I'm pretty sure dating a pretty girl is what he would have wanted in the first place. He just didn't want marriage out of the gosh darn blue xDAw man they did go for the pity date angle. Was hoping they'd start at friends and then fall for their actual good points, not just "you have a normal family."
I think it's more that he finally realized that she's actually a normal person in her own right, not just some god above all who went after him for her amusement.So she has some cute side to her.
Redeemed I guess?