Jesse Fisher, Josh Radnor is a 35-year-old college admissions officer in NYC who loves literature and language, and lately feels restless, discontented, and stuck in a life he didn’t quite plan. He clings to the memory of his happiest days at an unnamed Ohio liberal arts college, a place where study felt uninterrupted and surrounded him with kindred spirits. When his former English professor, Peter Hoberg, invites him back to the campus to attend a retirement ceremony, Jesse’s nostalgia is stirred and he accepts the invitation, hoping to reconnect with the past even as his present feels precarious.
On the eve of the retirement events, Jesse encounters Zibby, a 19-year-old drama major and the daughter of Peter’s friends. Zibby, Elizabeth Olsen immediately piques his curiosity, and their initial meeting kindles a tentative spark. After the retirement dinner, a campus party provides another fateful crossroad: Jesse and Zibby run into each other again, sparking a plan to meet for coffee the following day. The two spend the afternoon wandering across the campus, swapping thoughts on life, books, and music, while Jesse revisits the old thrill of a conversation-rich connection that feels almost like a second adolescence. In the mix of familiar faces, he also crosses paths with Judith Fairfield, Judith Fairfield, Elizabeth Reaser a former romantics teacher he deeply admired, and he meets Nat, as well as a brilliant but troubled student named Dean, who, like Jesse, always carries a book with him.
From this point, a correspondence grows: Zibby asks to keep in touch through handwritten letters, and the two begin to tread the delicate boundary between mentorship, affection, and infatuation. Meanwhile, Peter grapples with the unsettling prospect of retirement and the possibility that his legacy might not unfold as he planned; he even seeks to extend his time at the college by appealing to the Dean, only to be told that a replacement has already been hired. The dynamic on campus grows more tangled as Zibby invites Jesse to return to the grounds, hinting at her blossoming feelings for him. Jesse, aware of the significant 16-year age difference, agrees to see where things might lead, reflecting on the chasm between youth’s eagerness and maturity’s responsibilities.
As their relationship deepens, Jesse and Zibby share moments of closeness and affection, including a kiss, but the realities of their ages and life paths weigh on him. When Peter notices the affair, he urges Jesse to pursue relationships with women his own age, a well-meaning push toward realism that underscores the film’s broader meditation on growth and responsibility. Zibby confesses her feelings and even asks to sleep with him; Jesse hesitates, and his decision hardens after she reveals she is a virgin. The revelation hurts Zibby and she asks him to leave, leaving Jesse to navigate the aftermath.
In the wake of this disruption, Jesse seeks solace at a bar, where he reconnects with Judith Fairfield for a one-night encounter. The moment is charged and complicated, and afterward Judith urges him to mature beyond his past patterns, ultimately sending him away. Meanwhile, Zibby attends a party and shares a kiss with a classmate, a moment that signals the widening gap between their hopes and the realities of their separate paths. Jesse departs, choosing not to see Zibby again at that moment, but he does bid farewell to Peter before returning to New York.
Back in the city, months pass, and Jesse writes to Zibby with a new tone of apology and reflection. He acknowledges the hurt caused, explains that the experience helped him grow, and reveals that he has begun dating Ana, a bookseller closer to his own age who shares his passion for literature. In a pivotal turn, Jesse helps prevent Dean from acting on a dangerous impulse tied to his own despair, encouraging him to stop retreating into books and to reengage with life.
The story moves toward a reconciliation as Jesse reaches out to Zibby again, offering a sincere apology and explaining that he values what they shared while recognizing that a shortcut to life through a relationship would not be right. Zibby responds with a nuanced understanding, admitting that part of her desire was to leap forward, but acknowledging that the relationship’s restraint and timing were, in the end, for the best. The film closes with a quiet, hopeful image: Zibby lying down to read Songs of Innocence and of Experience, the book arriving by courier from Jesse, while Ana rests on Jesse’s chest, both couples conversing softly about growing old and the ways love and literature shape a life lived with intention.
