The Gawker commentary around a NY Times profile around 'literary manboys' seems to describe me quite well. Glad to know that I'm not the only one like this.

And an enlightening comment that seems to fit me pretty well:

I know men(boys) like this, albeit much younger. I would argue that the woman from Saipan was not "the one who got away," but one in a string of examples of women who are, for whatever reason, unavailable or otherwise not dateable.

People like this are really into self-sabotage. And they will never change. No matter how much you might delude yourself into thinking otherwise over the course of two years.