Jake Singer, Chris Eigeman, a New York private Coventry school English teacher, tries to rekindle a relationship with Julia, but she invites him to her engagement “going-away” party, asking, > are you seeing anybody? ... I mean therapy.
Dr. Ernesto Morales, Ian Holm, a perceptive psychoanalyst, critiques Jake’s habit of apologizing through phrases like “I suppose, maybe, I guess,” and he pushes Jake to face deeper issues as he resists opening up about manners and his dead mother, all while yearning to discuss the almost non-existent sex life that followed a year without Julia.
Jake resists, even as he exchanges ideas with colleagues about literature and education, challenging the notion that literature has become irrelevant in the age of modern pharmacology. He debates with Chris about the meaning of humanism, and then he encounters Allegra Marshall, Famke Janssen, along with her eight-year-old adopted son Alex, after some potent conversations about education during which headmaster Leighton Proctor invites him to Allegra’s benefactors’ luncheon.
Meanwhile, Galgano coaches Walter Cooper to step up his basketball game. Jake counsels “ease-up,” only to be rebuked with a focus on the stats. A bout of on-court tension erupts when Walter injures a player, prompting Jake to clash with faculty colleague Bill Daniels, though Patty McPherson supports him; Proctor, however, desires fewer contradictions. Jake carries these new frustrations back to Morales, seeking some clarity.
Nervously juggling a screwdriver, Jake’s colleague Gerry Leonard warns against “Yankee firewater” before speaking at Allegra’s upper-crust gathering. Allegra tries to make Jake feel more comfortable, but Jake’s subconscious replays Morales’ counsel as he processes what’s happening. Gerry then reveals that Allegra’s wealthy husband George died from a massive cardiac embolism, which shapes Jake’s emerging concerns.
The school nurse, handling four sick children, allows Jake to take Alex home, and she nudges him toward using his imagination. Morales presses for a path to intimacy through time, patience, and facing denial, repression, and fear, insisting that Jake can be capable of love, wisdom, wealth, and sex—yet not to abandon the work of therapy.
Jake meets Julia’s ex, Steve, and her fiancé Andre, recalling the days when they dreamed of changing the world by teaching kids in Brazil, and they toast to their new lives together.
The tension between Walter and his coach ripens into a violent outburst when Walter throws a chair at Galgano, injuring Jake in the process. After stitches, Jake and Allegra become intimate. She reveals that George died before baby Emily’s “two-parent family” adoption could be finalized, and she’s dodged the final home check-up. Jake voices new doubts to Morales about Allegra’s vulnerability and his own lack of wealth, and Morales’ cynicism heightens Jake’s anger. Morales suggests a romantic gesture—a Valentine’s Day courtship for the widow—and appears again during sex, only to be interrupted by Alex asking for devil dogs and by Allegra’s mother-in-law Claire visiting.
As Jake’s life becomes a tangle of choice and obligation, his father, retired surgeon Arnold Singer, asks Allegra directly if having biological grandchildren is an option, a question that adds pressure to Jake’s decisions. An adoption mix-up surfaces when Allegra’s new maid causes confusion with the agency’s caseworker, Ms. Callucci, forcing Jake to react and to tell a lie rather than think to correct the record, jeopardizing Emily’s adoption and his relationship.
Morales argues that an ill-advised emotional involvement only brings more pain and denies the possibility of a clean break. Jake counters by declaring that Morales is “worse than my father,” and he suggests that perhaps they should both make a clean break. Morales gives an ultimatum: walk out. Jake leaves, and Arnold hands him his wedding ring, saying, “You’re my only doctor now, Dad.” Arnold counsels Jake to trust his instincts and not give up. Jake tells Callucci he intends to marry Allegra and become Emily’s father, asking for another chance, but Allegra isn’t ready to have another husband.
In the final days, Jake’s students discuss Albert Camus’ LÉtranger as they wrestle with existential questions before summer break. Allegra apologizes for blaming Jake and thanks him for speaking with Callucci; she allows Emily to stay. Yet Jake decides to depart for a London semester, explaining that he “held on to someone else for too long.” Allegra responds with a hopeful, if bittersweet, perspective: that is what love is—embracing heartbreak and bravery—then she invites him home, asking, “Take me home, please?”
