Dating Actuarially

I'm having a bourbon and decided I'd throw a curve ball and write a post about dating.  As a single mid-20 something recently broken up from a long term relationship, I'm becoming increasingly aware of my own shelf life as a bachelor and how this is at odds with the lifestyle (exams) I've chosen for the next 5 or so years.

At the end of April I broke up with my girlfriend of about a year.  She was a childhood friend/flame with whom I had reconnected last summer.  At the time, I was in school and we lived 3 hours apart.  The fact that we saw each other about every 3 weeks or so along with the fact that I was an impoverished, returned-college student while she was 5 years into a very successful career in finance made the relationship difficult (moreso for me than for her, of course).  As I approached graduation with only one job offer in hand (from my current employer) and that location being equally as far away from her, it became clear things were not going to work out between us.

So with that background, I re-entered the 20-something dating scene.  By "scene" I largely mean online dating...I've been around long enough to have noticed the trend, which is that if you go up and talk to a girl in person out in public these days you are automatically a creep (which was not the case 5 years ago).  I think this coincides with other increasingly anti-social trends among youth - probably due to the influence of technology and weakened bonds within communities with each passing generation.  Or maybe I'm just growing uglier as I get older, I don't know...

That said, I've had a *couple* dates since graduating in May with girls I've met in person, and in fact 0 dates from online dating sites.  But I've spent more time trying to meet girls through the sites.  I think this is a second observation - if you message a girl on an online dating site, you are automatically a creep and must be ignored.  I know - girls are inundated with messages from every slob out there once they log on.  It is also possible I am in fact coming off more and more as a creep (desperation?) as time passes, leading to greater rejection.  I would think I'd have better success as a reasonably good looking, intelligent, and charismatic guy *with a decent job*.  Anyway, just venting a bit...

Well, I know it hasn't been long and I'm meditating to cease looking and to instead allow opportunities to come to me (and to recognize them).  I'm extremely picky with looks and personality to start, so I can't help but think about how the eligible female pool is dwindling with a constant force as t --> ∞.  I wonder if my x is thinking the same as I am but about men.  Maybe we will revisit each other at 30.