We've been close friends for a long time now and he recently confessed to having feelings for me which I thought was great because I like him too. He acts like he's totally head over heels in love with me but he doesn't seem like he's comfortable with the idea of kissing and we haven't really done anything sexual at all. I brought this up with him and he said he's just not comfortable doing those things. When we kiss I can tell he's not really feeling it and we've never really done anything more than that. I asked him why he's not comfortable and he says he doesn't know, this is just the way he is. I know he's never had a girlfriend in the past (he's 22) and he doesn't watch p*rn or anything. What do you think the deal is?
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It sounds to me, as has been pointed out, that he has some issues. They are most likely psychological and he'll need some help from a pro to get them worked out. Might be a couples counseling thing but I doubt it. It could also be he has a physical issue he hasn't disclosed. I feel like you do indeed need to tell him you want to be close and that includes a happy, healthy physical relationship and that if he needs to get some help to get there with you, you'll support him anyway you can. Don't settle for a situation where he's gritting his teeth while you go down on him and dreads when it's time to have sex. Good luck and let us know what happens.1