One Sunday afternoon, Jack Mitchell Peter Boyle, a married middle-aged salesman from Utica, New York, meets his old friend, Larry Moore James Caan, a children's book author, while on business in Chicago. After asking if Larry knows any “girls” in town, Jack is given the phone number of T.R. Baskin Candice Bergen, a socially isolated and sarcastic young woman who has moved to Chicago “to seek fame and fortune,” in her own words. Jack calls her and invites her to visit him at his hotel. T.R. arrives, and after some awkward conversation, they finally get into bed, but Jack is unable to perform, causing her to laugh uncontrollably. She gradually opens up and begins to tell Jack about her life in Chicago up to that point, a story that unfolds through a series of flashbacks.
Earlier, T.R. flies to Chicago from Findlay, Ohio, informing her parents of her absence via telegram. She checks into a room at the YWCA, then moves into a run-down studio apartment because it’s all she can afford. She finds work as a typist in a large corporation, where she befriends Dayle Wigoda [Marcia Rodd], who sets up a double-date for them. The man she’s paired with proves to be a bigot and misogynist, and after she ends the date by insulting him, T.R. begins to spend her evenings in her apartment alone, nursing a growing sense of isolation.
One night, after leaving a crowded bar, T.R. spots a man, Larry Moore, reading a book through the window of a café. She joins him at his table, and the two quickly establish a connection, sharing stories of their regrets and disappointments as they move back to his apartment. They spend the night together, but the morning after brings a sting of humiliation: Larry has slipped a $20 bill into her coat pocket, mistakenly assuming she is a sex worker. Feeling betrayed and exposed, she darts from his apartment and wanders the desolate early-morning streets. Back in her own apartment, she calls her parents, who are apparently furious about her choice to move to Chicago; she apologizes and breaks down in tears.
When she and Jack reunite in his hotel room, T.R. speaks candidly about how city life has shaped her, while Jack reveals his own wish to retire to small-town Florida. He suggests they could see each other again, but she declines, offering only a warm, genuine hug. As she steps back into the pulsing life of Chicago, she walks out into the city’s bustle, carrying with her the memory of a day that forced both to reckon with desire, disappointment, and the perilous lure of a new start.
