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Am I not pretty, smart, funny enough to be worth going out with more than once or twice? Are guys scared off by a girl who dates around or is willing to hit the sack too early? And how freaking early is "too" early? My self-esteem is taking a severe bruising, and there's a long, cold, lonely winter ahead.
Miserable
There's no doubt that men are freaks (sorry, fellas!). A girl puts out too soon, she's a slut; waits too long, she's a tease. It would seem to be a no-win situation, but the fact is, some days it's as though you can't walk three feet without tripping over some obnoxiously happy couple, cooing at each other over warm caffeinated beverages.
I remember being so annoyed by my couple friends and their lame-o advice. "If you'd just stop looking for it, you'll find it," they'd advise, their voices dripping pity as they snuggled closer to their one and only, so relieved to be anyone but me. Or another favorite: "You must be too picky," admittedly only uttered by people who didn't know me (or my predilection for the nearly homeless and/or substance-addicted) that well.
It appears that you're making a couple mistakes. For one thing, don't answer a guy who asks—on a second date—if you're seeing anybody else. It's none of his business, and one should always go into dating with the assumption that the other person is seeing others. Always! It may not be very romantic, but dating is like an auditioning process.
Ironically, the dudes who ask such impertinent questions are invariably the ones who'd flip out if you asked the same. The correct response is to tell him you don't feel comfortable answering questions you wouldn't feel comfortable asking. Put him on the defensive, because until you've decided if you actually like the guy, it's none of his business.
Quit handing over all the power to these mooks. Don't let them see your hand, and quit buying into the flattery. Yeah, yeah, it's great that he thinks you're gorgeous, but a man will say almost anything if it means he might get his dick wet. So take it with a grain of salt. (And bring your own condoms!) Most guys who throw charm and compliments like they've been paid for with other people's money are guys who only have one or two good nights in 'em. And once they don't get what they want (which is you butt-naked on all fours), they're gone. This doesn't mean you're not pretty or excellent; it simply means they weren't interested in anything more than a quick fuck, and you were going to take more work than they were willing to put in. Good.
Take a long look at the men you're attracted to, and instead try dating quieter, less shiny boys. I'm suggesting not that you start mining the ugly pool but that you try out guys who are sans that "sexy badness" you find so compelling. Because as you get older (unless you turn into one of those broads with a penchant for the incarcerated), you'll realize that "nice" and "kind" are highly underrated qualities in a man.
Like 'em naughty or nice? Write Dategirl at dategirl@seattleweekly.com or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.