Can some one please answer!!!!?

There is a sadies hawkins dance at my skool. i wanna ask this boy i kinda sorts like [btw we kinda sorta did things but we don't talk nomore] should i ask him he's kinda a playa i'm on the fence bout it!!!!! or should i just ask a freind!!!!! oh the other thing is wat should i wear!!!! PLEASE ANSWER BOTH QUESTIONS!!!! =]