Advice

Miss Information

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How do I show women I'm attracted to them without being creepy?

Dear Miss Info,

I'm a mid-twenties straight guy in a big city. Growing up, I was doughy and acne-covered, super-duper-sweet, and insecure. Nobody wanted to date me. Now I'm hot and muscled, no acne, kind of intense, still a little insecure. Still nobody wants to date me! It's making me rather unhappy.

I'm a pretty interesting and socially aware dude, and I actually get a lot of positive attention from women nowadays. I don't grope women, whistle at them, pop my collar, act or look super "jock-y," or do any other obvious dealbreakers. I have female friends, regularly have normal non-sexual conversations with women, and smile frequently. Essentially I am totally not a creeper (and more modest and less douchey in person).

My problem is that women I'm interested in end up being so mean to me that it hurts my feelings. Sooner or later they run away or don't want to go out again or fail to show up or start ignoring me like a diseased homeless person. And I never understand why. I didn't do or say anything inappropriate! I just turned on the sex vibes.

So now the essential question: how the hell do I convey (without saying it, of course) that I am a tough, confident badass who is awesome in the sack and simultaneously a sweet, gentle protector who isn't going to hurt her and just wants to snuggle? And then, after lots and lots of rejection that doesn't match people's perception of me, how the hell do I still feel desirable and confident enough to dust myself off and do it over and over again? And then, because every woman is different, how do I tell how much of tough and tender to express for each circumstance?

— Hot, Intense, Possible Douche?

Dear Dear HIPD,

The good news is, I see no huge red flags in your letter. (Except "turn on the sex vibes." What does that mean? Is that like switching on the red light over your circular bed?) But here's my working theory: is it possible that your years as a dorky wallflower have followed you into a hot body? It seems like you're spending so much time analyzing each move that you're unable to just "be."

If you came of age as a highly perceptive, hovering guy in headgear, you might continue to see yourself that way, even now that you're fun and cute. So, when you get rejected in the present, it kicks you back to when you were at a sixth-grade dance, standing alone by the snack table and wondering how all the popular kids got their hair so shiny. So you assume that the problem must be you, and you assume — like many loners — that thinking and observing must be the way out of it. It's a trap, though — overthinking everything kept you in the corner as a kid, and it will continue to keep you removed as an adult. (Incidentally, there is no shame in this. Many fantastic adults were forged from periods of orthodontia.)

My point is, HIPD, analysis only gets you so far. You can't engineer yourself into the ideal man through careful calculations. In this case, your letter is so focused on yourself and your movements that I get very little sense of who these girls are. How are they all mean to you? Where are you meeting them? Try not to lose sight of the fact that any interaction is a fifty-fifty kind of deal, so if it is going down in flames, that's not necessarily a failure of yours. And if she's a jerk to you, that's her failing you, not the other way around.

In short, don't bother playing the lengthy chess-game you seem to have set out for yourself: "Am I too intense? Better counter it with aloofness. Oops, that was too sexual — better mention how much I enjoy commitment." Girls can pick up on that Jekyll-and-Hyde conversation, and many of them will walk away from it. It sounds like you've got a pretty good head on your shoulders — now just tell that head to shut the hell up. Behave in whatever way seems most authentic to you, and I think you'll find that you attract similarly authentic people.

Dear Miss Info,

Recently my girlfriend and I have been wanting to take our relationship to new levels sexually, and we are unsure how to proceed. I guess the logical next step would be anal play from both of us, but the idea makes me uncomfortable. On the one hand, I'm afraid it'll hurt her, and on the other, I don't know if I'm exactly comfortable with her sticking a finger in my ass. Do other people do these things? Is it normal? What are some other things we can try?

— Seeking New Frontiers

Dear Seeking New Frontiers,

Anal sex can be a big technical undertaking, not to mention physically stressful or painful if one or both partners aren't in the right mindset — and given your ambivalence, I'm not sure you're in the right mindset. It would be one thing if either you or she were exceptionally turned on by the concept, but if you're both approaching it from a sense of, "Well, I guess we should," then don't bother. If you are uncomfortable in any way, shape, or form, you aren't going to enjoy it. So drift away from that plan, and find kinks and experiences that do turn you on.

As for what people "normally" do — eh, there is no "normal." That is to say that "normal" equals "by committee," which equals "milquetoast and boring." Have a long conversation with your girlfriend: "So, what turns you on?" Start the dialogue and keep an open mind. You may have some swings and misses, but at least you'll be trying new things.

Overall, remember that there is no linearity to sex; nothing is "worth" more than anything else. The most advanced sex is not the most acrobatic or the most boundary-pushing, but rather the kind that is satisfying to both partners.