Dave Hirsh (Sinatra) is an alcoholic soldier, freshly discharged from the Army. He once had a career as an author, and published two books, but drinking and writer's block have left his writing career moribund. He drinks too much one night and wakes up the next morning in a bus that has just arrived in his hometown of Parkman, Indiana, where he is making his first visit in 16 years. With him is Ginny Moorehead (MacLaine), a dim-witted but attractive and affectionate girl who has accompanied him to Parkman because she likes him and also because she is trying to escape Ray, a mobster creep who has been stalking her. Dave tries to put Ginny on a bus back to Chicago, but she sticks around.
Dave rather unwillingly meets with his older brother Frank (Kennedy), who married into wealth and now owns a prosperous jewelry shop. Dave and Frank don't particularly like each other; Dave is bitter that his older brother sent him away to a boarding school when Dave was 12, and Frank, who is cultivating the social elite in provincial Parkman, regards his brother as a social embarrassment. Frank for his part is stuck in an unhappy marriage to cold, bitter Agnes.
Frank tries to make amends with Dave for appearances' sake, but Dave isn't very interested. Nor is he interested in the adoring Ginny, who keeps hanging around. He is however very interested in gorgeous Gwen (Hyer), who admires him as an author and wants to get his career going again. Dave has another admirer in genial gambler Bama Dillert (Martin), who wants Dave, a skilled poker player, to join him in the professional gambling circuit.
- The Alcoholic:
- Dave, who's only in Parkman in the first place because he got blackout drunk and boarded a bus. When he's challenged over his request for liquor in the morning, Dave says "I don't watch a clock."
- Notably worse is Bama, who packs a whole suitcase full of liquor for a trip to Terre Haute, admits to drinking a fifth of whiskey or more a day, and is told by a doctor that his drinking has given him diabetes. After he finds this out he keeps drinking.
- Artistic License Medicine: The doctor says that alcohol adds large amounts of sugar to the blood. Alcohol in fact lowers blood glucose levels by inhibiting gluconeogenesis.
- Beer Goggles: Bama's rather uncouth statement about women and bars. "I don't know what it is about them pigs, but they always look better at night."
- Betty and Veronica: Ginny is fun-loving and she dresses sexy and she's kind of dumb and she likes to get drunk in bars. Gwen is a proper, refined schoolteacher who first appreciates Dave for his talent as a writer. Both of them fall in love with him.
- Contrived Coincidence: Dave and Bama go off on a gambling trip. Dawn skips town after finding out her father is having an affair. They wind up in the same nightclub in Terre Haute at the same time.
- Death by Adaptation: It was Frank Sinatra's idea for Ginny to be the one who is shot and killed. See Spared by the Adaptation below.
- Downer Ending: Ginny is shot and killed by Ray, with a bullet meant for Dave.
- Empathic Environment: When Dave takes Gwen into a passionate embrace in a cabin, the lighting goes dark for no reason at all.
- Hollywood Tone-Deaf: Ginny's truly horrific "singing" when the band at the bar plays a song she likes.
- Hot Teacher: The gorgeous Gwen. Dave makes a habit of calling her "teacher" in a loaded way.
- It's All About Me: Frank doesn't care about anyone but himself. He sent Dave off to boarding school years ago rather than look after him. Lampshaded when Frank complains about Dave getting into a brawl, saying "How could you do this to me?", only for Dave to shoot back with "Me me me me me, don't you ever get tired of thinking about your dull greedy self?"
- I Want My Beloved to Be Happy: Ginny tells Gwen straight up that "I want him to have what he wants, even if it's you instead of me." She also offers to leave town if Dave and Gwen are serious.
- Letting Her Hair Down: Dave taking out the pins in Gwen's hair and letting her blond locks fall down leads immediately to sex.
- The Matchmaker: Mr. French is oddly determined to get his daughter together with Dave, constantly pairing them up, urging Gwen to take Dave's call.
- Never Bareheaded: Bama always wears his hat. He sleeps with his hat.
- Parental Sexuality Squick: Dawn doesn't take it at all well after catching her father engaging in Auto Erotica with his secretary in a lover's lane.
- Professional Gambler: Bama's racket. He wants Dave to join him in his poker tours.
- Roman à Clef: In-Universe, Dave's first book was a thinly veiled autobiography. Agnes was personally insulted by what he wrote about her.
- Stalker with a Crush: Ray, who stalks Ginny from Chicago to Parkman, tries to knife Dave in an alley for dating Ginny, and comes after Dave with a gun after Dave's wedding to Ginny.
- Sexy Secretary: Edith, Frank's secretary. She's young and hot and she proves very willing when Frank makes a move on her.
- Spared by the Adaptation: In the novel Ray shoots and kills Dave. It was Sinatra's idea for Ginny to take the bullet for Dave and be killed instead.
- Taking the Bullet: Ginny takes a bullet fired by Ray, meant for Dave, and dies.
- 20 Minutes into the Past: Set in 1948, as revealed by the banner celebrating the town's centennial.
- What Did I Do Last Night?: Dave wakes up hung over in his hometown, accompanied by Ginny, with no memory of meeting her or getting on a bus.
- Writer's Block: Dave has been plagued with this for many years. As the movie opens he is struggling to break out of it with a new story.
- Your Cheating Heart: Frank cheats on his wife with his secretary.