Relationship Advice?

[kai35]

The problem is that I've been slowly, and steadily, falling for him. This came to a head a month or two ago when he texted me this;
"I don't know if it's me being conceited or immature or anything, and I'm awkward as hell asking. But we're just friends, right? If you had any legitimate romantic feelings toward me it'd be good to know. Sorry to have this conversation, but I won't be entirely comfortable until I've cleared up the ambiguity"
The message really came out of the blue for me, so I kind of freaked out. It reads more as concern than curiosity to me, so my response was to just say "Just friends as far as I know. Sorry if I've been giving awkward vibes".
His response then was "Nah, just making sure I know where we stand, so I know how to interpret you. Having that possibility in the back of my mind makes some things you say feel ambiguous"

Without knowing his age and maturity level, this could be interpreted in a number of ways. On the one hand, he may be equally apprehensive about disclosing his feelings/sexuality to you and would want to know where you stand. Your response could have been taken as a rejection of sorts, or may have de-affirmed his premonitions that you are attracted to him. He may be trying to get you to break the ice.

On the other hand, he may legitimately feel awkward about it and is trying to clear the air. It's impossible to know from where I stand.

The problem is that recently we've been drinking together a lot (by which I mean three times in the past two weeks) and during those times we've gotten a tad closer. The first time we got drunk together ended with us literally holding each other and whispering in each others ears until 6am, and the second time we played an extended game of "20" questions that seemed very much like he was leading it into talking about relationship stuff; asking what my favorite date would be, etc. He also spent a period of time lying with his head on my lap and I nearly died.

It would be very unusual for a guy to do this with someone he felt awkward around. I wouldn't even do this with another gay guy who I wasn't into, much less if I were straight and was weirded out by a guy. In other words, he's apparently not as weirded out as he's making it seem when he's sober and texting you. There's a comfort level. If he was scared of the idea that you might be attracted to him, he wouldn't put himself in this kind of situation or do these kinds of things.

That being said, some guys do enjoy cuddling with other people - male or female - and it doesn't mean they're gay.

The issue here is that I don't know whether there's any reason to bring my feelings up, considering that while I feel like something is there there's every chance he feels he made his lack of interest plain, and I'm also not sure if it's even fair to bring it up considering we're going to be moving in together - I feel like, especially if he doesn't feel the same way, it would be incredibly selfish to tell him how much I care about him, or even just ask him out, when the result of him just affirming his lack of interest would be an awkward year of living together where our friendship could be ruined...

I think you need to just come out to him. I would avoid telling him that you have feelings for him. But if you come out to him, it would be easier for him to be honest with any feelings he has for you should they exist. If he knows your gay and he still does this kind of cuddly stuff with you, then I would say he's probably interested. If he suddenly stops, then he probably is either uninterested or is straight... but at least you won't lose a friend by overwhelming him with your feelings for him. I don't know the guy, so I don't know if he would be overwhelmed. But coming out and confessing your feelings for someone at the same time can be a bit overwhelming.

Best of luck to you.