Those situations where it sucks to be someone's friend, you know what I'm talkin about...

What is the most precarious situation you've been in as a friend? Family works too...
Did it work out for you in the end?

I was in the awful situation of being friends with both parties in a couple. She cheated on him twice and I had no clue how to tell him, but she certainly wasn't planning on telling him. I decided on just telling him she cheated and not paining him with any details. Big mistake. He ended up getting fed a bunch of crap by his girlfriend and still doesn't know how evil she is. FAIL.