*Gives a point to PocoDiablo*
I have someone very similar to this guy on my MSN list. It seems like he likes to throw loud, frequent pity parties. Personally, I have no patience for that kind of crap. If you're willing to extend your hand toward him while he just looks at it and sinks deeper, feel free... But if it were up to me, I'd just walk away.
Besides, what happens if you do get closer to him to try to help but end up getting fed up in the end? The closer you get to him, the more it will hurt him in the end.