he wants to be relatively nice about it or if the only thing important is to get out.

If he wants to be nice, then just have him explain to her that he doesn't see the relationship going anywhere and things should end.

If he just wants out, then he can either be really blunt or he can just start acting like an ass and get her to break up with him.

But the real problem here seems to be his lack of motivation. Yes, it sucks if you get broken up with close to a birthday or Christmas or something like that. But he needs to stop thinking about that. It's going to suck when ever he breaks up with you.

As twisted/wrong as this sounds, it might take you rewarding him for breaking up with her. Get him tickets for something he wants to go to that he can't have unless he breaks up with her. Take him out to eat to celebrate.

If Rob agrees with it, bringing up the subject might not be such a bad idea. It would throw it out there in a way that can't be ignored. Last resort though.

But as Brandon Blatcher said above me, if he hasn't asked for your help don't try. At least beyond telling him "figure out what you want to do and actually do it."
posted by theichibun at 7:44 AM on August 30, 2008

People who don't do things that they say they want to do don't want to do them.
posted by Ironmouth at 7:49 AM on August 30, 2008 [33 favorites]

If Rob really wanted to break up with Emma he would have done it already.

When I was 17 I had this friend that had a controlling mother and being my 17-year-old self I would agree with my friend how horrible her mother was and encourage my friend to move out. My friend wasn't looking for advice to move out or break away. She was looking for a shoulder to cry on. I cringe at my behavior and advice. Advice wasn't needed. Empathy was.

Rob is your friend and he shares his problems with you. This is great. This is what friends are for. It's not your role to encourage him to break up with Emma (unless there is abuse). Even if he expresses that he wishes to break up with Emma you should not encourage him to end his relationship. You can say" hey pal, that sounds rough", but you shouldn't be rooting him on to break up with his girlfriend. That's too much involvement. It could end badly. Rob could resent you for rooting him on.

Rob looks like a fool for complaining how dull Emma is to all of his friends and remaining with her. Maybe you could advise him to stop complaining about Emma because it makes him look dull and isn't fair to Emma.
posted by Fairchild at 7:59 AM on August 30, 2008 [8 favorites]

I honestly don't think there's anything you can do to help your friend break up with his gal. The only way I can imagine is to tell her everything you've told us...but you'd be a jerk for doing that and I'm guessing Rob would then begin talking to everyone about how he wants to be away from YOU. You are a very good friend to be trying to help, but this is really Rob's own personal problem. Getting involved with a friend's personal problem such as the one you're stepping into is just going to require all sorts more of time and free rent in your brain. Reassess your boundaries and then start spending more time on yourself. Set a healthy example for Rob so he can see how happy a person can be when they decide to live an honest life. Doing it like this really could serve as a healthy cognitive intervention for Rob. Rob kind of sounds like a butthead if he's talking behind his girlfriend's back for a year (how exhausting that must be for you!) about wanting to break up with her. Chances are, she feels just as bad about him as he says he feels about her. Rob sounds like a pretty ineffective guy who would do well to grow a pair. It is a good and great thing to intend to help a friend but there is a point in a person's life (in the 20's is a good time for this lesson) when they have to take responsibility for their own happiness and not dump on their friends about it.
posted by mamaraks at 8:08 AM on August 30, 2008

Sounds like maybe your friend is drawn to the dramatic relationships, knows its not the best trait and wants to try something less full of turmoil, but finds it "boring". Theres a struggle between the kind of relationship he feels like he 'should' have and not knowing what to do when there isn't insane drama, maybe?

In any case, if he really wanted to he wouldve by now, and stay out of it, as no good will come from you meddling. If it bugs you to hear him complain about wanting to get out of it, tell him to stop complaining to you.
posted by softlord at 8:11 AM on August 30, 2008

Rob is being a complete and total asshole. He's being an asshole, apparently, because he doesn't seem to be able to parse the difference between "being nice" and "being kind." Being nice means stroking somebody, feeding them candy, smiling and uttering warm, fuzzy, meaningless phrases. Rob is being nice. Being kind means having someone's best interest in mind and acting in a way that serves that interest, even if it's tough. I've seen people shoot horses out of kindness; it wasn't nice, but it had to be done.

Rob should man up. He's barreling down the road that leads to the destruction of Emma's life. She, by all accounts, seems to be someone who'd actually like to get on with her life and be with someone who actually gives a damn, and Rob is afraid of letting her do that because it might ruin her day.

Tell Rob that he's being a tool, and that, if he thinks he's saving her feelings, he's full of it. He's being an ass to her. She clearly wants to be in the relationship. Does he? He needs to make a decision and stick with it; otherwise, he's just "being nice."
posted by koeselitz at 8:14 AM on August 30, 2008 [17 favorites]

xchmp: I'm assuming that waiting for the next time the three of us are out together and saying "Oh, and did you know that Rob wants to break up with you?" will have terrible consequences for all involved, but hey, I'm open to suggestion.

Come on. Can't you see where that would lead? You're engaging in wishful thinking when you say that would have 'terrible consequences' - just the opposite.

You'd say that, and Rob and Emma would go off and have a conversation where Rob would attempt valiantly, and probably successfully, to prove to Emma that he doesn't want to break up with her, that he loves her very much, that you were just being a jerk, or you were drunk or something, and how could Emma think that? Of course Rob doesn't want to break up with her.

See? Unless he's the one to do it, he's not going to tell her he wants to break up with her. If he's been preserving the status quo for years, he's not going to rock the boat now unless he really steps out and chooses to.
posted by koeselitz at 8:19 AM on August 30, 2008

People have to run their own lives. As hard as it can be to sit back and do nothing when it seems like there must be something you can do to prod someone in the right direction, often that is your best option.

And I'd tell Rob I can't listen to him discuss this issue anymore. He knows what he has to do and it isn't a good use of time to keep hashing it over and over.
posted by orange swan at 8:22 AM on August 30, 2008 [3 favorites]

Please tell her-

1. You'll be doing a favor to Rob, by helping him break up.

2. You'll be doing Emma a even bigger favor by helping her move away from such a whiny user.
posted by francesca too at 8:24 AM on August 30, 2008

If he brings it up, ask him how you can help. That's it. Maybe you hear only the negatives because he needs a sounding board. Maybe he doesn't know what he wants. If you take action, it's likely to backfire.

You could suggest a good therapist, I suppose.
posted by theora55 at 8:25 AM on August 30, 2008

To answer the question:
Sleep with Emma, tell Rob.
posted by whoda at 8:36 AM on August 30, 2008 [5 favorites]

Do not exclude the possibility that he complains about the relationship out of defensiveness and a fear that you and his other friends don't approve. On that scenario, he may in fact be reasonably content, but anxious about how the relationship is perceived.

At the same time, as to this sentiment:

People who don't do things that they say they want to do don't want to do them.

This is a good generalization, and has a sloganish quality tailor-made to this kind of setting. But it's simply wrong as an absolute, unless you qualify it heavily. People behaving this way certainly don't want SUFFICIENTLY do them; but they may want to do them, and would do them, but for inertia, fear of short term costs, misplaced concern for the other person (who would be better off knowing), etc. So it's entirely fair to inquire as to why your friend hesitates, while bearing in mind that he is in fact hesitating.

FWIW, I do think you should butt out, while trying to avoid driving his opinion one way or the other about the merits of the relationship . . . Or at least be explicit about your own opinion with him, if you must, while leaving to him the heavy lifting.
posted by Clyde Mnestra at 8:38 AM on August 30, 2008 [2 favorites]

Telling Emma that Rob wants to break up with her will certainly end a relationship.

The relationship between you and Rob.

Ask Rob if he wants help from you, and if so, what kind of help. Don't be Captain Save-A-Schmo.
posted by Sidhedevil at 8:59 AM on August 30, 2008

Good advice here.

To clarify a couple of points: I'm about as certain as I can be that Rob genuinely does want to break up with her. He doesn't complain about Emma to his friends, just about the fact that he's in a relationship with her. He tends to initiate the serious talks we have about this and, as long as I didn't go behind his back I think he'd appreciate any advice, insight or suggestions I could give. We're pretty close.
posted by xchmp at 9:04 AM on August 30, 2008

The fact that you and everybody and their brother knows that he at least says he doesn't want to be with her, and yet she doesn't know (perhaps) is beyond cruel to her. What bad thing has this woman done to him (or to you for that matter) to be treated this way, like a child who isn't allowed to make their own decisions and has to be supervised/managed/controlled by being kept in the dark about an essential part of her life? Do you all enjoy trying to humiliate this woman because basically that's what you're doing. She is pretty much being played just for being dull and boring (from the boyfriend's POV, anyway; maybe he's just too lazy to put in some needed effort into the relationship or get out and find someone who isn't dull and boring to him).

On the one hand I think you should MYOB but your pal has pretty much made that impossible if you're at the point where you're asking a bunch of unknown people on the internet what to do. I think first and foremost this woman needs to know the truth, as soon as possible. How about e-mailing this thread to him? At the very least it might shock him to see how the situation looks in writing, how various uninvolved people interpret it, and how his behavior has affected you, his so-called friend. That awareness might finally motivate him to do the right thing by this woman. And if he doesn't do the right thing you could set up an anonymous e-mail account and "accidentally" email it to her too. Sometimes situations don't get resolved until a crisis is created around it. Just be prepared to handle the fall out.
posted by fuse theorem at 9:04 AM on August 30, 2008 [2 favorites]

He tends to initiate the serious talks we have about this and, as long as I didn't go behind his back I think he'd appreciate any advice, insight or suggestions I could give. We're pretty close.

Well, there's never a right and easy time to break up with someone. Unless you're getting beat over the head or you walk in on your partner shagging someone else. It's like having a baby or getting married. You just have to do it.

There is a feeling that overcomes a person when they know they want to make a break. Staying is not an option. The feeling is I'm getting the hell out of here. I don't want to be with this person. It's unfortunate that her dog just died and Christmas is next week but I must get out of this relationship. Nothing can make me stay. Rob is not at this point. He's still planning holidays with Emma. He's not ready to break it off. Be a supportive friend. Listen, but don't help him plan how he will execute the operation. That's his deal. Don't make it your business. It's tacky.

I have to wonder, what is in it for you? Why are you so intent on offering solutions to Rob to break it off? Is it making your life any harder that he is with Emma? Good luck.
posted by Fairchild at 9:25 AM on August 30, 2008

I have to wonder, what is in it for you? Why are you so intent on offering solutions to Rob to break it off? Is it making your life any harder that he is with Emma? Good luck.

I don't particularly care whether he stays with her or not. But he's a very good friend and this constant wavering between wanting to break-up with her and pretending everything's fine is just making him unhappy. If he could decide to stay with her and make the relationship work, then I'd be fine with that. But it doesn't look like that's going to happen.

And if they're going to break up, then it seems like it would be better for both him and Emma if it was before they got any more involved. At the moment they're not even living together (actually they both still live with their parents), so they're not all that entangled in each other's lives.
posted by xchmp at 9:34 AM on August 30, 2008

Since he first realised he wanted out of the relationship, he's come up with every possible excuse for not doing so

If he actually wanted out of the relationship, he would actually end it. His coming up with "every possible excuse for not doing so" is his way of letting you know that he doesn't actually want to end it.

It may be that the relationship is terrible and makes him unhappy and is a bad idea to continue. But that's his business, and if he decides he is serious about ending it and needs your help he will ask you.

Absent indications of abuse or blackmail or something unsavory like that, you need to mind your own business and let your friend figure this out on his own. Be supportive, show through your own life how good real relationships can be, but don't interfere where you are not wanted.
posted by Forktine at 9:38 AM on August 30, 2008 [1 favorite]

I don't particularly care whether he stays with her or not. But he's a very good friend and this constant wavering between wanting to break-up with her and pretending everything's fine is just making him unhappy.

Then he needs to learn from his own unhappiness. You can't (and shouldn't) expend your own energy trying to keep friends from the difficult emotional consequences of their own decisions. Or indecisions.
posted by Sidhedevil at 9:41 AM on August 30, 2008

he will continue to find himself in situations like this until he learns how to extricate himself. so "helping" him, really wouldn't be helping him - he'd just end up in the same place the next time.

it's a lesson he has to learn on his own, unfortunately. if he's really that unhappy, he'll figure it out for himself.
posted by wayward vagabond at 9:45 AM on August 30, 2008

Your friend is not being a gentleman, good friend or lover. Rob tells you ALL in his social circle that he is not happy in the relationship with Sara thus, creating discomfort for you all when you see her; Sara is viewed with a combination of pity and contempt, after all, she is considered dull and boring - not worthy of your or his care (you are on his side on this, not hers) and what kind of person claiming kindness and affection badmouths a person like this over an extended period of time? Definitely not someone who cares.

Your friend is being massively passive aggressive for many reasons. It is not good for you, his social circle, and definitely not for her. After all, she is with an emotionally deceptive and socially cruel person. Is what he is doing something a kin to extending the oh so sweet pain of impending drama? Does he savor pulling the scabbed up bandage slooowwwllllyy 'cause it is a longer tingle factor? Let us fast forward in time and think what you are going to do, because of his relationship inertia, marries Emma? What role do you plan to have at that point?

Take the advice from previous askMefi threads, which was not to get involved in a boy girl fight. This is your friend's choice in every way. Do not become the scapegoat for drama. Do not fall into passive aggressive traps.
posted by jadepearl at 9:46 AM on August 30, 2008 [1 favorite]

There is not a good way to break up with someone and the timing will always be wrong. This cannot hold your friend back.

Obviously, the ‘best’ way would be to be as straightforward as possible with her but he knows this and hasn’t done it. If he wants to be more of an ass, he can do the same thing he would do if he wanted to get rid of an annoying friend: don’t talk to her for a week or two. Ignore her calls, texts, whatever. When he does talk to her (after waiting at least a week), offer a weak excuse about being too ‘busy’ and then they can make plans to get coffee or dinner or whatever. Lather, rise, repeat for a month or two and then sit her down and tell her “you know….I’m really kinda busy lately with other things in my life and I’m not sure how this relationship fits in with all of that.”

That won’t really work if they live together, have a load of mutual friends, etc but any change in their routine would hopefully prompt her to ask him if anything is up and he should have the stones to tell her that yes, something big is up.
posted by Diskeater at 9:52 AM on August 30, 2008

…but I agree that unless you’ve specifically been asked to help him out, you should mind your own damn business unless the relationship is really, truly harmful to either of them (think emotional / physical abuse and it doesn’t sound like that’s going on here). You’re his friend! Your job is to take him out for a beer and let him rant about his life.
posted by Diskeater at 9:55 AM on August 30, 2008

I have been given this advice and have reminded myself of this on a couple of occasions:

If you're going to stay with the person stop wallowing in your own self-pity. If you're not going to break up with the person make efforts to make it more meaningful and exciting, instead of dwelling on the negative and creating more misery.



The problem is, Rob just finds the whole relationship very dull. He likes her and they get on well together, but that's about it. He seems to be completely bored by the whole thing.

Hmm. This brings back memories of how I used to think. Boring people get bored. Rob makes his own life. If she's a genuine stick in the mud why isn't he gone? Rob is scared. Rob is probably boring and doesn't want to be. He probably enjoys the relationship most of the time but wants to be someone he is not and blames Emma.
posted by Fairchild at 9:55 AM on August 30, 2008 [5 favorites]

It's good to want to help a friend, but I think it's more useful to consider it this way: Breaking up with Emma, on his own and in his own way, is Rob's prerequisite for getting on with the rest of his life and finding a new relationship. Shielding him from or blunting the responsibility and the lessons he needs to learn from it only do him more harm. The intervening pain, suffering, and inconvenience are part of life and are necessary for Rob to guide his future decisions. So, in a way, it's like you're asking for how you can get away with not vaccinating your child for common deadly diseases.
posted by troybob at 10:02 AM on August 30, 2008

People are in the relationships they want to be in.

Accepting this fact has made me a much, much less frustrated person.
posted by LittleMissCranky at 10:21 AM on August 30, 2008

Rob likes drama. He doesn't actually want to break away, and is being crappy to Emma so he can be a victim by blaming her for the relationship troubles. He's bored because Emma does not provide the drama he seeks, and while he resents her for being stable, he'd rather use you for his source of OMG!!! then find a girlfriend who was actually loopy enough to keep him entertained.
posted by Phalene at 10:23 AM on August 30, 2008 [1 favorite]

You know what sucks? Breaking up on your birthday.

You know what is worse? Having some guy waste a year of your life because he can't be a man and break up. You should kick your friend in the ass and tell him he needs to break up with her today.
posted by munchingzombie at 10:39 AM on August 30, 2008

If he actually wanted out of the relationship, he would actually end it.

People are in the relationships they want to be in.

*Again* with this stuff. "If he actually wanted out of the Army, he'd go AWOL." "People have the operating system they want to have."

These things are certainly true, at some level, but wish away all the frictions. Relationship threads at AskMe broker a twisted hybrid of microeconomics and fatalism, where everything sorts itself out according to an unwavering inner logic -- perish the transaction costs or informational failures -- or, at the very least, can't be altered.

While we're at it, why don't we subscribe to the idea that people only follow the advice that they already have?
posted by Clyde Mnestra at 10:44 AM on August 30, 2008 [2 favorites]

In my late twenties, my best friend at the time was in Rob's position. He was bored, he wanted out, and he couldn't bring himself to be straight with his Emma about it. He could certainly make it clear to everyone else, though, which was none too comfortable. I tried a bunch of things: I supported him; I admonished him with advice like the advice that Fairchild mentions; I washed my hands of it and refused to let him whine about it at me until he did something. The only thing that I saw that actually changed his behavior was meeting a woman he wanted to date instead of Emma-equivalent, at which point he dropped her flat.

But the real moral of my story is, don't you get too attached to Rob. Eventually, my friend pulled the same stunt on me that he did on his girlfriend. He decided that life was too boring, and that I was too boring to fit into his exciting new life fantasies. So he treated me rudely and ran down my reputation among our mutual friends until I gave up and went away. And I wasn't the only friend on which he pulled this nonsense, nor was I the one who got the worst of it.

It's too bad -- I liked him a lot. I won't deny that he had many virtues. But integrity wasn't one of them. In retrospect, I should have seen something about his character from the way he treated her. I think jadepearl would call him, too, emotionally deceptive and socially cruel, and she'd be right. My conclusion: emotional cowards don't make very good friends over the long run. For that reason alone, I would resist getting sucked into this Rob-Emma business.
posted by sculpin at 10:44 AM on August 30, 2008 [13 favorites]

I agree - if Rob truly wanted to break up with Emma, he would have.

I was in the same situation as you for a long time. I have a very close male friend who would whine and complain to me about his girlfriend but never break up with her, even though things were "terrible". He would remain in these relationships for years at a time. This pattern went on for years and still continues today (he's 37 y/o). Each girl would eventually leave him because he mentally and emotionally just "checked out" of each relationship without telling them.

As a friend, it was annoying and frustrating. As a woman, I was appalled and angered by his behavior. I finally got to the point where I wouldn't talk to him about his relationships anymore, for the sake of my sanity. I support him as a friend when things end, but beyond that, I've chosen to make this topic "off-limits" for us. Things may change if he changes his behavior, but for now, this is the way things need to be.

You can't make someone do what they don't want to do. He's choosing to stay in this relationship. Not making a decision is still making a decision. If he wants to get out, he will. Right now it sounds like he's looking for attention and drama. Give him some tough love and tell him to man up by either breaking up with her or stop complaining about her.
posted by Nutritionista at 10:49 AM on August 30, 2008 [1 favorite]

sculpin's got it. Your "friend" Rob is, as many have noted, being a passive-aggressive manipulative jerk with respect to his relationship with Emma. Your (and to a lesser extent, your other friends) involvement makes you complicit.

The only break-up you need to be involved in is between you and Rob. It's not your duty to be supportive or empathetic toward his, frankly, shitty behavior; it's your duty to make this clear to him by not being around him until he can stop involving you in his drama. He clearly doesn't value his relationship with Emma. If he cares at all about his relationship with you, he'll do something about it.
posted by mkultra at 11:37 AM on August 30, 2008 [1 favorite]

You need to tell Rob to quit being a wimp and shit or get off the pot, and not to talk to you about his relationships until he does.

On preview, what Nutritionista said.
posted by rhizome at 11:54 AM on August 30, 2008

Thanks for all the advice. I figure next time he brings it up, I'll say something along the lines of:

You say you want to break up with her, but you've been saying that for the last year, so I have to question how sincere you are about it. I wonder if you really find Emma as dull as you seem to, or if you're just worried that you're settling into this boring life. So break up with her or don't, just make a decision and go through with it. Maybe you just need to fully engage in the relationship you're in before you can actually start to feel that it's the right thing for you. Or maybe you really do have this terrible problem telling her you want to break-up. Either way, until you're done, I don't want to talk about it any more.

We both know that, if you are going to break up with Emma, you're being a complete asshole by delaying it this long. You probably feel like you're being kind to her. But you're not. It may suck to be broken-up with, but it sucks more to have someone waste a year of your life. So if you're going to do it, do it now.

But anyway, I don't want to be a part of it anymore. It's obvious that there's nothing more I can do or say that's going to make a difference. It's up to you to do what you need to do in your own life and if you can't do that, maybe you need to talk to a therapist. If you truly don't want to be with Emma, then I'm not going to watch as you throw away years of both your lives. And if you do want to be with her, well, get on with it and stop whining.

If you have a genuine problem you want to talk about then you know I'm happy to listen. But what you're doing here isn't fair to Emma, your friends, or yourself.

Any further advice is definitely appreciated and if you think I should say anything else, go for it.
posted by xchmp at 12:04 PM on August 30, 2008 [5 favorites]

There is a possibility that your friend will become defensive with calling him an asshole and suggesting he see a therapist.

I would cut it way down and only say this:

It may suck to be broken-up with, but it sucks more to have someone waste a year of your life. There's nothing more I can do or say that's going to make a difference. It's up to you to do what you need to do in your own life.

Only say the above if he broaches the topic. Keep it short with a friendly tone. If he brings it up again after you have spoken with him change the subject.

Clyde Mnestra has a very good point about the possibility of Rob complaining about the relationship out fear you won't approve. You may want to make him feel easy about staying in the relationship. Say something positive about Emma and the relationship and notice how Rob responds. He may not want to leave and is seeking approval from friends.

Good luck.
posted by Fairchild at 12:58 PM on August 30, 2008

"Rob, you are my very good friend, but I don't want to hear another word about you and Emma. There is nothing left to discuss, you've been complaining about the same thing for months and months and I'm tired of it. It's driving me so crazy I'm trying to think of ways to break you up, which is very un-cool. If you want to keep being my friend you need to either do something about the situation with Emma or never talk to me about it. Understand? Good. Now let's go get a beer."

This tactic has saved a relationship with a friend who was stuck in a situation they were in control of but couldn't stop complaining about. He eventually took some definitive action when he saw his (in)action was bothering the hell out of everyone he knew.

Alternately get the card of a good therapist and give it to him next time he brings it up becsue he could use some trained help with this. This whole situation goes above and beyond what a friend should have to do for a friend.
posted by Ookseer at 1:44 PM on August 30, 2008 [1 favorite]

Rob likes drama. [...] He's bored because Emma does not provide the drama he seeks, and while he resents her for being stable, he'd rather use you for his source of OMG!!! then find a girlfriend who was actually loopy enough to keep him entertained.

Next time he talks about breaking up with Emma but doesn't go through with it, punch him in the face as hard as you can.

When he accusingly says "what did you do that for?" tell him you're sick of listening to him running down this nice girl in public; you're angry he's doing such a crap job of holding up his end of the relationship; and you're tired of seeing your friend making himself less of a man by complaining about solvable problems but not showing the courage to solve them. Tell him that until he breaks up with Emma, any time you hear him talking about breaking up with Emma (even if it's with someone else and you aren't part of the conversation) you're going to punch him hard in the face.

It doesn't get much more dramatic than that... he gets the drama he wants, it helps Emma out, and you don't have to listen to him complaining any more. Everybody wins!
posted by Mike1024 at 4:05 PM on August 30, 2008 [1 favorite]

If he really wants to break up with her then maybe he can handle writing the letter... its still nice but not confrontational. If the feelings aren't mutual he needs to tell her so she can move on and find someone that will appreciate her obviously but I'm not sure what you can do about it. I normally would just be a supportive friend, he needs to decide for himself and it sound like he's confused and not entirely sure he wants to break it off. Also be careful as you never know when people might regret things and then your friendship may be damaged.
posted by CharlotteSarah at 4:26 PM on August 30, 2008

Hell, I ended a 5 year relationship ON OUR 5 YEAR ANNIVERSARY.

The best time to end a relationship is usually about 6 months before you actually do.

Sometimes longer.
posted by the bricabrac man at 5:32 PM on August 30, 2008

It's hard to end a relationship. But nobody can do it for anybody else.

Man up and butt out.

You get something from listening to these endless conversations about how much (his relationship with) Emma brings him down. If you didn't get something out of this situation you'd find a way to end or re-route those conversations, since you know he's not formulating a plan of action.

Figure out for yourself what space this fills in your life and straighten that out before you go straightening out your friends' lives. Trust me, each of us has plenty to work on that we don't need to spend time fixing other people. Those of you who have the time to seek out places to help might be better suited to offer it to people who clearly want it. If Rob had come to you and said, "I'm leaving Emma next weekend and want to get away for a few days to escape the fallout, got any suggestions?" I'd be thrilled to help. But from what you've presented, I'm not convinced he wants any more than a shoulder to cry on.
posted by bilabial at 5:55 PM on August 30, 2008

It's not easy to inflict pain on someone else.

Tell him to read How To Dump a Guy: A Coward's Manual, by Kate Fillion and Ellen Ladowsky.
posted by russilwvong at 7:37 AM on August 31, 2008

They're both in their mid-20s and living at home with their respective parents? This isn't a relationship. Sounds to me like Rob's just killing time with Emma until he grows up a bit, and that's not really your problem. Tell him you're sick of talking about it, the topic is boring to you, and then butt out.
posted by booknerd at 10:01 AM on September 1, 2008

I went out with someone who told his friends how awful being with me was and how he wanted to dump me and sleep with other women, but was worried 'something might happen to her', all the while telling me how great I was and how he just had trouble with relationships. Finding this out hurt a lot more than the break-up. A lot lot more. And one of the friends he told was a mutual friend who ended up in a very awkward position, resulting in her saying 'If you won't tell her, I will', and the loss of her friendship with him. Tell him to sort himself out. Please.
posted by mippy at 3:49 PM on September 4, 2008