Why NOT Live Flirtatiously? (Oh. Yeah. Being Terrified Is One Good Reason.)

As I was saying, I've decided that the best thing I can possibly do to improve my dating life — now that I've cycled through all of the interested and eligible men in all of New York City on nerve.com, apparently — is to get out there and meet a new dude every week, come hell, high water, or herpes. I'm not saying I'll necessarily go on one new date a week; maybe it'll turn out I won't hit it off with some guy I introduce myself to in the line at Whole Foods, or maybe he won't be crazy about me, or whatever. I'm not going to force myself on anyone, or push it if I don't feel chemistry.

Now — not to be all anti-feminist or anything but — I'll admit that I don't necessarily think it works in a chick's favor when she approaches the guy. A few of my guy friends agree with me on that — like one who just got a deal for his first novel, whose porn-star name is Harry Berkeley. They've said that when a strange woman approaches them, it always smacks of desperation.

At the same time, an equal number of men have told me that any strange woman who approaches them scores points for being so confident and outgoing (as long as she's not a complete wacko). Many of those guys — like my very sexy friend who works at a hedge fund, porn-star name Ralph Twilight — say it's tough, always having to do the work of making the first move, and they appreciate it when someone comes along to make the whole thing a little easier.

That's encouraging, isn't it? And my personal logic goes something like this: How many times have I gone to a party and not met anyone new? A lot. And how many times have I then missed out on meeeting approximately 50 percent of the single men there who might have appreciated it if I'd talked to them? An equal number. How many relationships have I missed being in, as a result of being shy? I can't say for sure, but I think it might be fair to guess that I walked on by at least one — and that could've been the true romance I'm looking for!

So, I've decided, if it's a choice between taking the initiative and actually meeting someone new, come what may, or not taking the initiative and not meeting someone new, I might as well just give it a shot.

I'll also admit that I've done a few warm-up runs on this whole living-flirtatiously thing, and the results were decidedly ... well, mixed. But more about that at some other point soon. (Remind me, in a week or two, to tell you more if I haven't mentioned Mr. Magazine Designer, Mr. Public Defender, or Mr. Italian Novelist by then.)

One last thing: I'm really pretty terrified about this little flirtation experiment of mine. I'm not an especially confident person. I'm absurdly sensitive, in fact. My ego is about as sturdy as a wet paper towel. I take it somewhat personally if people on the subway don't smile back at me when I smile at them. (Like, what, I'm not cute enough for you?) My whole night can be ruined if some guy, at a party, moves on to one of my best girl friends after chatting me with for a while (even if he never ends up asking either of us for our number). And if I go on three or four dates with some guy who then tells me he's just not that into me, I am always convinced that means I suck so bad I'll never find anyone. So this will be a year not just of living flirtatiously. It's also going to be a year of trying to build up my own self-esteem so that I don't take every rejection, however minor, as a sign that I'm a complete failure.