Jack (Freddie Prinze Jr.) is a 30-something New York City advertising executive. He is successful, stylish... and extremely bored. Until he meets Jill (Taryn Manning). They meet by chance on a rooftop, and by the end of the week, they've moved in together. Together they piece together a playful manifesto of "rules to live by" and things are definitely looking up. However, Jill's free-spirit starts to cause some friction—especially when her long absences go unexplained. Jack forces her to come clean and she confesses that her disappearances are a result of the treatment she needs for a serious illness. Jack is furious with her for violating their pact of honesty and they break up. However, Jack has underestimated his feelings for Jill and seeks to find her... but is it just too late?