Lenny (Charles Grodin) and Lila (Jeanne Berlin) don't have premarital intercourse. Their hotshot courtship takes place in New York City and before they know it — they're married. On the drive to Miami for their honeymoon, the young couple sing rounds as they nervously struggle to fill in the miles along the turnpike. In bed, he sadly notes her idiosyncrasies (drawing circles on his chest, eating candy bars, talking during their love-making). She calls him a grouch but eagerly tries to please. By the time they arrive in Florida, however, Lenny has fallen out of love.
Love lost is soon love regained. A flirtatious all-American blonde called Kelly (Cybill Shepherd steps out of the Florida sunshine and into his heart. While Lila is confined to the bedroom with a terrible case of sunburn, Lenny pursues the girl of his dreams who happens to be the daughter of a rich Midwestern self-made man (Eddie Albert). After several well-planned encounters with Kelly and her family, he is ready to propose and come to Minnesota with them.
The good life now within his grasp, Lenny dumps Lila. He gives her the news over a lobster dinner in a crowded restaurant. The scene is both funny and horrific. Willing her his car, it's off to Minneapolis. There he rises to the occasion — fending off Kelly's college amours, accepting a dinner engagement with her family, and eventually convincing her father of his persistent love (he cannot be frightened or bought off). Soon it's another marriage. At the party after the ceremony, Lenny's out of his element (he had worked in a sporting good store). In the last scene, he sits on an empty couch realizing that you can fool some of the people some of the time but you can't fool yourself all of the time.
Snappy dialogue and director Elaine May's natural feel for the comic moments make The Heartbreak Kid an urbane saga. The one hitch is that our sympathy in the end rests with the heartbroken Lila — thanks to the happy/sad performance by Jeanne Berlin (Elaine May's daughter). She steals our hearts even with egg-salad on her mouth.