How often do you have to talk to someone to ask them to a formal?

[che che]

I really like this kid that goes to my brother school but the thing is 1. he is kind of a player but I still can't get over him (believe me I have tried) 2. I never see him 3. He is one of my parent's old friends son so it would be awkward. But basically I really want to ask him to this dance, but like I said I never really talk to him because we are both shy. I don't know how I can start talking to him more often so asking him to my Soph Hop wouldn't be weird or should I just randomly text him one day and ask him? I'm so confused and any help would be greatly appreciated.