Charley Pearl (Baldwin) is the heir to a toothpaste empire's fortune engaged to be married to the daughter of a Hollywood studio mogul, whose best friends accompany him on a drive to Las Vegas for his bachelor's party. They make a quick stop for a drink at a nightclub where Vicki Anderson (Basinger), a glamorous singer, immediately disrupts Charley's thoughts of wedded bliss. He tries to pick up Vicki after her performance but is sternly warned that she belongs to somebody else. Vicki responds to Charley's charm, however, and obligingly offers to leave a window open at her home. Charley shows up and they end up in bed, only to be caught in the act by her other loverBugsy Siegel, the notorious gangster.
Rather than react violently, Bugsy amuses himself with the notion that he will take the scared-stiff Vicki and Charley to a justice of the peace in the middle of the night and make them marry one another. After the marriage becomes public and the subsequent scandaly, Charley and Vicki agree to get an annulment, but unbeknownst to them, this wouldn't be the last time they met — or marry, for that matter.
This film features examples of:
- Distracted from Death: Played for Laughs. Charley's father is dying and Charley flies back to Boston to see him before he dies. He brings his new wife Vicki with him so his father can finally meet her. However, when they get to Boston the father is so sick that he is unconscious most of the time. They wait by his bedside hopping for him to regain consciousness one more time so he can give them his blessing. After hours of waiting Vicki has to go to the bathroom really bad. As soon as she starts to leave the room, the father seems to wake up. She rushes back but it proves to be nothing. This happens multiple times and Vicki finally can't wait any longer and runs to the bathroom. Right after she left, the father woke up, spoke his final words to Charley and then died shortly before she came back.
- Divorce Is Temporary: Taken to extremes when Charley ends up marrying Vicki four times.
- In Love with the Gangster's Girl: Charley ends up sleeping with Vicki, who turns out to be the girlfriend of the notorious gangster Bugsy Siegel. Uncharacteristically, the gangster is a good sport about this and rather than having the couple killed, he has them marry each other.
- Serial Spouse: The movie centers on a couple who married each other and then divorced multiple times over the span of decades. By the end of the movie they are about to get married for the fourth time.
- Shotgun Wedding: Bugsy Siegel decides to inflict some ironic punishment on Charley and Vicki by forcing them to marry each other.