Hailey is a conceited, professional woman and self-proclaimed serial dater with no interest in marriage. She believes no one man can possess all five of her most coveted qualities. She dates different men who possess diverse qualities, until she meets the one guy who seemingly has it all.

During the course of an ordinary week in Hollywood, movie producer Ben must navigate his way through shark-infested waters as he struggles to complete his latest projects. A demanding studio boss demands extensive changes to a movie starring Sean Penn, while another chief won't greenlight a project unless star Bruce Willis shaves his beard. Meanwhile, Ben tries to reconcile with his wife and maintain a relationship with his young daughter.

A struggling songwriter named Dave Seville finds success when he comes across a trio of singing chipmunks: mischievous leader Alvin, brainy Simon, and chubby, impressionable Theodore.