Miss Information

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Is my boyfriend allowed to sleep with other girls if they're lesbians? Because he thinks he is.

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Dear Miss Information,

My boyfriend and I have been dating for about three months, and have been very happy. He's a sweet, charismatic guy and, as such, has quite a few female friends. I understand this, and do my best to hold back the jealousy monster and let him have time with them. But today he told me one of his friends who's a lesbian asked him to have sex with her, because she had a bad experience when she was younger. He told me she wanted to face that nightmare with somebody she trusts. He didn't give her an answer, and instead came to me.

I was a little put off that he didn't immediately tell her no, because our relationship has always been exclusive, even when we were in the first stages of dating. I then responded that I would much prefer that he tell her no, then asked what he would say if the situation was reversed, and I wanted to sleep with a gay man. His response? "Yeah, I'd let you. Why not?"

This also caught me very off-guard, so I asked why. He said, "They would have no real interest." I don't really see how that matters; to me, sex is sex regardless of sexual orientation or interest. I feel like him doing anything more than what's acceptable in the bounds of friendship is cheating, regardless of the girl's sexual orientation. Ultimately, I told him how upset I was, and he turned her down.

While I'm happy that he didn't push the issue, it still bothers me that he would even have to ask. Part of me thinks that he can't possibly really care for me while still seriously considering sleeping with another woman. And yet another part of me says it's still early in the relationship and I'm freaking out more than I should, and I just need to calm down. Shouldn't I be happy that he understood it would make me upset and told her no?

So I'm torn: am I crazy? Is that the same as cheating? And do I have a right to be upset that he was willing to sleep with her, and would be okay with me sleeping with another guy as long as he was gay?

— Flabbergasted

Dear Flabbergasted,

Any sexual activity that happens outside of the bounds of your relationship counts as cheating. By "bounds," I mean "rules you both agree upon." By definition, one's first priority in an relationship should be one's partner — and, by extension, the expectations they set with that partner. You're uncomfortable, so it's cheating. Case closed.

But this also raises some baffling points. What is this other girl doing, propositioning an unavailable guy? And, no, her gayness does not act as a force field: sex is sex, regardless of how she wants her eggs the morning after. Which brings us to your boyfriend's impressive cluelessness regarding human sexuality. The words "gay," "straight," and "bi" are shorthand that we as English-speakers have settled on to express points in a complicated matrix. They're approximations, not definitions.

Ultimately, though, intention (i.e. "It's fine because she's gay!" or "This got way less okay now I know she's bi") is way less important than boundaries. Why does she think she can step in on your relationship without causing damage? And why does your boyfriend seemingly agree with her? She is absolutely allowed to explore the edges of her own sexuality — but not if it infringes on commitments her would-be partner has made to someone else.

Lastly, Flabbergasted, have some faith in your own convictions. Many things about this situation are "crazy," but your reaction is least among them. Don't be so quick to assume you're the one who just doesn't get it.

Dear Miss Information,

I'm a twenty-one-year-old virgin who's never been in any sort of relationship and is dying to be touched/loved by a man. I have a great amount of self-esteem (I'm attractive, intelligent, and funny, with a generous dose of awkward that makes me accessible to the populace), but no one seems to be knocking at my door! I've tried everything (clubs, bars, friends, class, art shows), but I've never been asked on a date except by the random homeless fellow at the bus stop. I'm starting to wonder if it's me.

I will admit that for the past year and a half, I've been pining for a man who will never want me. I've finally accepted this and have since moved on, with no results. I hoped that this was the reason for my lonely nights — that I was giving off a "do not approach me" vibe — but still I'm alone.

I've read numerous advice blogs that suggest I stop forcing the issue, and I have for the most part. I'm working on improving myself, I'm excelling at my full-time job this summer, and I even made straight A's last semester. But lately I worry that what I'm truly doing is turning myself into a hermit, that I'm disappearing from the world and forcing myself into a solitude of self-doubt and insecurity. I don't believe in waiting for a man to come sweep me off my feet, but my active pursuit of the other sex has also done nothing for me.

I've listened to all the cliched advice. I go out with friends, hang out at places that I like, do things that I love, but I always come home wondering why I'm alone. I know in my heart that I'm a good person — honest, real, and kind — so it makes my eyes water and fingers ache to realize that nobody wants me. Do you think it's me? Am I just making excuses to be alone? Or is there a secret on how to meet a guy who I'm interested in who's also interested in me?

— College Virgin Impatient for Love

Dear College Virgin,

As a thought experiment, let's reverse the roles. Imagine the last party you went to. Who were the guys who caught your attention? Were they the ones already surrounded by friends who seemed in their element? Or were they the ones who laughed too hard, talked too much, or seemed over-eager for human contact? This is my column, so I get to answer for you. $10 says you were lusting after the former. Who wouldn't? Desperate hoverers are the worst! (Let she who has not been a desperate hoverer be the first to throw stones, of course.)

For a dose of bummer, I'm reminded of a Nick Hornby quote, from his novel How to Be Good: "Love, it turns out, is as undemocratic as money, so it accumulates around people who have plenty of it already: the sane, the healthy, the lovable." I scribbled that in my journal (I know) when I was a teenager, struck by the poetic unfairness of it all. From a safe distance, I can call a qualified "bullshit" on it. That line is the voice of a narrator, not the voice of God. I was not destined to be alone at seventeen. You are not destined to be alone at twenty-one. But that line does speak some truth. It sounds like you've already got a lot of love accumulated around you — it's just not the specific type you're looking for.

So how to you earn more love? By playing up how lovable you already are. (Hat tip, Hornby.) The best way to do this is to stop trying. Go to art shows… because you like the art. Hang out with friends… because you like their company. Be open, but don't chase. You should find that removing ulterior motives does wonders: stay present where you are, not pining over what you don't have. All of your relationships should improve — present ones as well as future ones.

Also remember that each of us has our own timetable. Don't rush into something because you feel some unseen clock ticking, and please, please don't compare yourself to anyone. You can be a badass thirty-year-old virgin, just like you can be a killer twenty-five-year-old mom; it's about owning your particular experience with grace and style. You've got nobody to answer to but the publisher of your future memoirs.