The Extra Man (2010)
A man who escorts wealthy widows in New York's Upper East Side takes a young aspiring playwright under his wing.
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?
- Louis is a young bookish prep school teacher who is relieved of his job after accidentally handling a brassiere in the headmaster's office. He soon relocates to Manhattan and moves into a room with Henry, a greying but handsome older man who is so conservative that he feels women should not be educated.
Henry is a wildly eccentric sort, dancing in bizarre morning rituals that belie his age and lecturing Louis on the inferiority of women. Louis finds a job at an environmental journal where he is immediately attracted to his co-worker Mary.
Henry explains to Louis that he is an escort, a walker, an extra man, and most certainly not a gigolo because he does not take money for his services in entertaining older ladies. He also lives under the delusion that he is an "aristocrat" even though he has no wealth. Louis asks out Mary and she declines, suggesting she is seeing someone else.
Louis responds to an ad from a middle-aged female "spankologist" whom he pays for treatment. Without knowing this, Henry tells Louis that he kicked out his last roommate, Gershon, because he was fascinated with bondage. Henry proclaims he is himself not a sexual deviant in any way, but refuses to elaborate when Louis asks him more specific questions. When Louis sees that Gershon is a sullen hirsute local, Henry claims he tried to help Gershon over his deviance, and agrees to try training Louis in becoming an extra man.
Henry takes Louis to an art opening and introduces him to a potential client as well as one of his own, but the evening turns sour when she tells him she will not need his services for her annual Palm Beach vacation.
Mary invites Louis out on a casual lunch date and, in addition to suggesting that Henry may be in love with him, she asks him to cover some of her work while she goes to Jamaica with her boyfriend.
Henry invites Louis out for a blustery seaside lunch with Gershon, who speaks in a squeaky high-pitched voice. The trio go for a walk on the shore and while Henry tries to show Louis how to dance he aggravates his sciatica.
Out of commission in pain, Henry sends Louis on his next extra man job. Louis escorts spirited granddame Vivian to a fancy dinner with six other guests, where he accidentally insults a man who turns out to be Henry's protégé. Vivian likes him even more when he brings her home and carries her to bed, to sleep.
Later that night, Henry leaves by bus to rest in Florida for the next few months. Louis grows dour over the winter months. One day Henry's former roommate Otto returns, who will be marrying Vivian's granddaughter, and they make small talk.
Louis, who had tried some cross dressing with his spankologist, visits a tranny bar and soon hires a helper to remodel him into a woman specifically one who looks like Mary. The result makes Louis realize that cross-dressing is not for him.
At the moment of this realization, Henry happens to return home due to Vivian's death, discovers Louis dressed as a woman, and angrily tells him to leave.
The next morning, after crashing his car and spending the night on the street, Louis fears that he will lose his job, but his boss actually offers him a promotion. Louis returns to Henry that afternoon, who is not so angry at him after all. Gershon emerges clean-shaven with a haircut and returns a play to Henry that he had stolen from him.
The trio attend Otto's wedding, where his bride turns out to be a little older than him.