yeah man I hear you. I am similar to you in the way that you've been told your good looking before and had some popularity in highschool. It sounds like your a respectable dude. I mean I try to take care of myself too and when I compare myself to other guys, I see myself as someone girls SHOULD be interested in. When finally some interest is shown I find myself saying something seen as stupid too, it sucks.
When I look around at my friends who all have had at least one girlfriend in their lives and I've had none, I ask what's so great about them and not me?
The only logical answer I can come up with is nothing, in fact, in a lot of ways I'm better than them. Im taller with a semi-muscular build, better looking, getting a university education, have money, play sports. I see myself as this well rounded person and the only thing holding me back from getting a girl is I don't pursue girls and show perseverance.
I think thats all there is to it i think. Perseverance. Lots of girls want a boy in their life, thats it. Yeah they know they want him to be smart, funny, rich, handsome, whatever, having those is a plus. Girls love attention so I think by showing some in them and pursuing them is a good bet to get some interest in you. Cause I've been trying to make it work without pursuing, its the only thing I know how to do, and have had virtually no success.
Hopefully you don't get the vibe that I'm trying to tell you how to live your life. Just someone who has had similar experiences and knows what its like to obviously be a great catch but is somehow overlooked.