I like Bill's post too. I would say though, I think its okay to give an opinion or advice if its requested by your friend. I think its also best to ask him if he wants your opinion / advice first, before giving it. And if it does upset him, consider not doing it in the future. I like etcetera's post too. You are not responsible to fix this, and can't. I think just being a caring friend and listening works too. But if you are sick of listening, know its not your job to listen, and you can find a way to tell him its upsetting / draining and you don't think you can listen as much. Though it doesn't sound like this is the issue. If you've already said something and worry it was harmful or just not the right thing, check in with him / apologize, etc. But we are all human. We don't come with a communication book in hand - so don't beat yourself up.