As of yesterday I’ve now met 34 women off the internet since December 2012.

Though it’s possible to overthink things and see patterns where none exist, there’s two kinda counterintuitive conclusions I’ve drawn from my experiences.

One is that I have struck out with every woman who I’ve met for a first date that I initially found highly attractive, and the other is that the women I’ve ultimately found most compelling and affecting – Kristina, Elle, Rachael, Kyla – are women who I wasn’t initially sure I was that physically attracted to. Those four caused me way more heartache than the beautiful women I met and missed out on after merely one date.

Let’s talk about the first phenomenon: the women who were stunning at first glance who never end up liking me. Regrettably that’s happened to me at least five or six times. The simplest explanation for this would just be that maybe the super hot women have really high standards and that I didn’t measure up to their expectations. I’m sure this was true to an extent for some of them, but I don’t think it’s fully persuasive because my profile had and has a lot of pictures of me, including both facial closeups and full body shots. If I wasn’t even in the ballpark of attractiveness for them, presumably they wouldn’t have agreed to meet in the first place. (First time users may make the mistake of rolling the dice by agreeing to meet people who are “maybes” from a physical perspective, but I get the distinct sense from my own experience and talking to power-dating friends that just about everyone who’s taken a couple laps around the internet love block gets more and more particular about risking their precious dating energies on people that may show up looking closer in proximity to negative numbers than double digits on the ol’ 10 point scale, if they (the lap-takers) can possibly help it.)

At first I responded to setbacks with the hyperbeautiful by trying to hit the gym, improving my wardrobe, and reflecting upon the style of hair on my head or on my face. Now though, I think addressing the issue is trickier than just getting to be the hottest I could possibly be.

I’m convinced now that I unwittingly treat women I’m really attracted to in ways that make me unappealing. In The Pale King, David Foster Wallace described the effect a beautiful woman had on the men around her and his analysis rings true – that extreme beauty “raises the stakes” and makes it hard to be yourself, be engaging, just be human to the person you’re meeting. This is, of course, super self-defeating.

Without question I did this on the date I had with Grace, the first women I met off the internet. In her profile pictures she’d been heart-rendingly pretty and she lived up to that description in the flesh. Carried away with my own good fortune and desire to impress, I talked a mile a minute and told her about a wide variety of the many facets of the gem that is my personality and as you can imagine, I came off as needy and self-absorbed – a combination few people hammer out on the keyboard in response to the “What I’m Looking For:” prompt on the dating sites.

Conversely, the four women I’ve met out of 34 that I feel most fondly toward – each of whom I’d jump at the chance to date again – all were cute but not initially incredibly gorgeous to me. My first date with Kristina lasted 6 hours of unbroken conversation in one coffee shop, Elle 17 hours at four different locations followed by spending the night at her place, Rachael 8 hours that concluded when we made out in front of her house, and Kyla 5 hours, three of which consisted of sitting on one park bench sharing pretty intimate confidences about love and loss. And all agreed to second dates. Though ironically, it’s only now in retrospect that my desire for each of them is strong. At the time I was up for a second date, but I wasn’t gunning hard to get with any of them.

I was hoping that the process of writing this post would shed some light on how to succeed in dating people you’re really interested in, but I don’t think I’ve succeeded. Since the realization that how I behave around powerfully attractive women makes me less likely to connect with them, I’ve tried to harness that knowledge and adjust my attitude when I find myself getting carried away, but thinking to myself “don’t think of how hot this person is” ends up tending to psyche me out rather than bolster the self-assured well-adjusted demeanor that would be truly beneficial.

Oh well.