When Jack Mitchell (Peter Boyle), a married middle-aged salesman with children from Utica, New York, meets his old friend Larry Moore while on business in Chicago, he asks him if he knows any prostitutes Jack can date while in town. Larry gives Jack T.R. Baskin's phone number, and Jack invites T.R to visit him at his hotel. T.R. arrives at the hotel and is relieved when Jack is impotent and cannot have sex, and she begins to tell Jack about her time so far in Chicago, a story that unfolds via flashback.
After flying to Chicago from Findley, Ohio, T.R. first checks into a room at the YWCA and eventually rents a studio apartment in a dilapidated building in a run-down area of the city. She finds employment as a typist in a large corporation where she meets and befriends Dayle Wigoda (Marcia Rodd), who arranges a double-date for them. The man she is set up with proves to be a bigot and misogynist. T.R. realizes she'd rather be alone than spend time with such a callous individual. T.R meets other individuals at her job and becomes more affiliated with the city but seems uninterested in her surroundings.
One night, after leaving a noisy bar, T.R. sees a man reading a book at the window in a café. She joins him at his table and learns his name is Larry and he edits and publishes books. The two become friendly and go back to his apartment to discuss their lives. Larry is divorced and misses spending time with his children, while T.R. confesses she always has felt like an outsider. The two have sex, and the next morning T.R. feels she finally has taken the first step towards an intimate relationship, only to discover Larry has put a $20 bill in her coat pocket and mistaken her for a prostitute. Feeling betrayed and humiliated, she rushes out and walks the streets of Chicago contemplating what just happened while a voiceover of her saying that something "clicked" in her mind about what she wants to do with her life. Once she arrives at home, T.R. calls her parents to apologize for leaving home without telling them and has a breakdown.
Back in the hotel, T.R and Jack discuss their current situations; why Jack is cheating on his wife with a prostitute, and why T.R is one. T.R tells Jack that she was tired of working as a typist and needed more excitement in her life and the two agree they are glad they met. The film ends with T.R leaving the hotel debating about whether she should continue being a prostitute or not and what she should do with her life.
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