The Trivial Pursuits of Arthur Banks follows successful playwright-director Arthur Banks, as he stages the latest play based on his dysfunctional life. While searching for love and success throughout the rehearsal process, Arthur turns to his therapist and his best friend Chandler for advice. Most of that advice has to do with the problems that occur every time he falls for a woman -- be it his live-in girlfriend Annette, his over-the-top leading lady Cornelia, or the lovelorn teenager Chloe.