Lee Simon (Kenneth Branagh) is an unsuccessful novelist who immerses himself in celebrity journalism following a midlife crisis and subsequent divorce from his insecure wife, Robin (Judy Davis) after sixteen years of marriage. As he stumbles his way through both professional encounters and sexual escapades with performers, models, and other players in the world of entertainment, Lee increasingly questions his purpose in life... Meanwhile, Robin trades her many neuroses for a makeover and a job with television producer Tony Gardella (Joe Mantegna) that leads to her own celebrity interview program. She takes advantage of numerous opportunities and ends up happy and successful.