How to stop being friends with someone...

I've had a long (and I mean LONG - going back 30 years long) history of befriending people that really need friends. Kind of like a Don Quixote thing. I also went through a really crazy college period, rife with deep depression and dark thoughts. In hindsight, I may have been going through alternating mania and depression. I befriended this guy in college. He is one of those guys who is his own worst enemy. He is a true pessimist, and has a victim complex. He never seems to be able to take responsibility for his own predicaments.

Well, of course this was exactly the kind of person I was drawn to - I could help him! It didn't work out so well, and during some (what I think were) manic moments, I got romantically involved with him, and that REALLY complicated things. I became part of his problem - I was truly awful in during my early 20s. Some of it may be related to bipolar issues, but in general I was not a good person. Things split off and I moved to a different town and he moved to a different town and you'd think I would never see him again.

Flash forward 4 years. I'm in a steady relationship and engaged to be married to a great guy. I have a decent job, but I'm looking for something more, when this guy kind of pops back into my life. We'd kept in slight contact over the years via email and icq, and he had moved back to my home town. The company he was at was hiring! It sounded like a great company, and so while I was home visiting family I interviewed and was hired. My finance moved back to my home town with me. Shortly after I hired on, my friend quit to go off with 2 of the partners who split off to form a different company. We stayed in close contact this time, socializing quite a bit. He got married, and then divorced less than a year later, and one of the reasons his ex-wife gave was me! Apparently she felt like she could never live up to what I was doing and who I was. Keep in mind I never even really felt like I had dated this guy - we were friends and I took advantage of his generosity to pay for things. So I was shocked, but I felt kind of responsible.

Mutual acquaintances are always asking me why I'm still friends with this guy. He complains all the time, he's usually very unpleasant, ALWAYS has to be right, gets violent with himself (punching walls), drinks too much, and apparently is still hung up on me. My instinctive response is that its my penance for being such a ***** to him in college. But that seems like a pretty weak reason to still be friends with someone from that long ago.

Well, now flash forward to current time. 2 years ago, I recommended that he come back to work for the same company. He was unhappy in his job (but he is ALWAYS unhappy...) and my company had a need for someone with his skills, so i thought it would be a win win. What a huge mistake!

He suffered under mismanagement for the first year, and then finally got a decent manager but was moved AGAIN 3 months later to a very junior manager and was put on really crappy projects. He's miserable, and his misery is dragging me down too. I just don't know that I can be friends with this guy anymore. I'm pretty sure he is going to be fired or laid off, and I don't have any desire to speak up for him At this point, it might be better for everyone if he went somewhere else! He is remarried, and his new wife is amazing. I really enjoy hanging out with her, and I don't have a ton of friends, so it would really suck to lose them, but on the other hand, I just don't know that I can do this anymore.

Should I try to protect myself by distancing from him or should I be a good friend and stay by and support him? UGH! I just feel like he is toxic, but that seems so selfish. Shouldn't I be trying to HELP him? But after almost 15 years, isn't that a sign that I really can't help him? I'm really torn up about this

Let his wife help him. I don't believe in cross gender friendships among married people, like you are describing. Find yourself some female friends. Nurture them. What happened with your sig. other? Are you two still together? If so, your guy can't be too thrilled with you having this male friend.

This friendshio hasn't been good for this guy. Now you're finding it's becoming a drag to you. It's gone on long enough, with nothing good coming out of it. Move on. Cut the strings.

I agree, it is a toxic relationship; despit the fact that you have benefited from the friendship in financial ways as well as emotionally, it is going to cause even more long term problems.
If you are still with your significant other and he doesn't express to you any feelings against the friendship than that is Because he is trying to be supportive- like at the cost of displacing his own feelings and internalizing his suffering-

Moreover, as you said that the friendship wasn't good for either of you. the fact that you can acknowledge your need for befriending those who are "in need of a friend" is great, this is a good step forward. Now you should share this with your partner, express that it is somethi g that you feel you need or that it is something that you feel is lacking.

It is always difficult to admit a flaw or to express our weaknesses, especially to those who we feel the most love for or in some instances to those who may be most hurt to hear it; however, knowing this will allow for your partner to best support you, it will create and strengthen the closeness between the two of you and will if nothing else build the trust between the two of you for your transparency. Remebdr that it will most likely be hurtful for ypur partner to hear and accept, but it will be so much less than the potentially dangerous results of what Continuing this type of behavior could lead to