› firstname.lastname@example.org 
I have a very close gay male friend who often behaves like he's interested in me romantically. He has even told me that he gets crushes on girls, that 1 percent of him likes women, and that he's gotten semihard from girls three different times. He often gazes at me while we're talking as if he's thinking of kissing me. Even my friends notice. He also tells me that I brought happiness back to him and that he feels alive when he's with me. We spend every other night together talking and flirting till 5 a.m.
I don't need a boyfriend. Even just a kiss or sex with him would be fine with me. I find him attractive, and nothing we would do would ever dissolve our friendship. I once told him in a lighthearted manner that if he ever wanted to do something, I was up for it. He gave a vague response.
How do I approach this without offending him? I'm kinda shy about these things. Also, he is over 30, so he is not in a phase. He is very open about his homosexuality.
Friend of Friend of Dorothy
Semihard three times in 30 years! Well, that is persuasive.
I have a gay forever-friend who always said that someday he'd marry me, and damned if he didn't — he became a rabbi and officiated at my wedding. You've got to admit that's something of an exceptional circumstance though.
I'm glad that you say there's no romantic interest here, since I'd hate to have to shake my head sadly at you. I'm going to pretend to believe you instead, although I think you are interested in him ("My friends say he likes me!") and I think he's gay. Really, really gay. The kind of gay that's so gay it doesn't matter if he "gets crushes" on girls or even if he has sex with one. He's still gonna like boys, and he's still not going to "like" you like that. None of which means he doesn't love you and consider you his soul mate and think you're pretty. I've no doubt he does. But if you went so far as to proposition him directly and got a "vague response," well, he already said no. He just didn't want to hurt your feelings when he did it, because he loves you. And is so, so gay.
Do you think there's a real chance of a long-term relationship between someone who identifies himself as "maybe poly" and someone who is pretty sure she's monogamous to the core? It's a great relationship even with this business, but I feel like I need some kind of resolution. He's already passed up one opportunity for sex with a long-standing (very poly) friend of his, which made me feel better on the one hand and guilty on the other.
I'm reading about polyamory and looking at it like the trained, rational scientist I am. I can accept it without wanting to embrace the lifestyle myself, but there are times when the whole thing just seems designed to aggravate my insecurities and turn me into a grasping, clingy girlfriend.
I don't have a problem with the "other close relationships" thing. I just seem to have a problem with the sex. Is this cultural indoctrination, as the books would have it, or a real concern?
What makes you think they're mutually exclusive? Wanting your lover all to yourself is certainly culturally supported, if not precisely a matter of indoctrination, and it's also perfectly natural. It's a bit like hetero- or homosexuality in that you can cross over and act "as if," but if you have a natural inclination toward monogamy, it's going to be a poor fit: too tight, and itchy to boot. One ignores such discomfort at one's peril.
It's nice that you have what you term a great relationship with Poly Dude, but you do realize that at this point it's functioning as something of a three-way — you, your boyfriend, and the elephant in the room? You're going to have to talk about this eventually: Is being poly part of his core identity? (It rather sounds not, which is good.) If he does feel the need to experiment, can your relationship withstand the stresses, and can you withstand the temptation to throw things at him? Even more important, can you forswear wallowing in guilt for something you did not do and were in fact powerless to affect in any way? If so, great — go forth and pursue whatever it is you hope to pursue with Semipoly Dude. If you answered "no" to any but the first of my too many questions, then your relationship, lovely as it is, is fated to be brief and end either badly later or amicably now. So I hope you didn't.