This is bothering me, so I have to say it.
She is not out of your league, and if you think that she is, you will never get her.
Your educated, well mannered, successful enough to afford the things you have. The only thing I can derive that makes her "out of your league", would be looks.
Looks are not everything, and if you treat her like they are, she will not want to date you for the same reason you would not want to date her if you knew all she liked about you was your money.
The person that she is matters. If you think the person that she is, is out of your league, then stop trying to date her. She deserves better. If not, then stop acting like she is out of your league.
Just go ask her out, like you would any other woman, and stop looking at her as something above your worth.
I have an extremely hot girlfriend, and she is my girlfriend because of who she is, not because she is hot. If a woman is extremely beautiful and not much else, I am out of her league.
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