How do you have your first girlfriend at 30 years old! By that age you should have a couple relationships you didn't even want to be a part of that you found yourself in by accident! He went to USC for Christ sakes. You could slip and fall in the quad and get laid on your way down at that school!
To be fair, I didn't have my first bf till age 35. And the guy had never had a gf either, at age 30.
But...growing up, I was not very pretty. And, very shy/introverted (so what I lacked in looks, I didn't make up for in personality....seems like you have to have one or the other, and unfortunately, I had/have neither).
But, Dave is a decent looking dude. Gosh, he's a weirdo. But, decent looking. It surprises me that some air-headed bimbo didn't go for it, at least.