A few weeks ago, I blogged about a night on the town with Rob Barnum, who heads up Cyan + Long Tail’s West Coast office, and who had ostensibly come to New York to get some film-related work done.

Instead, that week our best work took place out of the office, on Friday night, at a succession of West Village bars. There, we spun variations on a yarn about being blimp racers that was so over-the-top I couldn’t believe it consistently and repeatedly worked in picking up women.

Sure, I’d long believed that the secret to the bar scene is quickly and positively differentiating yourself from the slew of generic lotharios working their best “come here often?” lines. But I had never before pushed so deep into the realm of the ridiculous in the process, and never before seen such effortless results.

So, in the middle of last week, I decided I’d take things up yet another few notches. Which led me, at a bar near Gramercy Park, to instigate and referee a rock-paper-scissors tournament between two groups of attractive women.

I tried it again in Boston this past Friday night, with girls so jadedly halter-topped as to preclude nearly any other approach, and was stunned to find the ploy again worked flawlessly.

At a subsequent bar, I inked out a tic-tac-toe game on the back of a napkin, and requested the waitress deliver it to a group of girls at the far end of the bar. I told the waitress to deliver it circuitously, though, and to bring the napkin back and forth, between moves, surreptitiously enough to keep my identity as anonymous challenger secret as long as possible.

Which worked, in short, even better than rock-paper-scissors, and culminated in numbers not only from two of my amused adversaries, but from the intervening waitress as well, who tucked hers in alongside the bill.

Still, I’m not sure if I’ll have the chance to give any of them a call; I’ll be too busy working up my Yahtzee game and Rubik’s Cube skills. If tic-tac-toe works well, then either of those should absolutely kill.

Tallying in a recent revelation, I’m now up to six.

Six girls I’ve dated, that is, who, in the last twelve months, have gotten married or engaged.

Apparently, a few months with me, and you can’t possibly wait to get out of the singles scene for good.

But, on the plus side, as my mother points out, I could likely leverage that into a solid side-business: dating unhappily single New York women, who could then move on and rather instantly get hitched.

More ammunition for my family and friends’ ongoing ribbing:

As she’s been spending more evenings at my apartment in the last couple of weeks than there’s even vague precedent for in my dating past, for Valentine’s Day, I gave The Girl a toothbrush.

Now, seeing it sitting next to mine in the sink-side cup, I alternate between smiling like an idiot and thinking that if I turn into the kind of guy sappy enough to not just grin at a toothbrush but actually blog about it that I’ll basically have to kick my own ass.

As the last few posts have led friends and readers to question whether I’m losing my sanity, or at least my asshole edge, I should add briefly that, despite any of many upsides to this girl and her friends, last night also did leave me feeling even deeper entrenched in a ten-years-younger reenactment of a Sex and the City episode.

Which is, perhaps, unavoidable if the girl you’re dating is paid by an online magazine to write (in great detail) about her dating life, but even moreso if, when you meet her closest friends, you discover that they consist of a confident go-getting Samantha, a shy, conservative Charlotte (who, in at least one photo snapped late in the evening, rather strikingly resembles Kristin Davis), and a cynical gay best-friend Stanford (who, fortunately for the real life version, is far better looking than the television equivalent).

I suppose that, in turn, makes me rather inevitable; every Sex-in-the-City story needs an (interested yet historically completely emotionally unavailable) Mr. Big.

Since, if I don’t write something about it, I’m going to get about fifty emails asking:

The second date was even better than the first.

[Further details once I figure out what to say that won’t come across like a thirteen-year old girl’s gushing IM’s to her friends.]

Came up to Boston for the weekend, to see one of my closest friends and his wife and to squeeze in a quick investor meeting. And, on the train up Friday afternoon, I started to write a post about the trip that also obliquely referenced my date the night before. What I started writing was short on detail because, I told myself, I didn’t want to kiss and tell. But, in fact, it was short on detail because I was worried what my date would think if I wrote what I was really thinking, and worried what other people would think if I wrote what I was really thinking.

Realizing that’s a long, long way from the sort of damn-the-torpedoes full-speed-ahead radical honesty I’ve been trying to stumble my way through for the last year, I instead – wisely or not – scrapped that post and decided to just lay it on the line. So:

I went on a drinks date Thursday evening that was good enough to become a breakfast date Friday morning and good enough to justify me totally violating my usual rule for minimum time between first and second dates by asking to see her again this Monday night. I’ve spent the weekend sort of secretly terrified that she’s going to cancel the second date, which, on the one hand, I’m pretty sure she isn’t, but, on the other, probably means I’m far more interested than my commitment-phobic conscious brain would otherwise acknowledge. And while, obviously, after just one date it’s impossible to say where this might go, it’s the first date I’ve been on for a while where I’m at least exceedingly excited to find out.

Usually, I stick closely to the Roadies’ Rule: no heavy drinking on consecutive nights. I seem to have lost sight of that entirely this week, waking up and swearing off liquor each of the past four mornings.

And while that would normally leave me scrapping my evening plans, instead I’m heading out once again tonight, this time to one of my favorite tacky-chic bars, more nervously excited than I should probably admit.