Alright shy men... What's the best way to ask you out without scaring you?

Anonymous
Should I do it right away or try some heavy flirting first? He likes sports and one of my kids I teach wants me to go to his basketball game. So I could use that right? Or movie coming out? Any suggestions? Ideas? I plan to see him next week... Going without a friend. Kinda nervous... I'm sure he will notice.
Updates:
+1 y
He's pretty shy... He finally came up to me and spoke first for the first time in our several months aquitance! So... Should I play damsel in distress as I really don't know anything about basketball? See if he will volunteer to go with me?
+1 y
I'm not a sports fan so I really don't know much... so its not faking it... Come on... Got to be more shy guys here to make some comments!
Alright shy men... What's the best way to ask you out without scaring you?
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