Well, there's this guy I like, and we're really close friends. Problem is, he hates going outside. I guess that's pretty normal and all, and I can accept that, but generally if someone asks to hang out, you should agree, right? Especially if you get upset with yourself that you made that person mad. This happens to him more than once, and no matter what he still refuses to go anywhere.

I've tried coaxing him to going to places with me, but so far I've only had one success and that was only because I already rather depressed and started crying in front of him. Low blow, I know, but it wasn't really all on purpose. All other tries have been met with outright refusals and guilt trips to make me feel bad and say sorry.

He says that he feels really awkward. I told him that maybe if he went out more, the awkwardness would go away, but he still refuses. He even says that he feels awkward all the time, like he's uncomfortable in his own skin.

Is there any way I can slowly get him to socialize more? I know that I should be respecting his choices and all that, and I am, but I also know that this level of reclusion is a little unhealthy. And besides that, before I can actually get around to asking him out (because I know for sure he won't), I need to make sure he's comfortable with going out as friends.

Although, the fact that he sort of likes someone else is rather an obstacle...