Based on his play by the same name, Neil LaBute's script follows a successful writer who, on the eve of his wedding, travels across the country to meet up with ex-lovers in an attempt to make amends for past relationship transgressions. Crisscrossing from Seattle to Boston, he reunites with high school sweetheart Sam, sexually free-spirited Tyler, married college professor Lindsay, his best friend's little sister Reggie, and "the one that got away" Bobbi. A modern-day Candide stumbling through a landscape familiar to most men-messy breakups.

Bored with Bollywood movies but fascinated with their Hollywood counterparts from his youth, Ram dreams to become a singer and actor in America, the country where dreams are made. He is encouraged when his American-based close friend, Vijay Rao, comes for visit, and brags about driving a Mercedes and living in a penthouse. The Guptas do their best to talk Ramu out of going to America, but in vain. Ram does travel to America and upon arrival in New York is received by Vijay. This is where Ram will get a shock when he finds out that Vijay works as a waiter in an Indian Restaurant, drives a taxi-cab for a living, has never owned any car, and lives in a small apartment based in a Cinema Theater that hosts Bollywood movies, and his two room-mates are Sanjeev and Amit, one of them an illegal immigrant. Ram gets a job as a waiter in the same restaurant as Vijay, but is fired when he gets into a physical argument with a customer...