Jake gets a hole in one-and a job at the magazine-when he impresses Isabel's dad with his skill at a computer golf game. But Leo winds up in the parent trap, trying to be a father to his younger brother but unconsciously expecting him to fail.

Jake refuses to explain why he's so desperate for $100 in cash but sees an opportunity to earn it by chauffeuring around Isabel's visiting young cousin, Anne. While driving Miss Annie, though, Jake begins falling for the quiet, contemplative girl.