I should feel bad, but I don't feel bad.

a reply to: NarcolepticBuddha

Call him out by name then, and try to talk - If he's in the state you are describing, try to talk to him just to see if he'll open up. You don't have to say how you know him (pass it off as another friend, relative, uncles's cousin's second wife's boyfriend).

He's not going to accept he needs help as is: Talking with him is one way to maybe convince him to get the help he needs. No-one says you need to invite him out with you for drinks; just ask him how he's doing. If you find that he seems more open to talking, try to casually work help into the conversation ("I'm not sure if you knew this, but there is a restaurant down the street that offers free meals to those in need on Sundays; have you been there before?").

Giving advice and tips like that is on you - it's up to him though what he does with them. He might listen, he might not. But there's only so much that you can do, and you need to take care that this doesn't drag you down with him if anything fails.