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Living In Sin: Sexless in the City

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Sex is something that drives us, empowers us and gets us into really stupid situations with people we have no business seeing naked. Jen Sincero is the bestselling author and sexpert with the carnal knowledge you need. Ask her your questions (all are posted anonymously). Cuz there's no such thing as being too good in bed.

Dear Jen,
I apologize in advance because I’ll be using references to Sex in the City, and hopefully it won't seem as pathetic to you as it did to me while running it through my head…

I’m almost 30 years old, I lost my virginity not very long ago and have slept with that one guy only. I’ve been trying to put myself out there and have gotten a few bites here and there but nothing solid. I'm introverted and quiet, but given the right company can definitely be more social and engaging. I'm the 29 yr old, just deflowered Miranda.

Here’s a bit about two of my good friends: One is a self-described slut, which is something I’ve always admired about her. She can like someone and sleep with them, but has the ability to let go of those feelings afterwards. She's a man. Better yet, she's Samantha. She’s engaging, aggressive and very outgoing.

The other friend is a sort of an extreme version of Carrie. She’s never really been without a man by her side or in her bed, though none of those relationships seem to end particularly well. She's very flirty, sexual, open and very beautiful, and a little bit damaged, which to me, seems to be an irresistible combination. Hell, I've been sexually attracted to her and if I didn't love her so much, I'd probably hate her.

How do I find a happy medium between the two? Samantha says that I just need to tell guys that I want to sleep with them. Hard to do. Rejection and all. Carrie says that I just have to be more open and walk more like a woman (I'm more of a skinny athletic type than a voluptuous woman -- which they both are). Hard to do. I've become more open, but that fear of being hurt has definitely made things difficult, even in our friendship. How do I sleep with guy number two without getting completely shit-faced first?
- Late Bloomer

Dear Late,
I don’t know you, but perhaps the real question here isn’t how to sleep with guy number two, but rather how to sleep with girl number one. Yes? No? Maybe so? The fact that you’ve hesitated so long, have a boner for your friend, get queasy about being open with your gal pals (about what?), walk like a rodeo star and relate to dear dykey Miranda…sounds like you’re barking down the wrong pair of pants to me.

If I'm undeserving of a toaster oven and it really is man meat you crave, all I can tell you is to relax. And to remember that men are people, not just things that make you feel weird and dopey and worried that your ass is too fat. Make friends with some of them. Open yourself up and learn to trust them. Introduce yourself to the very different, very strange ways their minds work. Once you know the lay of the land, you'll be able to jump their bones on much more solid ground. A big problem about waiting so long to have sex is that it gives you more time to think about it, freak out about it and pick it apart - if you gave this much thought to, say, eating eggs, you'd be a dear caught in headlights at the omelet bar too.

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The other problem here is that it sounds like someone did a tap dance on your self-esteem and put some scary ideas about sex and intimacy in your head. Until you address these issues, it's going to be rough opening yourself up to anyone, regardless of their gender, and I think a wee bit of therapy would do you well. So would not comparing yourself to your friends anymore - you are your own fabulous, unique, sexy self, and that's what someone is going to be attracted to, not how many bells you can ring when you walk.