Ya know what's funny? That guy is very likely to end up with the girl he wants.
Women will take the confidence and success over the looks in a heartbeat.
They are not as shallow as men.
The only woman that would take him is a gold digger after his money, IF he actually really has a lot.
I think anyone can end up with the person they want, no matter what they are, if they're willing to pay for it one way or another.