My buddy told me he is afraid to have feelings for me because his life is such a cluster fuck already and he sometimes doesn't think he deserves to be happy. I'm not sure exactly what that means.. but how can i show him there isn't anything to fear?
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This kind of sounds like classic depression; specifically when he says that he doesn't deserve to be happy. I'd work at it slowly and just be persistent that he can trust you, that you're not going anywhere and that having feelings for you is acceptable. If he really can't get over it I'd probably cut your losses and find someone else; unless you're really attached to him. Then you could work up to suggesting counseling or some behavioral analysis to see what's causing the trouble. Mental health and depression are some of the biggest issues out there; the hardest part being that most people don't want to admit they have an issue or seek treatment for it, especially males. I've personally seen a Cognitive Behavioral Therapist over some anxiety issues in the past and it took me a while to warm up to the idea of going to a "shrink" but I think it really helped.
But yeah you're call really; if you think he's worth it stick it out. If it's just some fling and you're not that involved then run for the hills and find someone more stable. Sometimes I've seen guys use this as an angle to get pity and make you want them more too. So there's that to watch out for.1