Played — Dana Davidson

When one of Ian's boys dares him to get plain-faced Kylie Winship to sleep with him in just three weeks, he thinks it'll be a breeze.  Tall and fine, with honey-colored skin and eyes, Ian is used to getting what he wants from girls.  And if he succeeds in playing Kylie, he'll be down with the most popular crew in his high school.  But this girl, who everyone considers a nobody, is turning out to be more surprising than he ever could have imagined.