Jack (Freddie Prinze, Jr) is a thirty-something advertising exec in New York City , living a life forged from routine. He is successful and stylish... and entirely bored - until he meets Jill (Taryn Manning). In her twenties, fiery and adorable, Jill enters Jack's life like a hurricane. They meet and instantly connect, launching into a romance. Together they write a Manifesto of Rules To Live By, beginning with Rule 1 – Be Honest. But after too many instances of Jill's disappearing, Jack forces Jill to reveal her secret.