Miss Information: I haven’t slept with anyone in five years. What’s wrong with me?

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I haven't slept with anyone in five years. What's wrong with me?

Leslie Kwon

Have a question? Email Letters may be edited for length, content, and clarity.

Dear Miss Information,

Somewhere along the line between high school and college, I completely lost touch with women. I mean seriously. I had one somewhat serious girlfriend in high school (dated for a year) and numerous sexual partners. None extraordinary, none traumatic. College rolled around, and nothing improved. I graduated last year, and still have no lady friends to share a night or preferably nights with. With the exception of a single one-night stand, I have been sexless for five years. I feel broken.

I tried the online-dating thing, but nothing ever materialized; maybe I tried too hard. My friends all have girlfriends and the group is pretty isolated, so meeting people that way hasn't worked out either. I have tried broaching the topic with my older brother and close friends, and no one seems to be able to help me out. There is nothing I want more right now than to share myself with someone else. I don't need a wife, or a serious girlfriend; I just want women in my life again.

I am hopelessly out of ideas, and maybe I need a psychologist, not an advice columnist right now, but either way, I really want to work this out before I end up living a life of boredom, depression, and chronic masturbation. Please don't let it end that way. Help!

XY seeks XX

Dear XY,

I wish I had a hot tip for you about capturing the heart of a lady. "If you can catch her in a mason jar, she'll be yours forever! Just poke air holes!" or "You can win her over by answering her three riddles correctly — but be careful, because if you get one wrong, she'll shoot you with her eye-lasers." Unfortunately, women are neither toads nor laser-sphynxes, but we're also not too hard to crack.

I suspect from your tone, XY, that you're selling yourself short. You've got some things going for you (a college degree, some relationship experience, an articulate and perceptive writing style), and yet you seem defeated. That view of yourself is the problem, not you as a person. The conclusion you draw is that new relationships will somehow glue you back together, but I beg to differ. You can't expect another person to fix you. Ever. So I want to shift your focus just a bit: solidify yourself first, and the rest will get infinitely easier.

It's entirely possible that a therapist will help you with that goal. So might an introspection-based practice like yoga or meditation. So might finding and mastering a hobby, anything that gives you a new sense of your own strength: martial arts, painting, interpretive ribbon-dance, whatever. Anything that allows you to step out of your "isolated" friend group is a good idea, too. Invest in some quality cocooning time, and you'll emerge an awesome, übermenschy butterfly.

As for your love life? Simply put, people are scary-good at reading each other. If a woman so much as senses the phrase "I feel broken," she'll climb out the nearest bathroom window. But if you can solidify your sense of self, that self-reliance will project. Self-reliance is in the real world what Axe is in Axe commercials. There's no great secret to how to meet women; the real key is in convincing them that you're a badass worth knowing. Before you can convince anyone else of that, you've got to believe it yourself.

Dear Miss Info,

In the past year, my life has turned into a John Hughes movie. I became interested in this guy who made tentative advances towards me, but then rebuffed me and began dating someone else. I moped and cried for a bit, but then told myself to forget about him and move on. Just when I thought I was over him, he broke up with the girl and came to me for comfort and advice. Against my better judgment, I decided that I should be there for him as a friend. We grew very close, and he's become one of my best friends. But my latent romantic feelings towards him have inevitably begun to resurface. We kissed on one occasion, and even got to third base on another, but agreed to remain as friends after both encounters.

Still, and perhaps this is wishful thinking on my part, I think he may feel the same way about me. He's always complimenting me and saying how much he cares about me, and is visibly jealous when I talk about or interact with other guys. He's also said things like "I'll always be there for you" and "when you're upset, I'm upset." My therapist thinks he is using me as a "hollaback girl" (for lack of a better term) and that I should cut him off, but I love him and don't want to lose him. At this point, the thought of him dating someone else is almost physically painful to me. What should I do?

The Real Life Watts

Dear Real-life Watts,

Hold it. You have a therapist who uses the phrase "hollaback girl?" Does she speak entirely in misappropriated, outdated slang terms? If so, I want her number. She sounds jiggy.

In bleak, tough-love terms: not only is this guy not boyfriend material, he doesn't even seem like friend material. If he cared about you as much as he says he does, he'd change his behavior to be more respectful to your feelings and needs. Not only is he not doing that, he is holding you in limbo to ensure that you're available when he wants you to be. Big Miss Info thumbs down.

As it stands now, he's able to use you for validation, a safety net, and the occasional hook-up, and — thanks to the "we're just friends" loophole — owes you nothing in return. His terminologies are the real red flags here: phrases like "when you're upset, I'm upset" are cliché at best and manipulation-soaked at worst. His displays of jealousy aren't super-encouraging, either. Jealousy happens when someone sees a threat to the hold they have on someone or something. It's the adult equivalent of shrieking "Stop touching my Legos!", and is not an emotion of respect and equality. It's nothing to build a relationship on.

Expressing interest in another person is an intense and vulnerable thing to do, and this guy is taking advantage of your openness to doing it. Anyone who makes himself strong by keeping you weak is a leech, and not worth a second thought. Your use of phrases like "against my better judgment" signifies that you realize it, too. In short, Watts: the guy's bad news. But the therapist? Now there's a keeper.