JACK (Freddie Prinze, Jr.) is a successful NYC advertising exec, with a life as glossy as the ads he spins. JILL (Taryn Manning) is younger and new to the city, with nothing to stand on but her fiery personality and romantic ideals. Opposites attract, and the two go from strangers to roommates to lovers at breakneck speed. Together they author a manifesto of "rules to live by." But when Jill confesses to a deep secret after a string of unexplained absences, Jack is betrayed by Jill's violation of Rule 1: Be Honest ––––-- and the two break up. Later, a mysterious bomb threat called into Jack's office offers the couple a second chance.