To be honest, as to the guy in question - if you've not got the spark there, it doesn't work. A relationship can only work if both people have a vested interest in it. Believe me, when one person's into it, and the other's only there because they feel they ought to be, it makes both feel like ****e.
As to the general, 'people out of my league I want' 'people in my league I don't want' - it might just be type, and so on. First of all, who can say what attracts you to someone? It'll be their charisma, their attitude that makes them special to you, and there's no list of 'hit points' to match up. It's difficult, because everyone has their insecurities, but I guess... it's just normal?