Okay some background first I suppose.
My friend, let's call him Jake, and I have been friends since after High School and all through College. We've known each other for more than 10 years now. We use to be roommates and we had a great friendship. We eventually moved away from each other, him to FL and myself to NYC. During that move we lost contact with each other for a couple of years.
Well we reconnected when I found him on Facebook, and we are getting our friendship back on track for the last year or so. However, since we reconnected I found that I'm serving more as the sounding board to his endless complaining. About losing his last job due to some error, his inability to get a new job in his financial field because of some problem with a U5 form (whatever that is), hating his new job, about his family not helping him, about not being able to do whatever coursework he has for his masters, about his latest speeding ticket, about him gaining weight, about his girlfriend gaining weight, about whatever shit his boss is giving him... The list goes on and on and on.
The last time we talked about anything and I mean anything not related to what his current problem is was probably before we lost contact about whatever various Geeky things were currently out.
I've tried steering the conversation to geeky things, even geeky things he likes that I'm ambivalent towards (He loves True Blood and I can take it or leave it) in attempts to steer the conversation to anything else. And it works for all of 5 mins before he goes back to complaining about something else (big or small) and it just drags me down. I've tried giving some advice or another perspective on things thinking that is what he wants, but he promptly ignores it and restates the problem as though I somehow missed it or failed to understand it
Now I understand that as a friend I should be supportive friend guy and I was in the past and try to be now, but the whining is so endlessly relentless that I'm beginning to dread speakng with him because I'm going to spend the next several hours talking him off whatever ledge he is currently on.
I've tried telling him maybe a therapist/psychologist would be helpful for him, since he seems to have some deep issues concerning several things, he has severe sexual hangups. And he kind of just scoffs it off with something about being last time he went to one which was during high school, he was given some kind of medication which made him feel high all the time.
So anyone have any idea what I should do here? I mean he was my best friend and I love the guy to death, and I'm just at my wits end here.
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I mean, don't be an asshole about it; just sit him down at some point and say "dude, you know I love you, but lately, you have been such a downer. You're always complaining about something. And I don't mind if you do it sometimes, or even a lot, but it's a bit much for it to be all the time."
If hes in a tough spot and determined to whine, You aren't being a bad person if you want to step down from the honorable position as his free and unappreciated therapist. The fee for that, if nothing else, is at least personal interest in your happiness and well being in return, and he doesn't seem to want to extend that to you.
If you think hes in a super tough spot and this it temporary, I would still push him to talk about other things and gently remind him that you aren't the deposit box for all his bitching, and see if the relationship holds up.
Thanatos is dead on with this, it's not going to change unless you meet it straight on. I am really glad that none of my close friends are like this, but then, they all know that they would just be ridiculed for having sand in their lady parts.
You have to just flat-out tell him. Be nice about it and all, but don't dance around. It's ultimately kinder to give him a real chance to fix it than it is to be passive till you blow up at the guy or cut him off, when he won't understand why. Chances are really good that he doesn't realize how much he complains.
It doesn't mean he can't come to you with problems and you should tell him that. "Coming to you with a problem" isn't really the same as "constant crushing negativity", though.
And to that end, helping him to realize this is a manner of being a good friend.
I had a former friend who did this constantly, and would never listen to advice. After about eight years of putting up with that (and him consistently doing things to put him in a spot where he could complain), I stopped. I determined that he was only happy when he was bummed out because it made those around him sympathize for him and he got something from that.
Your best bet is to talk to him as others have advised. However, if you do talk to him and you meet the same outcome I did (which is that he kept complaining and did nothing to help himself and refused help), you might have to re-evaluate how much you want to be friends with this guy. It's not wrong for you to put your needs first. Its definitely not wrong to take a step back from your friend if you've tried to help him loads of times and he refuses to do anything for himself.
take it from there