Jack (Freddie Prinze Jr.) is a thirty-something NYC advertising exec, living a life forged from routine. He is successful and stylish... and entirely bored - until he meets Jill. Twenty-one, fiery, adorable, and possessed of nothing resembling a routine, Jill enters Jack's life like a hurricane. They meet by chance on a rooftop, and move in together by week's end. Together, they piece together a playful manifesto of "rules to live by". Jack's best friend and partner, George (Peter Stebbings), notices a more playful side to Jack's usunal cynical personality, and wants to meet the cause. But there are storm clouds, as Jill's free-spirited nature causes some friction. When her long absences go unexplained, Jack forces Jill to confess that her disappearances are a result of the treatment she needs for Cystic Fibrosis, an ultimately terminal disease. Jack is furious with Jill for violating their pact of honesty, and they break up.