A young teacher, inspired by the era of F. Scott Fitzgerald, loses his job after getting caught trying on a bra. He moves to New York City to pursue his passion for writing and becomes a housemate with an eccentric man. Louis lands a job selling ads for a magazine and develops feelings for a coworker. He navigates his new life, including a neighbor who offers to teach him how to be an "extra man" - a hired companion for older women - and must reconcile his own expectations with the diverse worlds around him.

The Extra Man
A renowned mentor navigates a talented young playwright through the luxurious lives of high-society widows in Manhattan's affluent Upper East Side.