Jack and Jill vs. The World (2008)

• 43%
• 2008
• Comedy
• Romance
• Vanessa Parise
• Freddie Prinze Jr.
• Taryn Manning
• Peter Stebbings

In Manhattan, successful executive Jack is a methodical, controlled man with simple habits who works in an advertisement agency with his coworker George. While smoking a cigarette on the agency building's roof, Jack meets aspiring actress Jill who has just arrived in New York and is seeking a job. He sympathizes with her situation and gives her name to a Klubendorf commercial in the campaign promoted by his agency. When he takes Jill home, he finds that she lives in a very low-budget hotel, so he invites her to stay in the guest room of his fancy apartment for a while. Jack cheers up during her stay, and she proposes that they collaborate on a manifesto with "Be Honest" as Rule #1. However, she keeps something from Jack: she's ill with cystic fibrosis and only has a few years left. When Jack discovers her secret, he feels betrayed that she betrayed their own first rule, and they split up. But Jack soon sets out to look for Jill and bring her back.