To pursue or to be pursued, that is the question

New York is a city of firsts, and I my friends am no exception. A little over a week ago I took the plunge and decided to be the first to initiate contact after a first date. I've never done this because a) the film He's Just Not That Into You and the philosophy behind it pretty much sums up my dating code of ethics, and b) I suppose I'm a little old fashioned. Let's back track a bit so I can tell you how I got myself into such a predicament.

So I met this guy on Jdate (everyone does it here), we exchanged a couple semi-flirtatious emails and a date was arranged. Allow me to preface by saying the weekend before this date, my good friend had had a horrible online dating experience (the kind you read about in Cosmo that makes you think your freaky dates were humdrum), and that prior to leaving the house for this date, my parents gave me the don't go home with strangers spiel. Thanks mom. Anyways, I'm on this date and it's going well. He's good looking, successful and funny, albeit at points in an obnoxious way. No, I have no interest in riding his motorcycle or learning salsa, but it's not like every guy I'm meeting is the man I'm going to marry. Right? Finally, the dreaded lull in conversation occurs. That's when I blurt out: "so, is your place near here"? As soon as the words left my mouth I knew I had uttered a first date no no (well at least from a girl's perspective). The fact was I knew he lived in the neighborhood from our exchanges, however, I didn't have to get all awkward and start babbling away about how I was just making conversation and that I didn't mean it like that. He didn't seem to think it was so weird and politely offered to show me his place a mere two blocks away. What a gentleman.

After leaving the restaurant, he takes the opportunity to conveniently point out, in the event I'd forgotten, that his place is so close if I'm interested in seeing it. Instead of being cool Val, I become even more awkward and start muttering no over and over again in a manner slightly resembling turrets. Needless to say, it wasn't my finest hour. I then announce I'm going to take a cab home, and that's when he leans in and kisses me. I was SO not expecting it and unsurprisingly, I was awkward yet again. I'm on a roll. The kiss was good, a little too much tongue (haven't guys gotten the memo?) but I leave feeling confused.

Three days go by and I don't hear from him. Hmm... Is it because he expected me to come up all along and decided I wasn't worth anymore effort? In truth, I didn't get those vibes from him but then again, what do I know. Of course my friends have a logical explanation: based on my behavior, he probably has no idea I'm interested, in fact, he probably thinks I'm really NOT interested. Duh, I should totally message him. I'd never thought of it like this, but I think maybe they've got a point. I have been told by men who liked me in the past that they thought I hated them. Apparently, I'm a terrible flirt. Great. But, then I think back to all those dates where I was clearly not interested in the guys and where I thought it was so obvious, yet they STILL called. Masochists? There's that line from He's Just Not That Into You ringing in my ears: "If I guy wants to see you, he'll see you". Screw you Justin Long.

Alright, I'm in New York, it's a new year, why not message him. So three days after our date, I send him a text. It takes him over twelve hours to respond and by this point it's past midnight. My friends, I think we've just entered booty call territory, how about you? And all this from the guy who wanted me to come up, interesting... Not that most guys aren't like that, but I transgress. Anyways, the timing of his response doesn't make me feel good, au contraire -- it makes me feel pretty shitty. Not only do I now not feel wanted, but I've boosted his ego by indicating I'm still interested. But what was I expecting, if he really wanted to see me, wouldn't he have messaged me? Damn it, why did I have to try new things?!

I know this is one situation, but maybe I'm just not the pursuer type. Does that put me on par with a suburban housewife from the 1950's? Should I continue messaging guys who don't message me? Maybe next time I won't get a booty call type response? Should I stick to my beliefs? I've always thought of myself as a modern woman, but maybe not in this domain? My smart, sexy and worldly bff tells me  guys' egos need stroking just as much as girls' and it doesn't matter who pursues who because it's 2012! She's got a point, yet maybe I'm not interested in a guy whose ego needs stroking? Call me selfish, but I want all the ego stroking to be directed at me, at minimum at the start. Should I just shut-up and get out my apron and whip up some meatloaf? This is not an easy question and my friend posed an excellent question: at what point in the dating timeline does the playing field even out and do I think it's "okay" for the girl to initiate contact for say a third or fourth date? I replied by saying that it's usually clear when that point is and there's no set moment, it just boils down to a feeling.

So what do you beautiful people think about girls "pursuing" guys? Does it depend on the circumstances? I think sometimes it really does, or is it always a "no", or always a "yes"? I didn't feel good after my experience, but than again, maybe if his response had been different, I'd be out with him again and not sitting here blogging.