How do I get my brother to ask this girl out?

So my 14 year old brother has a crush at his school. He's pretty sure he doesn't stand a chance, I think he does though. She's the same age, she's like a 7-8 out of ten on the hot scale. She's really nice, laid back, she's not super popular, she has a few friends. She'll talk to just about anyone. And she's athletic. My brother could be a 5-6 if he cleaned up. He's nice, but super shy. He has a small friend group and won't talk to anyone lol. Also he's not very athletic, he could be if he tried though. Anyway my questions are does he have a chance? And my other question is how can I help him?
How do I get my brother to ask this girl out?
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