A failed playwright, Henry Harrison (Kevin Kline), develops an odd mentor relationship with Louis Ives, a troubled, cross-dressing, aspiring writer to whom Henry sublets a room in his New York apartment. Henry teaches Louis the art of being an "extra man," accompanying and entertaining wealthy older women in their fanciful social lives. Along the way, Louis encounters an environmentally conscious co-worker, Mary Powell (Katie Holmes) and a jealous, eccentric neighbour, Gershon.

Cinema Village, 22 East 12th Street and 5th Avenue, Manhattan.

Mary's Workplace, 37 West 20th Street and 6th Avenue, Manhattan.

The Russian Tea Room, 150 West 57th Street and 7th Avenue, Manhattan.