That's a better direction to take this thread and I find it admirable that you are trying this hard to help the guy. I'd be careful about doing this solo. He's just going to take it as an assault on his identity and he might take to blaming you for his problems. You might want to take more of an intervention approach with a couple of your friends. Start with stuff within your own personal experiences as opposed to things that were said by people not present (such as girls). Creepy, inappropriate jokes might be one. I think this thread now deserves the attention of @cooks1 who is totally awesome at figuring stuff like this out.