I am a straight 23-year-old woman. My super cool 21-year-old ex-boyfriend—who is really fun and has a ton of gay friends—kind of gives off a gay vibe. He has a gay brother and a kind of homophobic family. (His family doesn't even know his brother is gay even though his brother has been with his partner for years.) We were in a relationship for nine months, and while our sex life was very affectionate, it wasn't super sexy. He was always pretty interested in trying anal play, because he likes the feeling of not being in power, and he is attracted to muscular male arms. (I get this. Me too!) I tried do it for him—anal—but he wasn't really that into it when we did it.

After we broke up he told me he would be interested in having a man penetrate him anally. I said, "Gosh! I'm so glad that you trust me so much to tell me this! You're an attractive guy, and I'm sure tons of guys would love to penetrate you anally! Do you think that maybe you might be gay?" He said he wasn't gay and that for some reason he had trouble getting guys into him. He says he is annoyed that not enough gay men hit on him. (Duh. Because you tell everyone you are straight!)

I really enjoy having sex with both men and women, and I wouldn't want to invalidate someone else's bisexual life experiences/orientation/identity. Also, we're both sort of submissive, so perhaps we had bad sex was because of that and not because he's gay. (You should also know: I am his first girlfriend and first sex partner ever, other than a somewhat non-consensual relationship he had as a teenager with an older woman.) But when I asked if he was bi he said no! He says he's straight but that he wants another man's dick up his ass. (He used other words.) Again, Dan, he has of gay friends and his only close family member is gay. If he's really gay, he should be out by now. I'm out as bi and have been since before we met.

Sometimes when we hang out it feels like he wants to get back together. For example, he asked if we could get back together. I love being close to him, but I honestly have no desire to have sex with him, and I was very honest about not wanting to get back together. The worst part is, I don't know whether or not I'm allowed to hang out with him anymore. He said he wanted to get back together and I should probably avoid him so as not to lead him on. On the other hand, he sounds pretty gay, and I'm one of the only friends he has told about that aspect of his sexual orientation, meaning I should be around to support him if he eventually comes out as gay. Also, I really like him! He's so cool! It would be super convenient if he were gay, because then I could have no guilt about hanging with him. What should I do about this?

Cute Boy's Ex-Girlfriend

My response after the jump...

I don't wanna commit an act of bisexual erasure here, CBEG, because that'll gas up the "Dan Savage is a monstrous biphobic meanie" thing. But I'm thinking your ex-boyfriend is gay.

It's not the wants-to-be-anally-penetrated-by-a-man thing or the obsessed-with-muscular-male arms thing or the making-out-with-other-dudes-at-parties thing that leads me to believe he's gay. Lots of bisexual dudes want to be anally penetrated by other dudes and obsess about muscular dude arms and make out with other dudes at parties. No, CBEG, what leads me to believe that he's gay is... paradoxically...

Your ex-boyfriend insists he's straight. Nothing but straight.

Insisting you're nothing but straight while you're talking with your ex-girlfriend about your burning desire to be fucked in the ass by another man—not being willing to cop to bisexual or even heteroflexible—is some pretty twisted gay fucking closet case shit. Add the homophobic family and the out-to-him-but-not-to-the-homophobic-folks brother and his desire to get back together with you despite the less-than-spectacular sex life you two had together.... and you're lookin' at the psych profile of a deeply conflicted totally gay 'mo. Why not a deeply conflicted totally bi bi? Because if your ex were bisexual, CBEG, he would probably be able to say that—at least to you—because "bi" doesn't preclude winding up in a relationship that would meet with his family's approval. But because he's not bisexual... he can't bring himself to say anything at all.

Well, anything other than "I want to be fucked in the ass by another dude." He can say that. But that's about an act, not an identity. He's making a distinction between those two things—between acts and identities—which is pretty common in the deeply conflicted totally gay 'mo community.

I could continue to unpack this for you, CBEG, but your question wasn't, "Is my ex-boyfriend gay?", but rather, "Should I hang out with my ex-boyfriend?" And my answer to that is yes. Your ex needs a confidant, he needs someone he can be open with about his heterosexuality, and the clear benefit of your being there to draw him out—gently helping him see the contradictions?—far outweighs the small risk of your hurting him by leading on. What he needs is a gurrrrlfriend, not a girlfriend, and you can safely play that role for him.