T.R. BASKIN

One Sunday afternoon, Jack Mitchell, a married middle-aged salesman from Utica, New York, meets his old friend, children's book author Larry Moore, while on business in Chicago. After asking if Larry knows any "girls" in town, Jack is given the phone number of T.R. Baskin, a socially isolated and sarcastic young woman who has moved to Chicago "to seek fame and fortune," in her own words. Jack calls T.R. and invites her to visit him at his hotel. T.R. arrives at the hotel, and after some awkward conversation, they finally get into bed, but Jack is unable to perform, causing her to laugh uncontrollably. She eventually begins to tell Jack about her life in Chicago up to that point, shown via flashbacks.

After flying to Chicago from Findlay, Ohio and informing her parents of her absence via telegram, T.R. first checks into a room at the local YWCA and then moves into a run-down studio apartment, as it is all she can afford. She finds employment as a typist in a large corporation, where she meets and befriends Dayle Wigoda, who arranges a double-date for them. The man she is set up with proves to be a bigot and misogynist, and after ending the date by directly insulting him, T.R. begins to spend her evenings in her apartment alone.

One night, after leaving a crowded bar, T.R. notices a man, Larry, reading a book through the window of a café. Joining him at his table, the two quickly become friendly and go back to his apartment. The two discuss their lives and regrets, and she spends the night with him. The next morning, T.R. discovers Larry has put a $20 bill in her coat pocket, having mistaken her for a sex worker. Feeling betrayed and humiliated, she runs out of his apartment and wanders the desolated early morning streets. Returning to her apartment, she calls her parents, who are implied to be furious with her decision to move to Chicago; she apologizes to them profusely and breaks down in tears.

Back in Jack's hotel room, T.R. frankly discusses the ways city life has affected her, while Jack reveals his desire to retire to small-town Florida. Jack offers to see her again, but she declines, seemingly having reached an understanding with him. The two share a friendly hug before she leaves, and T.R. walks off into the bustling Chicago streets.

The film ends with T.R. Baskin leaving the hotel, unsure whether to continue as a prostitute or change her life's direction, after a conversation with Jack about their circumstances.

The conclusion leaves T.R.'s future open, reflecting her ongoing struggle with identity, belonging, and agency. The ambiguity underscores the film's exploration of personal choice and the search for meaning in an impersonal city. T.R.'s conversation with Jack highlights the shared dissatisfaction and longing for connection that defines their lives, but ultimately, the decision about her path remains hers—a quietly radical note for a film of its era.