I am a heterosexual female and I have a gay best friend...whom I've recently developed a small crush on. It's actually really annoying, but it's not like I can really control who I'm attracted to. I feel we both connect on a much deeper level and I'm pretty darn sure he feels the same way, too. We tend to have the most fun when it's only us alone hanging out. Which is when he tends to say 'off' things, things I don't expect to be part of his nature. For instance, he expressed to me that he would totally bed a certain, very beautiful, voluptuous actress (says it about other girls as well). Then, again, if someone had the chance to sleep with someone extremely beautiful and famous, wouldn't you take advantage of that opportunity? Another time, we were under the influence of a substance and he sort of insinuated something sexual. He said that if in that moment, a hand happened to touch his nether region, he wouldn't brush it away. Stuff that makes me think, seems to always happen. He said something about how he can't have sex with men cause it hurts... Is it possible he's conflicted about his sexuality and wants to venture out?
Many times he has expressed his dislike for the gay community and the individuals that sustain it. Although, it's not like he represses his homosexuality. He is very much 'out' and makes everyone aware of that fact. As I gazed further into your blog, I came across the bits of 'internalized homophobia.' This sounds like a more likely scenario than if he were to actually be sexually attracted to me, right? Maybe it's just me, being a girl, wanting something she can't have. Or my overactive imagination putting in work... but I don't think those comments/actions are exactly 'normal' for a gay man is it? Either way I want to move on and I don't want to ask him straight out. I would much rather avoid any awkward confrontations, which would probably spoil the friendship. What's your take on this matter?
My take is that your friend is essentially what we call a "self-hating homo." Any openly gay man who expresses disdain for the gay community is clearly dealing with issues about his sexual orientation. Sadly, there are many gay men who are openly gay but for one reason or another are not happy being gay, largely because they've swallowed society's negative opinions about gay men. or they may have religious hang-ups or feel that being gay makes them "unmanly" -- or just have a basic insecurity about themselves. Then there are people in every minority group who have simply had unhappy or unsuccessful lives for one reason or another and make their race or religion or sexual orientation the reason, unwilling to face their own flaws.
Without saying that your friend may be "bisexual," being gay does not mean that a man finds women repulsive or can't have sex with a woman. [Many married homosexual men sleep while their wives while dreaming of being in bed with guys.] And sure, some gay men might get a kick out of sleeping with a famous female celebrity -- although they'll still be gay in the morning. But be careful of things expressed while under the influence, as they should never be taken seriously.
As for his comment that it "hurts" to have sex with men, I can only assume he's a bottom and a rather inexperienced one at that. Either he can try being a top [or eschew analism altogether] or he can get more experience.
Frankly, this guy may be your bmf, but I think it would be a mistake on your part to expect more. Even if the two of you indulge in some sexual fooling around, it may not lead to anything realistically romantic or permanent. Guys like this often try to "go straight" or become "ex-gays," but while they may get married and even have kids, they remain homosexual. And why would any woman want a homosexual husband?
Some time you might ask him how he feels about being gay and ever so delicately suggest he get counseling or therapy. He can't change his orientation, but he can certainly learn to accept and enjoy it.