Leo and Isabel decide to move in together, but their friends and families are, to say the least, confused, especially since the couple has known each other for just two weeks.

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.

Leo and Isabel throw a New Year's Eve bash for their friends. But the limited guest list doesn't preclude some party crashers from showing up-including Everett, Isabel's ex-fiancé.

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.