OLD BOYFRIENDS

Dianne Cruise is a clinical psychologist who is suffering with an identity crisis and struggling with her marriage. In an attempt to learn about herself, Dianne goes on a road trip to reconnect with three of her old boyfriends.

Her first stop is in Colorado, where she appears on the set of a documentary movie that her college boyfriend, Jeff Turin is making. It's a campaign ad for a state politician. The star of the ad is Sam the Fisherman, who criticizes the political opponent for policies that lead to the pollution of streams. On the set Sam the Fisherman flirts with Cruise. After the ad has finished shooting, Cruise joins the cast and crew at a bar, where Sam attempts again to seduce Cruise, unsuccessfully. Turin and Cruise start talking, and they agree to meet again the next night in the parking lot.

They meet again the next night and return to Cruise's hotel, where they have sex. They both tell each other they are married, but Cruise later tells Turin that her husband has committed suicide. Turin then tells Cruise that his wife has left him and is living with an artist in Canada. After a brief affair, Cruise leaves without saying goodbye to Turin.

The second destination is Minneapolis, where she finds her high school boyfriend, Eric Katz, who started a formal-wear business and is in a band that plays high school dances and sad hotel lounges. She meets him by calling his business and requesting that a formal dress be dropped off for a conference she's attending. When Katz appears at her hotel room, he realizes that Cruise is his ex-girlfriend, and he invites her to see two of his shows. He attempts to seduce her but she initially refuses. After the second show, in a high school gymnasium, Cruise agrees to sleep with Katz. They drive in her muscle car to a scenic look-out. Cruise asks Katz to pretend to bully her into having sex, re-enacting an episode from their high school relationship in which he did cajole her into having sex and then subsequently bragged about it to his friends and humiliated her. While leading Katz to believe that they are about to have sex, Cruise gets Katz out of her car, and then drives away, leaving him at the look-out with no pants and avenging the earlier treatment Katz subjected her to.

Meanwhile, her college boyfriend, Turin, hires a private investigator, Art Kopple to find Cruise. While they are in Kopple's office, he makes some phone calls and finds Cruise's place of business and home address. Turin goes to the clinic where Cruise works, and is informed by her boss that she left abruptly, and that her husband, David Brinks, is still alive and did not commit suicide. Turin then visits Brinks.

Cruise's third destination is a small town, where she tries to track down her first boyfriend. She checks into a hotel across the street from the ex-boyfriend's childhood home. Cruise knocks on the door and meets her ex-boyfriend's younger brother and mother. The younger brother, Wayne Van Til (Keith Carradine), informs Cruise that her former boyfriend was killed in Vietnam.

The mother confides in Cruise that Wayne has been damaged by the death of his older brother, is still living at home, has no job and no friends.

Cruise offers to work with Wayne and help him recover from the emotional trauma of his older brother's death. Cruise and Van Til, however, become sexually involved, which has a negative effect on Wayne's emotional health and leads to his re-hospitalization. After being scolded by Wayne's mother, Cruise goes to the hospital, and meets with Van Til's psychiatrist, Dr. Hoffman. Dr. Hoffman condemns her for inflicting emotional distress on Wayne.

At the end of the film, Turin confronts Cruise at her home, and they reunite as a couple.

Dianne revisits each of her significant past relationships, confronting the wounds and truths that shaped her, and ultimately leaves each man behind on her journey toward understanding herself.

The film’s conclusion underscores Dianne’s realization that true self-knowledge cannot be found in reliving the past or seeking validation from former lovers. Instead, her odyssey through old relationships allows her to reclaim agency, accept responsibility for her choices, and move forward with a clearer perspective. The ending lands as a meditation on personal growth, regret, and the limits of nostalgia.