Jack (Prinze Jr.) is a thirty-something New York City advertising executive, living a life forged from routine. He is successful and stylish... and extremely bored. Jack meets Jill (Manning) by chance on a rooftop. Jill is looking for an apartment and asks Jack for directions. Jack suggests Jill's name for an ad shoot. Later he drives Jill to her apartment and realizes the neighborhood may not be all that safe. He helps Jill move out of her place and the two move in together by week's end. The pair pieces together a playful manifesto of "rules to live by." Jack's best friend and business partner, George (Stebbings), notices a more playful side to Jack's usual cynicism, and wants to meet the cause.
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