Anyone have outofleague syndrome?

[Pink Floyd]

There is nothing wrong with this unless you are developing heavy self esteem issues as a result of being rejected. But it sounds to me like you are a prideful person, with very much confidence. Try using those skills for other things, rather than just women. It will take you far in life if you choose to make the best of it in that way. And I say you've got a shot at that girl. Be yourself, (assuming you're a nice person) and lead up to the big question. There's nothing wrong with that at all.