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.

I have this fantasy where I’m sitting at a restaurant enjoying a lovely meal with family and/or friends and at the end of said meal, a handsome stranger walks up to me and tells me he has been unable to keep his eyes off me from the instant I entered the restaurant and he needs to see me again. The physical chemistry between us is instantaneous; my cheeks turn beet red, I smile, he smiles, and voila – I am swept off my feet by the man who will become my husband. Last Saturday, my fantasy came true, well the first part at least…

After all, if everything went according to plan, I wouldn’t be sitting here on Valentine’s eve eating chocolate cheesecake from City Bakery (amazing by the way), and sharing my love life with you people. So here’s what went down: handsome guy celebrating his birthday with a bunch of buddies comes up to me and tells me he finds me very attractive and has been trying to make eye contact with me all evening. We banter for a bit, I smile, he smiles, and he proceeds to get my number. Then, unlike many pickups prior, he asks me to schedule our next meeting right then and there. The only day we can agree on is Tuesday – aka Valentine’s Day. He makes a joke about how he won’t do anything V-day related and I laugh saying it isn’t a particularly Jewish holiday anyways. We laugh some more, stare into each other’s eyes some more and he tells me he can’t wait till Tuesday. Did I mention this guy is fineeeeeee??! He tells me to come out with his friends, but I decide to make him wait till Tuesday. Turns out I’m the one waiting.

After texting him Monday night to ask if we’re still on or if it was a figment of my drunken imagination, he replies: “Hi! Holy shit. I’m sorry. I’m really not an ass. I’ve been sick since Sunday. Saturday night I got home at 6 a.m. Been out of it since and just didn’t remember. Raincheck? It wasn’t the alcohol. It was the after effect:(“. Seriously? You just turned 31 and you can’t recover from a hangover in three days? Needless to say, the date has yet to be rescheduled.

So why am I telling you this? Mainly because writing is therapeutic and I’d rather use my blog as an outlet for my venting than say, a metal pole or a certain guy’s head. Maybe on a certain level I’m hoping to gain some insight into the opposite sex, or perhaps into myself? Yes, I knew this guy was drunk, so was I mind you, but we really did spend a large chunk of the evening having very coherent conversations and my friends can attest to that. The point is I was really excited because I rarely feel such an immediate connection and because as cynical as I may be at times, I’m still a really positive person underneath who believes in true love (most days). Plus, this guy had totally acted out my meet-cute fantasy and did I mention he was fineeeeeeee??!

After some pondering (okay, way too much pondering), I have arrived at the conclusion that the reason this date isn’t happening has nothing to do with me. The guy barely knows me so it’s not like he discovered some flaw in my personality. I also doubt it was a beer-goggles type scenario. I mean c’mon, I was wearing my one sexy outfit and five inch heels! And plus, I did actually see him looking at me all night… There are a million reasons why this date will never be. For instance, he could’ve recently broken up with a girlfriend, he could currently have a girlfriend (eww), or maybe he didn’t like me as much as he let on and just didn’t feel like going on a date. He could also be an escaped convict who was caught and escorted back to prison and they simply forgot to confiscate his cell phone. Really, you don’t agree?

When I recounted the story to my male friend, he asked me a wise question, one that I’m still pondering over. His theory is that if a guy is confident enough to walk over to a girl and tell them how attractive they find them right off the bat, it’s highly likely that guy has lots of experience doing that sort of thing and could I really see myself with a guy like that? Good point. Well, confidence is always attractive, but hitting on tons of girls and having the ego that goes with that isn’t. I guess most of us want someone who is confident with women and in other areas of life, but not to the point of cockiness, or sluttiness for that matter. Like with everything else, it’s all about that elusive balance. Sigh.

Regardless, I have no idea if this was the case with restaurant hottie, but it might just be he hits on girls for sport and once he had “conquered” me, he lost all interest. He could’ve wanted to sleep with me that very night, although that leaves me wondering why he was so persistent about scheduling a future meeting time and significantly less persistent about meeting up later that night. Anyways, it really doesn’t matter because it’s over and done with and if I’m going to continue attempting to date in the crazy city that is NYC, I have to learn to move on and not overanalyze, especially situations I’ll never have answers to. I’m working on it, okay? Next post, I’ll tell you about my foray into online dating. Let’s just say they don’t call it Zoo York for nothing…

p.s. if anyone cares to offer any insight into my “situation” please do share!