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Go visit some of his games. Congratulate him after one or two but not all. Come with one of your friends one time and after he wins (losing may put him in a bad mood and he would be more likely to say no) go up to him and say something like " good job! (boy says thanks) then you ask him out to somewhere, to hang out sometime, or just plain ask him out. Good luck :)

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Q: How do you ask out a boy on the baseball team?
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