My patience is running out!
December 9, 2009 7:32 AM   Subscribe

My close friend hates my boyfriend. Can this be reconciled?

Earlier this year, a close friend (who lives in a different city, I don't see him much, most conversation is online) expressed to me that he was interested in being more than friends. I declined, I have no feelings for him, and that was that...until I started seeing my now-boyfriend, about 7 months ago.

Friend has decided that he hates everything about Boyfriend. Everything about Boyfriend is terrible (despite the fact that they have a tremendous amount in common!), Friend makes passive-aggressive remarks about Boyfriend constantly to the point where I just stopped mentioning Boyfriend to Friend, but he still finds ways to make his displeasure known. Friend has left nasty comments on Boyfriend's blog.

Boyfriend is wonderful and patient with all of the drama Friend has thrown at us. Boyfriend is no trouble at all. Not breaking up with Boyfriend over this.

The question is, how should I handle this? What can I say to Friend to make him stop (or at least realize that he's destroying our friendship)? Every discussion we've had over this has ended in me apologizing to him! I don't even know how that happens...I'm not very good in arguments. I am extremely hesitant to cut out the friendship because, aside from this, we're very close. Friend has been there for me, we've been there for each other, through some extremely difficult times and some of my happiest memories have been with him. This seems like a silly reason to stop being friends, Friend would like Boyfriend if Friend would just give him a chance. Advice. Advice, please!

posted by anonymous to Human Relations (52 answers total) 2 users marked this as a favorite
Friend is jealous of Boyfriend. Until he gets over it there isn't much you can do.
posted by Vindaloo at 7:33 AM on December 9, 2009 [20 favorites]

Friend is jealous. Friend needs to get over himself. Please stop apologizing.

I think you have to draw the line and say, "You're not going to convince me to stop dating my boyfriend. So either stop trying, or I'm going to have to spend less time with you." Because it's going to poison your friendship.

Or just say, "I don't want to hear your opinions about boyfriend, so just keep them to yourself."

But be aware that friend is obviously still carrying a torch for you, and at some level probably resents you for not dating him instead of your boyfriend.
posted by musofire at 7:36 AM on December 9, 2009 [2 favorites]

Friend would like Boyfriend if Friend would just give him a chance.

No, he wouldn't, because Friend will never be able to deal with the fact that you are sleeping with Boyfriend and not Friend. The fact that you view them as having so much in common makes this worse, not better. Stop thinking that you will be able to surmount this difficulty.

The best you can do is to cut off this part of your life from Friend. You can have a rich relationship with Friend without the Boyfriend part ever entering into the equation, especially if this is a long-distance friendship. You've already stopped talking about Boyfriend, now ask him to stop bringing him up as well, and definitely to stop engaging Boyfriend, which means not to contact Boyfriend at all, including via comments on his blog.

If Friend can't stop doing this, then I don't think a true friendship is what is at stake here.
posted by grouse at 7:40 AM on December 9, 2009 [4 favorites]

"Look, man, you're being fucking psycho about this. I don't want to hear you making snide remarks about him anymore, I don't want to see your nasty comments on his blog, and if you can't let it drop, I'm not going to stay and listen."

Then, back it up. He makes a remark, you end the conversation. He leaves a snotty comment somewhere, you call him on it the next time he tries to talk to you, and then you end the conversation. It's not "ending the friendship", it's setting boundaries, and it's the only way he's going to get the message.

(You do realize he's not over you, right? And this is his passive-aggressive way to try to say he thinks you'd be better off with him? This isn't a very healthy friendship at the moment for that reason alone, and y'all might both be better off with a lot less contact until he gets over you.)
posted by restless_nomad at 7:41 AM on December 9, 2009 [30 favorites]

I think that if you're as close to Friend as you say you are, then you need to need to be upfront, honest and blunt with Friend.

"Knock it off. Now."

If Friend is as good a friend as you have stated, they will stop and allow you to be happy with Boyfriend.
If they don't, then they may not have been the friend you believed them to be.
You move on and be happy.
They move on and be happy.
posted by willmize at 7:42 AM on December 9, 2009

One of my best friends-friends for 22 years- married a guy that I was less than happy with. I was pretty irritated initially, told her I would not be at her wedding because I felt that she was making a big mistake (but I guess the difference was that, I told her that I love her and want her to be happy, but just didn't support the nuptials...she was ok with it). Her now-husband isn't all that terrible, still not really fond of him.

But, in my case, we're both girls with no romantic inclination towards each other. Friend still likes you. What would I do? Might not work for you, but I would tell him that he is destroying the friendship, reiterate that you don't have feelings for him, and tell him to suck it up and deal with it. Why are you apologizing to him?!? He should be apologizing to you! Just tell him point blank, or write him a note if you don't think that you can do it face-to-face. He needs to grow up and accept that you are not interested in him. His behavior clearly illustrates that he has not taken 'no' for an answer, and you may be coddling him like a 2 year-old that throws a tantrum when he doesn't get his way.

Good luck!
posted by bolognius maximus at 7:42 AM on December 9, 2009 [1 favorite]

Ditch your 'friend.'
posted by KokuRyu at 7:46 AM on December 9, 2009

Yeah, jealous. I know two dudes that should be the best of friends, but they're both into the same girl (who has a boyfriend) so they fucking haaaaate each other.
posted by electroboy at 7:49 AM on December 9, 2009 [1 favorite]

Friend makes passive-aggressive remarks about Boyfriend constantly

Friend has left nasty comments on Boyfriend's blog.

This is not ok behavior. And it is not the behavior of a friend. It's not ok for him to trash your boyfriend just because he (your friend) has feelings for you and is jealous of your boyfriend.

This seems like a silly reason to stop being friends

Actually, it sounds to me like a great reason to stop being friends--or at least to take a break. If I were you, I'd give him an ultimatum: "If you don't stop talking about my boyfriend this way, I can't continue talking to you."--and then stick to it. It's ok for your friend not to like your boyfriend, but it's rude and disrespectful for him to make these comments about him to you. And to post nasty comments on your boyfriend's blog? That's super weird and creepy.
posted by Meg_Murry at 7:51 AM on December 9, 2009 [3 favorites]

Dump the friend. Because he's always been a bf-in-waiting in his own mind. In regards to being friends with people who have a sexual interest in you which is not reciprocated, I think it is always important to examine their motives (and one's own motives) in such a situation. This goes for men and women, women and men, men and men, women and women, straight woman and gay man, gay man and straight woman, straight man and gay man, gay man and straight man.
posted by Ironmouth at 8:09 AM on December 9, 2009 [4 favorites]

Yeah; he's jealous. Shut him down.

Since most of your conversations are online, this is easy. Next time he trashes your boyfriend, abruptly end the conversation with a "Whelp, gotta go." Then log off.

He'll get the hint.
posted by LuckySeven~ at 8:11 AM on December 9, 2009

aside from this, we're very close. Friend has been there for me, we've been there for each other,

He has been there for you because he thought there was a chance you may change your mind and date him. Now that theres much less of him breaking free of the friend-zone, his 'friendliness' has faded. It's commonest thing in the world. No need to cut all ties, just keep more of a distance. If he asks why, explain that it is because he is not being very cool. Cite examples.
posted by ElmerFishpaw at 8:12 AM on December 9, 2009 [8 favorites]

Your friend is hoping that by badmouthing your boyfriend you'll suddenly realize that your boyfriend is completely wrong for you. Your friend is then hoping you will finally see him the way he sees you and fall madly in love with him.

Your friend needs to learn that life isn't a romantic comedy and he's coming across like a fucking fuck. You need to tell friend that he isn't in high school anymore and that he either needs to grow the hell up or start putting his emo shit in his LiveJournal rather than bothering you.
posted by Loto at 8:12 AM on December 9, 2009 [6 favorites]

Friend behaving inappropriately. Friend thinks you should be having sex with him even though you have made is clear that is not what you want. Friend displaying many red flags. Friend probably thinks of self as Nice Guy to whom sex is owed. Friend is incorrect. Friend who is passive-agressive and makes nasty comments on stranger/boyfriend's blog not much of a Friend, making quick turn into Creep territority. Tell Friend this behavior 100% not okay.
posted by Optimus Chyme at 8:12 AM on December 9, 2009 [15 favorites]

*much less chance of him
posted by ElmerFishpaw at 8:13 AM on December 9, 2009

Oh, God, I've been through this. But I was Friend. This is back when I was in high school, and I was a complete, insufferable asshole during this time period.

You can't get them to be friends. It's never going to happen. You spurned him, and so, in his mind, he's comparing everything that the Boyfriend does to something he'd do. Every time my best (female) friend would talk about something that her boyfriend did, I'd immediately follow it up with how "I'd never do that to you," or, "Man, he sounds like a dick." Mind you, the guy wasn't a knight in shining armor (or maybe he was, I can't honestly give you a clear judgment on that), but all I saw were the negatives, and how I could be the better boyfriend if only I convinced her to love me!

Yeah, it never happened.

You need to take a break from Friend. He needs some time to be pissed off, or go through whatever emotions he needs to. I had to see this every day (because of high school), and it about killed me. You have the option of distance. Let him know that you don't appreciate the comments, and that his behavior hasn't been acceptable for someone that you consider a friend. Don't try to get them to be buddies - it isn't going to happen.

If you're lucky, Friend will find a girl and this will blow over. If not, then it may take a while for emotions to level out.

Sorry this had to happen, but having been on the other side of this, I know what what I needed (not what I wanted) was some distance and some time to deal with my own emotions. If he refuses to disengage, even if you attempt to, force it. He needs to be an adult.
posted by SNWidget at 8:14 AM on December 9, 2009 [3 favorites]

Most friends know better than to do this, even when the significant other is really a lemon. Tell him he needs to be supportive for a while even if he feels differently, because it's affecting your friendship.
posted by xammerboy at 8:16 AM on December 9, 2009

I once told a dear friend that I didn't want to ruin our friendship when he professed his feelings.
His response: "I do! I've been waiting to ruin this friendship forever! Can't we just go ahead and ruin it already?"
Funny, but telling.

It wasn't ever really a purely platonic friendship, because one side is/was unrequited affection. Even though he says he is okay with just being your friend, and maybe he wants to be, he isn't, pure and simple. You won't be able to be super close friends, the kind who hang out alone and talk for hours and are always together, because it will be charged with sexual tension. (I'm starting to think this is almost always true - thank you, Billy Crystal and Meg Ryan.) Unfortunately, it's not a silly reason to stop being friends. In fact, it's a pretty common one and one you have to respect, especially because right now he's not acting like a friend. He's acting like a jealous jerkface.

Once you've made clear the boundaries of your friendship (like, um, no trash-talking the current bf), you will have to wait until he is ready to be your close friend again, if ever.
It can happen - the guy from my story and I have somehow managed to stay friends. But it took a long long time, a lot of hurt feelings, and we're definitely not as close as we were before. YMMV.
posted by bookgirl18 at 8:19 AM on December 9, 2009

Does this remind you of anyone?

Anyway, stop talking to your friend for a while until he gets over it. It has nothing to do with your boyfriend and everything to do with the fact that your boyfriend isn't him.

If you dump your BF and date another guy, he'll act the same way.

Alternatively, whenever he does complain about your B.F you can start up with "No..." and just start talking about how great he is, how passionate and how great in bed your boyfriend is, how into him you are, etc. That will really be painful and might get him to stop cutting him down.

But sadly he's jealous and he's just going to hold your friendship hostage until you relent.
posted by delmoi at 8:22 AM on December 9, 2009 [6 favorites]

If any of my friends did things like this, they would no longer be my friends.
posted by M.C. Lo-Carb! at 8:22 AM on December 9, 2009 [3 favorites]

I dumped a boyfriend because of just such a scenario. A friend of my BF hated me, trash-talked me at every opportunity. BF sided with friend. Yeah, that didn't end well.

In essence, your friend is telling you that he doesn't respect your decisions, that he knows what's good for you better than you do. Frankly, I wouldn't be OK with that - I can make my own mind up, thanks.
posted by LN at 8:25 AM on December 9, 2009

You can't fix this for Friend, because you didn't break it for Friend. Friend is choosing his behavior and will only change his behavior if and when he chooses to.
All you can do is define (for yourself) clear boundaries whose breach you will not accept, make those boundaries clear to Friend, and keep true your decision. No more negotiation over his behavior - when he crosses a boundary, break off the conversation, and if it continues despite that, break off the friendship. This person is not treating you as a friend, and whether he once was one or not, you don't need to accept this behavior from anyone. It's not an easy choice to make; you still want the friendship you used to have, but he's changed that and it's different now.
I'm sorry you're going through this; losing a friend is hard. I hope he'll get the message and you'll get your friend back sometime.
posted by TruncatedTiller at 8:26 AM on December 9, 2009 [1 favorite]

He is probably going to cast himself as the victim when you call him out or cut him off - he'll interpret it as your choosing the boyfriend over him, instead of a consequence of his inappropriate behavior.

In which case you should spell out very clearly that you are not and will never be interested in him romantically, and if he is not comfortable with that, or if his friendship is contingent upon your perceived availability, then the friendship is not going to work.
posted by Metroid Baby at 8:28 AM on December 9, 2009 [1 favorite]

Essentially the problem is your friend's feelings and unfortunately you can't do anything about that. The best you can do is decide how you want to handle it, because he has made it clear that his way of dealing with his feelings is to tear down your BF and make you feel guilty.

I would say that you always end up apologizing when you try to explain your problem to your Friend, is a red flag. He is trying to make you feel like crap and that is not very friendly.

I would dump the friend or at least tell him to back off until his feelings subside. Understand that you might lose this friend, but that might not be so bad if he keeps doing this to you.
posted by poyorick at 8:29 AM on December 9, 2009 [2 favorites]

Yeah, you know, out-loud passive aggression towards important people in your life? Not a good quality in a friend regardless of whether or not you'd fuck them.

Dude needs to grow up, and he's not going to do that while he still thinks he has a shot with you. He's going to think he has a shot with you as long as you keep hanging out with him and apologizing to him. So stop apologizing and tell him you can't stand the way he treats the people in your life, you don't like how he acts towards you, and you can't be friends any more.

Then stick to it, and go enjoy your actual productive friendships and relationships with people who are respectful towards the other folks in your life.
posted by fairytale of los angeles at 8:30 AM on December 9, 2009

Friend has left nasty comments on Boyfriend's blog.

And that's where it got creepy.

This relationship with your friend, one way or another, now or later, is not going anywhere good.

Now would probably be a good time to start that drifting apart.

Also, I'm sorry I can't think of a gentler way to say this, but you're deluding yourself if you think they can be friends in this circumstance. That doesn't really happen. Your friend liked you, you rejected him, now your with someone else. None of this is mitigated in the least by anything they have in common.
posted by A Terrible Llama at 8:41 AM on December 9, 2009

What you need to do:

Send Friend a link to this discussion thread.

He'll work it out, and you can be friends again. Or he'll have a hissy fit, and you shut the door as you would on someone else's child in a tantrum. Either way, the situation is resolved.
posted by lapsangsouchong at 8:42 AM on December 9, 2009

I would question whether this guy was ever really your friend. Your relationship has been a friendship on your end, but he has always had the motive of trying to date you and now that you are not doing what he has so carefully planned out/manipulated, he is using all the information he knows about you, everything that you trusted him with, against you?

I know it hurts to know, but while you might have been his friend, this guy has always had his best interest in mind first.
posted by spec80 at 8:43 AM on December 9, 2009

You said:

This seems like a silly reason to stop being friends.

And if the problem was that your boyfriend doesn't like your new boyfriend than it might be. But that's not your problem.

You aren't having a trouble with your friend because of your boyfriend. You're having trouble with your friend because he's not your boyfriend. This all goes back to your rejection of him. You having a boyfriend crystallized that rejection.

No matter what your past history with your friend is -- I don't care if he pulled you from a burning building and gave you his kidney -- treating you and your boyfriend this way is not acceptable. It'd be bad if he was an acquaintance; from a friend, it's unacceptable.

Tell him to suck it up and stop it or he's going to lose your presence in his life. Then it's his call.

P.S. My advice would be different if you and your friend had been nebulous or unclear regarding the status of your relationship prior to your new boyfriend. I'd be cutting him some more slack. But he told you what he was interested in and you told him you weren't into him that way. By treating you this way now that you have a boyfriend shows he didn't accept your answer and respect your friendship enough, and though he may have issues with it, since you have made your level of feeling for him abundantly clear, it is up to him to deal with it.
posted by MCMikeNamara at 8:45 AM on December 9, 2009

Friend is not being much a friend.
posted by DeltaForce at 8:48 AM on December 9, 2009

Friend is not necessarily a real friend to you as Friend is acting more like a guy who wants to date you, rather than as a real friend. Stop talking to Friend for a while, tell Boyfriend that Friend is acting insane. Maybe Friend will snap out of it one he gets a girlfriend and come back and apologize to you. But, right now, Friend is being sort of emotionally abusive toward you (seriously, you apologizing in every conversation?) and you need to remove yourself from that situation.
posted by mustcatchmooseandsquirrel at 8:48 AM on December 9, 2009

Though context makes it obvious, my comment was supposed to begin

"And if the problem was that your friend doesn't like your new boyfriend than it might be. But that's not your problem. "

Though that Freudian slip may just show what it seems like your friend has in mind.

I also wanted to say, though it may seems like we're all piling on your friend -- who is obviously someone you care about, otherwise you wouldn't put him with his crap -- please don't ignore this "tough love" advice. We can't really know his motivations better than you -- and though he may have wanted to date you this entire time, that doesn't mean he also doesn't want to be your friend. Just let him know that now is his time to prove that to you by adjusting his behavior to how a friend should behave.

Good luck.
posted by MCMikeNamara at 8:54 AM on December 9, 2009

Initiate Thumper's Mother's Rule to Friend. Tell him If you can't say something nice, don't say anything at all. And back it up. Refuse to listen to him spew about Boyfriend. Express displeasure at the rude and immature comments on Boyfriend's blog. Create distance between you and Friend, and tell him why--"I don't like how you're acting about Boyfriend, and it's got to stop. If you can't stop, then I won't spend time with you or talk to you as much. Your call."

Friend then has two options: drop you entirely or get over himself. There are a lot of posts here that could have been written by Friend, and the advice to him would be to take the space and stay away from you until his feelings have passed. It's really hard to get over someone when you really like them and they like someone else, and you're spending all your time and energy focused on their relationship. But it can be done.

I was you about ten years ago. I told Friend everything I said above, and we didn't speak for about a year. He got over himself, and I'm now celebrating his impending fatherhood. I'm friends with his wife, and everything's fine. But we needed that space and time away from our friendship.
posted by peanut_mcgillicuty at 8:55 AM on December 9, 2009

I want to say that the friend is just jealous and wrong, but the last couple times I remember being accused of being "that friend" myself, the perfect boyfriend before long was revealed to be exactly what I said he was. It's not always that simple, and in fact crappy guys commonly use the "they're just jealous" comment as a way to dismiss any unflattering opinions about themselves held by "friends" -- which works disturbingly well.

But even if your friend may have a legitimate concern about the boyfriend that you haven't recognized yet, there's still a right and wrong way to handle things. A friend who is truly looking out for you will share their concerns with you about the person once or twice, but not keep harping on the issue once you've made your decision; a friend just doing it out of jealousy will make a sustained and consistent effort to rail endlessly on the topic, because they are trying to tear the relationship down.

It sure sounds like the latter, here.
posted by Pufferish at 8:56 AM on December 9, 2009 [2 favorites]

I want to say that the friend is just jealous and wrong, but the last couple times I remember being accused of being "that friend" myself, the perfect boyfriend before long was revealed to be exactly what I said he was. It's not always that simple, and in fact crappy guys commonly use the "they're just jealous" comment as a way to dismiss any unflattering opinions about themselves held by "friends" -- which works disturbingly well.

but that's for the poster to figure out. The "friend" has a conflict of interest that puts him out of the place where he can be expected to provide neutral advice. Dude has to stop the hating, no matter what.
posted by Ironmouth at 9:07 AM on December 9, 2009

Pufferish makes a good point that there is a non-zero chance that Friend is right about this, and that's something to be considered, but I'll nth everyone else's words that he's just being a dick overall about everything.

I'm not with the group that thinks you should do this in a subtle way at all, trying to send hints that this is unacceptable. I think you've already attempted to curb this behaviour in a roundabout manner, and ended up apologizing (?!) through some kind of jedi mind tricks he plays in arguments. I think you need to say something like what restless_nomad suggests. Simply offer an ultimatum, this behaviour is unacceptable, and if it doesn't stop, immediately, like, right after you finish typing this sentence, then you'll have no choice but to begin to pull back from this friendship. Friend's words make you sad, uncomfortable, and somewhat angry. That's not how you want to feel when you interact with Friend, so tell him, clearly. If he continues to behave this way, he's not really a Friend, and you need to pull back, while telling him specifically that this is all his doing, and now he's lost you forever.
posted by dnesan at 9:12 AM on December 9, 2009 [1 favorite]

Yeah, jealous. I know two dudes that should be the best of friends, but they're both into the same girl (who has a boyfriend) so they fucking haaaaate each other.

Now that's a movie. Don't know if it's a comedy or a psycho-thriller. Probably both.

If any of my friends did things like this, they would no longer be my friends.

Because, if the word "friend" has any meaning beyond familiarity toward someone you're not sexually involved with, it's that when push comes to shove, they're on your side. This guy is not on your side. He's playing transparently Machiavellian games in hopes to claim the prize that is "You". Creepy and immature.

I have a long-standing friend who went through something like this (he was the "friend"). Call him Pete. Pete wanted his best friends girl. She just wanted to be friends. Best friend and girl eventually parted ways. But she still just wanted to be just friends with Pete. She worked through various other relationships with other men. Pete never gave up "trying", even had a few trysts with her eventually, but then she finally moved to a different continent and asked him NOT to follow.

This took almost twenty years.

Even now, another ten years later, I doubt he's over her. Still a bachelor and all. But at least I no longer have to listen to his deadly boring stories of desire and imagined conquest.
posted by philip-random at 9:16 AM on December 9, 2009 [1 favorite]

I've been in your shoes, pretty much exactly in your shoes, to the point where BF and I joked about F pissing in the corners of my apartment to mark turf. You really need to tell F to back the hell off. It's probably going to ruin the friendship, but as others have said, the problem here is that you're not dating F, and that's not your problem. It's F's problem and he's dumping it on you. Good luck dealing with him.
posted by immlass at 9:21 AM on December 9, 2009

I'm really sorry, but this friendship has been over for a long time. This fella should have moved on when he was spurned, but instead decided to try and make the almost-always-disastrous Escape From the Friendzone. What was a "That Was That" for you was probably a long, slow slide into frustration, obsession and routine, self-inflicted disappointment for him. He likely fancies it "romantic" that he's willing to be "there for you" at all times and I'm almost certain he's telling himself stories about his own gallantry in suffering through a connection with you that is so unsatisfying for him. Which, of course, only tightens the grip that the Nice Guy Fallacy has on him right now.

He's probably not a bad person, but his interactions with you are not at all genuine right now. He's too overwrought and wound up - he'd be pulling this same shit no matter who you were dating. If this friendship has any chance of being salvaged - indeed, if it has any chance of being an actual friendship again - it first needs to be put in cold storage for a long time. You guys need a lottabuncha space for a damn long time - like, a season or two, minimum. Long enough for this guy to make his own moves, abandon the you-related hopes which are only hurting him right now and find love with someone who can love him back.

This is High School stuff. This is his chance to be rid of this behavior. He won't see it this way at first, but you pulling back from your relationship with him is the only way you can care for him right now.
posted by EatTheWeak at 9:29 AM on December 9, 2009 [3 favorites]

What EatTheWeak said. There are a million AskMeFi questions from people who are the Friend, and the answer has never been (to my knowledge) "quit the crap and just be friends with the lady/dude." Confrontation will likely be pointless, and you two can't be friends because he pines for you. Maybe not "End of Story," but probably.
posted by rhizome at 9:40 AM on December 9, 2009

Well, I agree that Friend needs to get himself under control -- the nasty comments on Boyfriend's blog are not cool -- but with all due respect to the OP, we are seeing this drama from only one point of view. Friend almost certainly has a very different view of his role in the situation. In particular, there is nothing in the post about how Friend has formed this opinion of Boyfriend. Have they ever met? Is Friend forming his opinion based on what OP tells Friend? And for that matter, what is Boyfriend's opinion of Friend? We get a single acorn of statement ("Friend has decided that he hates everything about Boyfriend") and I see huge forests of speculation growing from this.

I have been both Friend and Boyfriend in my life (as well as being in the position of the OP at another point) -- in fact, if I were reading this in about 1993, I could be wondering if this had actually been written by a woman I knew then with me cast in the role of Friend.

When I was Friend, my closest friend (in the same role as the OP here) was going out with Boyfriend. He treated her incredibly badly in my view, but as she said at the time, she had no need to tell me about the happy times they had together. I was her outlet for all her frustrations. She only ever told me about when he insulted her and mistreated her and how Boyfriend's mother compared her unfavourably to Boyfriend's previous squeeze, who could do no wrong. I am sure she and Boyfriend had fine times together -- they were together for four years -- but from what I as Friend heard about it then, it was misery. On top of that, although Boyfriend had never met me, he was insanely jealous of me because his girlfriend and I had a long-standing friendship and connection that he never managed to have with her. And he could not understand that I might like her without wanting to sleep with her; I had had a crush on her years before, but it was long gone by then. In my position as Friend, I parsed this as him being unable to think his girlfriend could possibly be of any interest to anyone except as a receptacle. So of course I thought he was a twit. Boyfriend gave her an ultimatum or two about spending time with me, but thankfully she was strong enough to tell him to grow up.

And as an aside, the Gordian Knot DTMFA approach I see so frequently in Relationshipfilter questions makes me tired in my soul. The OP is pretty upfront about Friend's importance: "Friend has been there for me, we've been there for each other, through some extremely difficult times and some of my happiest memories have been with him." Where I come from, someone like that is not to be lightly tossed aside.

So: Friend needs a good talking-to about his conduct and an honest discussion with the OP over whether or not he still has feelings for her (I am going with the assumption that this the OP is female). OP needs to make her displeasure clear and the fact that Friend's remarks are hurtful even clearer. OP should ask Friend why he feels this way about Boyfriend. If I were Friend, the best thing I could hear would be: "Look, you and he are both very important to me and I don't want to lose either of you. I wouldn't be with him if he were insulting you all the time and it makes me very uncomfortable when you insult him. This is a side of you I really don't like seeing, and it's making me think less of you. If you cannot get past your problems with Boyfriend, you and I have to take a break for a while."
posted by ricochet biscuit at 9:41 AM on December 9, 2009 [1 favorite]

You might mention how exciting it is when Boyfriend runs his hand down your side, and how you sometimes moan softly as his hand slides down your thigh, and as you turn into him for the warm, soft kiss you've come to long so deeply ...

Hmm, okay, maybe not. But it'd be fun.

Friend is being Jerk. Might in fact be Jerk. Tell Jerk this jive stops or else. No more apologizing. None. Nada. Zip.

I think Friend is Goner, frankly; anyone who acts like Jerk as consistently as he has probably is Jerk, or Mope at the very least, and in either case you don't want this person in your life, whether this thing with Boyfriend stands the test of time or not.

Wave him goodbye, then turn into that kiss......
posted by dancestoblue at 10:49 AM on December 9, 2009

I would outright tell the friend that every time he makes a shitty comment about your boyfriend and otherwise acts psycho, it makes you really grateful you didn't date him. Harsh, yes, but it doesn't sound like he understands anything nicer.
posted by Nattie at 11:32 AM on December 9, 2009

So I dated this girl once, in high school. It was, at first, a good relationship, but eventually it became bad and finally it ended.

When I told another friend of mine this, and he said "well, come on out tonight; a bunch of us are going to a movie, and you could use some friendly people to hang out with." I went, and just about everyone I knew in school was there, and I suddenly realized that I hadn't seen many of these friends in quite a while -- in fact, since I started dating the girl.

I mentioned this to the friend who'd invited me out, and he said, "well, yeah, none of us could stand her, but you were happy, so nobody wanted to say anything. But now I can tell you [really rude but funny thing about his opinion of her that, if I shared it, would become a huge thread derail.]"

That is what friends do; they trust you to do what's best for you, whether they like it or not, so long as it isn't hurting you -- and if/when it does hurt you, they welcome you back with open arms and support you.

YOUR friend? Not a friend, just someone with unrequited love who can't move on with his life. He needs to go.
posted by davejay at 11:39 AM on December 9, 2009 [2 favorites]

I disagree wholeheartedly with Ricochet Biscuit, insofar as I can glean from your post. It may be the case that this friend has been there for you, but since he professed his attraction to you, that friendship has always been conditional on you not being with someone else/paying him as much attention as he needs.

The way he is treating you is totally self-serving and inappropriate. While I don't believe that you need to DMTFA permanently, you need to give this guy a break. Giving him a break will be very telling as far as your friendship is concerned, because it will shake out in three ways:

1.) He takes the time and comes back and apologizes for his behavior, and acts right from there on out. Great, you can be friends again.

2.) He takes the time and never returns. Sad, but if you make let him know the door is always open for him to return if he can straighten up, it's his decision.

3.) You ask for the time apart and he chooses not to honor it. This, unfortunately, is what I see as being most likely. cutting him off is probably going to ramp up this behavior for a little but. But it will calm down. This, however, send a clear message: your friendship is done.

He needs to know that this behavior will not be tolerated. To remain his pal is to continue to tolerate it. Let him go for a while. If he's half the friend you seem to think he is, he'll come back with his head screwed on straight and apologize for his asinine behavior. Otherwise, he wasn't the friend you thought he was in the first place.
posted by orville sash at 11:42 AM on December 9, 2009

Wait, what? I'm surprised you're still friends with this person after they left nasty messages on your boyfriend's blog. That's beyond just finding someone distasteful and borderling psycho to be quite honest. Even taking out the fact that he has had (and obviously still has) feelings for you, any friend of any sex taking the dislike to that level is very disrespectful. I don't care how much of a close friend he's been before, through thick and thing, this level of disrespect should be a clear red flag. He's not only showing a clear lack of respect of your feelings, but he's also showing a clear lack of respect for you as a person and the choices you make and also disrespecting your relationship.

AND, I'm going to add you're not really showing your boyfriend much respect here either. If you're not ready to cut things off with this friend for his unacceptable behavior, are you ready to end things with your boyfriend? Because boyfriend might be endlessly patient now, but if you're going to let this sort of thing continue without any real consequences besides a verbal smack on the nose with a rolled up newspaper, then don't be surprised if he gets fed up with this shit. The issue here isn't just your patience running out, but also your boyfriend's. This friend is not just dissing your boyfriend, he's also dissing you and I doubt it's specifically this boyfriend that's causing his behavior unless there's something unsavory about the boyfriend that we don't know here, and even then there are plenty of ways to handle the situation in a much more mature way. Are you willing to continue to be friends with a person who acts this way? What happens if (IF, not saying will, for all I know you and the boyfriend could live happily ever after, but hypothetically) you find yourself not in this relationship anymore and in another one? Why put up with this type of underminer who's just trying to sabotage your relationship? And trust me, I've been in a similar position and the spurned party did go from just expressing dislike to doing little things that sabotaged a relationship that I didn't even realize until the relationship ended (the bf told me things that this person had told them about "what happened between us" that wasn't true at all, but I had no idea this person had said such things, though the fact that the bf believed this person over me was more of the bigger issue, but that's neither here nor there, the point is it obviously didn't help), and this was looong AFTER I'd stopped talking to the person because their whining about me not liking them back and liking someone else got annoying as hell and a little creepy.

Look, I'm not saying don't talk to this friend ever again, but I honestly would say, "Dude, you need to fucking drop it and get over yourself and the next time I hear you say something or even roll your eyes about him, that's the end of the conversation. If I ever see another mean comment on my boyfriend's blog" and SERIOUSLY back it up and put some space between you two so he has a chance to get over it because he apparently is not over it. I know you consider him a close best friend, but sometimes clinging to that is just as damaging if not more than if you'd just cut him off and let him go figure some shit out and maybe sometime in a future there's a chance this friendship can be salvaged, and even if you guys don't reconcile, sometimes a chapter just needs to close on a friendship for either parties to grow. Unless you're reveling in the drama, it's a little selfish to refuse to read the last page in that chapter so you don't have to close it. You can't make everyone happy all the time and sometimes that even means making someone unhappy for a short time.
posted by kkokkodalk at 11:50 AM on December 9, 2009

I disagree wholeheartedly with Ricochet Biscuit

... which is weird, because you go on to more or less paraphrase my advice. Yes, Friend needs to grow up or OP and Friend need to take an indefinite break. I said exactly this much, twice, in my answer. Where I differ with the prevailing opinion is that the OP needs to talk to Friend first and say, "Look, this isn't working. You may think you are saving me from making a mistake or something, but I know Boyfriend and you do not. Either you get over this and grow up, or we go our separate ways. What's it going to be?" I'm saying if Friend is shown the door, he deserves to know why.

This strikes me as roughly similar to a recent askme thread, which essentially dealt with a situation where the OP had complained that someone whom she did not want to hear from was harassing her because he had called three times in a year. The kicker was that it seemed the OP there had had never actually asked him not to call her. Unless Friend gets the talk, that is Friend in a year (or less -- if I thought someone I knew was in a bad relationship and she was suddenly cut off from me, I might try harder to get in touch).

Look, as I said, fifteen years ago I was in a place not unlike Friend. I was not posting insults about Boyfriend publicly or anything, but my closest friend was dating a guy who made her miserable every time I talked to her. Of COURSE I was critical of him to her. After a couple of years, she got out of what she now describes as a physically and emotionally abusive relationship. (Not that what the OP here is in is that, but we are talking about Friend's perceptions of the situation.) I am very glad that my friend fifteen years ago did not have the counsel of a bunch of anonymous internet yahoos telling her to cut me loose "because [I] clearly can't let go".

Friend is not here to offer his view of the situation. I think Friend is being childish and may still very well be suffering from an unrequited hopeless crush, but I allow that he thinks he has valid concerns and might just be looking out, however misguidedly, for someone he cares about.
posted by ricochet biscuit at 1:44 PM on December 9, 2009

Friend is not a friend. Friend is abusively violating common rules of decency. This has little-to-nothing to do with you, nor your boyfriend, except that you two are players in Friend's little childish drama.

DTMFA - referring to Friend, of course.
posted by IAmBroom at 2:24 PM on December 9, 2009

So assuming that you don't want to dump your friend completely (although the blog thing is quite egregious)...

Every time he does something wrong and you apologize, you're not telling him "I'm sorry", you're telling him "I care more about your feelings than I care about my boundaries, so if you get angry or upset, I will let you violate my boundaries."

Email friend: "We will no longer be talking about boyfriend. Don't bring him up again."

No matter how he responds, don't apologize. Don't answer his calls or read his emails/IMs for a few days so he knows you're serious and so you don't backpeddle. If you mainly apologize on the phone/on IM, try to avoid talking to him in real-time and keep it in email, where you can think about your response.

The next time you talk on the phone/IM, if he asks about boyfriend, say "I don't want to talk about it." If he keeps talking about boyfriend, hang up or sign out. Don't answer his calls/IMs/texts or read his emails for a few days so you don't backpedal out of guilt.

If he emails with comments about boyfriend, respond with one line, pre-written, and the same exact line every time he does it:

"I didn't read this email because you mentioned boyfriend."

Good luck.

On a general note, if you only say "I'm sorry" when absolutely necessary, people will respect you more. They will also like you more, because people like people who like themselves. This is especially true when you're dealing with men, because they don't apologize as much as women, so they tend to react to it as though it reflects a lack of competence, confidence and/or self-esteem.

If you don't want to argue and you want to avoid apologizing, how do you deal with arguments? Active listening ("I can tell that you're upset"), and if it gets to be too much, leave the situation. There is nothing to be gained by letting people bully you into getting their way.
posted by kathrineg at 2:47 PM on December 9, 2009 [1 favorite]

Boyfriends-in-waiting are not your friends. This guy is not your friend. All the good things he ever did for you were just trying to get into your pants. If he was actually platonic about you and your actual friend, he wouldn't be acting like this. Now you're not letting him fuck you, but you're letting someone else, and he is pissed off.

Not your friend. DTMFF.
posted by jenfullmoon at 3:14 PM on December 9, 2009

On a general note, if you only say "I'm sorry" when absolutely necessary, people will respect you more. They will also like you more, because people like people who like themselves. This is especially true when you're dealing with men, because they don't apologize as much as women, so they tend to react to it as though it reflects a lack of competence, confidence and/or self-esteem.

I don't really think that's the case. I mean, most people don't run around trying to calculate how much self esteem others have.
posted by delmoi at 5:52 PM on December 9, 2009

People notice if other people seem confident. We are a social species. Conscious "calculation" --some of us. Unconscious judgments--the vast majority of us. Consider a previous AskMe where a man asked for role models of strong masculinity. The people in his workplace perceived him as weak and took advantage of him because of it. They borrowed money from him and didn't bother to pay him back. Did they have a checklist on the office refrigerator? No. They based their opinion on their social interactions.

Some people say they're sorry too often. If a woman apologizes so much that she apologizes when someone wrongs her, as in the original question, she will benefit from consciously noticing and curbing that behavior. Complicating things, what women mean by "I'm sorry" is not necessarily an apology--but an apology is what men hear. I specifically mention men because men jockey for status in a specifically male way. Behaviors that might be neutral or positive in a female space (apologizing easily) are not necessarily beneficial to a woman in a male space.

As necessary for this medium, my comment teems with generalities--for specifics, check out the works of linguist Deborah Tannen (and her various collaborators).
posted by kathrineg at 11:06 AM on December 10, 2009

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