Louis is a young and intellectual prep school teacher who faces an unexpected career shift after a rather embarrassing incident involving a brassiere in the headmaster's office. Resolved to start anew, he relocates to bustling Manhattan and finds accommodation with the notably conservative Henry, a sophisticated yet eccentric older gentleman who holds the peculiar belief that women should remain uneducated.
Henry's peculiar habits, including unconventional morning routines, paint a vivid picture of his character as he expounds on his views regarding women's inferiority. Meanwhile, Louis secures a job at an environmental journal and quickly finds himself drawn to his co-worker, Mary, but she declines his advances, hinting she’s involved with someone else.
In a rather unorthodox turn of events, Henry reveals to Louis that he identifies as an escort, or an “extra man,” who provides companionship to older women without accepting monetary compensation. Living under a misconception of aristocracy despite lacking wealth, Henry insists he is no deviant. Yet, when discussing his past roommate Gershon, who had a fetish for bondage, Henry's discomfort is evident.
Out of curiosity—and perhaps a desire for discovery—Louis seeks the services of a “spankologist” to explore his own boundaries. Following Henry's advice on becoming an extra man, Louis finds himself attending an art opening where both his naiveté and Henry’s persuasion clash, leading to an awkward encounter with one of Henry’s clients.
Meanwhile, Mary invites Louis for a casual lunch, hinting at Henry’s possible feelings for him and requesting that he cover her work as she goes on vacation with her boyfriend. Amidst various social outings—including a seaside lunch with Henry and Gershon, where Henry’s sciatica flares up—Louis embarks on his next escorting venture, accompanying the spirited Vivian to a lavish dinner party where he unintentionally offends someone connected to Henry.
As winter drags on, Henry departs for Florida, leaving Louis to grapple with his growing discontent. When Otto, a former roommate of Henry’s, comes back into the picture, Louis navigates an identity crisis, experimenting with cross-dressing only to realize it isn’t suitable for him.
This realization coincides with Henry's return due to a family tragedy, leading to a confrontation where Louis is compelled to leave. After a tumultuous night on the streets wondering about his job security, he surprisingly receives a promotion from his boss. Upon reuniting with Henry, tensions ease, and as the trio attends Otto's wedding, they discover unexpected twists regarding the bride’s age and other future prospects. The experiences continue to intertwine their lives in a revealing journey of self-discovery and societal dynamics.
