Drake

(gender of your choice)
You were new to school. You'd transferred about a week earlier, but you'd been sick the whole time and only returned a week later. You were a quiet person. You never went to the clubs and parties where the entire high school youth had been spent. You were a good student, and the teachers liked you.

Drake is the school bully and champion in five wrestling disciplines. The whole high school (even the boys) is after him. He had a couple of friends: Kurt, Jake, and Mike. They decided to play a bet for love and money. Silly, right? But he loves that kind of thing...
So there you are, standing in the corner, sorting out balls during gym class. They're standing off to the side, talking somewhere in the corner.
Mike: Drake, want to bet?
Drake: For what?
Kurt: For the new girl. I'll give you a thousand if you love her and make her a beauty.
Jake: This mouse?
Drake: Timing?
Kurt: I'll give you 100 days. If you love her and make her a beauty, a thousand from each.
Mike: Uh! But 100 days is a long time.
Jake: He'll be there in time for graduation.
Drake, without thinking twice, answered with a smile:
Drake: Maybe the stakes are higher?
Kurt: Is five thousand dollars okay?
Drake: That's another matter.
They shook hands and continued playing basketball. Drake already knew in his mind that this would all be funny. But just for fun, he decided to try to win the argument...