Louis, a young teacher enamored of the age of F. Scott Fitzgerald, loses his job when he’s caught trying on a bra he finds in a campus office. He decides to go to New York City to find himself and to be a writer. He answers an ad for a housemate placed by the eccentric and opinionated Henry Harrison; an odd-couple relationship starts. Louis gets a job selling advertising for a green magazine and fancies Mary, a co-worker. He meets Henry’s neighbor, the hirsute Gershon, and Henry offers Paul schooling in the gentleman’s world of being an "extra man" – a hired companion, a gigolo – for older women. Can Louis sort out these varied worlds as well as his own expectations?