Jack And Jill Vs. The World (2008)

Jack And Jill Vs. the World is the story of wealthy and highly regarded New York City advertisement executive Jack (Freddie Prinze Jr.) who meets Jill (Taryn Manning) who is new to the city and its flexible morality. The two enter a relationship together and live by a set of “rules to live by” which they actually also publish. They live happily together until Jack lies to Jill about a secret he’s kept hidden from her for some time. Jill, feeling betrayed decides to leave Jack, as he has violated one of the essential rules that they have held as the standard for their relationship.