Played by Dana Davidson

A popular basketball player in high school is at a dance with his friends when they claim he isn't capable of getting any girl he wants. He bets them money that he can, but they have to choose the girl. Kylie Winship is an average girl with a skinny frame and plain face. When Ian, one of the most popular boys in school, approaches her for a date, she knows something is off. Ian soon comes to find out that getting Kylie into bed in under three weeks is not the breeze he thought it would be.