One of my best friends asked me to be his best man a little over four years ago - every time I tried to prod him into action over the wedding various excuses were always forthcoming. Now it’s clear his relationship is a staid, horrible place to be - I confronted him and told him to get the hell outta there. Knowing he wouldn’t be able to fob me off, he just came back with straightforward honesty: “I hate it. But I’m not going to change it - I can live with this shit for the rest of my life if I have to…”

The problem? I loathe her boyfriend and she knows it. Her and I stopped talking for a while because he was such a prick to me. We were never fighting but we stopped hanging out at all. Now all of a sudden she comes to me with this?! Ya, I’m not sure what to do either.

A particular situation comes to mind for me. I had a friend who engaged in risky behavior (not sexual). It was awful to watch this person sort of wither away. They were always angry, sad, and hateful. They seemed - to me - to be spinning out of control. I was going through my own crap at the time (tumultous break up which was very on again/off again, new job, new town, feeling lonely, etc.) so I didn’t handle this with the grace and dignity that I wish I had now that I look back, but I know that my heart was in the right place. Eventually we had a blow up and stopped speaking. I later apologized for my mistakes but this friend did not. I feel helpless for them because I imagine their problems were not exactly situational like mine, that it will stick with them for the rest of their life. I also feel sad because I can’t be there for that person and when I had the opportunity, my own crap got in the way (not to mention how frustrated I was with them). But mostly I’m sad that I couldn’t stand by this person. It eventually became too sad to watch this person self-destruct and, honestly, we are both probably better for the lines of communication being broken.

I think you know your situation best so only you can handle it in a way that would honor your friendship and personal style. Sometimes it helps to stick around and support the person, but there are times where you, as a friend, need to put your foot down and say “ENOUGH!” I think it’s always a good idea to step back and examine the situation. In my profession, I find that when I’m becoming more worried/upset/frightened than my clients about their situation, it is probably a good time to re-evaluate my role as a professional (or, in your case, as a friend) and their role as the client with the problem. There is something inherently wrong with the notion that I am more worried about their problems than they are! People have to be ready to put their emotional and physical needs on the line before they can truly move on and/or reach out for help.

I’m haivng a similar thing now with another friend, the guys finally gone but now we’re trying to convince her not to seek revenge on every guy who she meets, even if they do nothing to warrant her being mean to them. Sigh.

One can only hope your friend comes to her senses before she gets in any deeper.

However, as friends, the best we can sometimes do is be there for them, unconditionally, until they are ready to make the leap on their own to move on. It’s a long har arduous process and sometimes we can’t be strong enough, but it’s the best we can do.

In the end, I came to my senses, and they were still there for me, because I was a hot mess after that relationship (as abusive as it was). It’s frustrating, but it’s one thing I know, is that once your friend realizes, and finally has the strength to leave him, she’ll need all the love she can get. You’re already a great friend for caring.