Two bartenders (Tom Cruise and Bryan Brown) at a busy Manhattan watering hole dream of someday owning their own bars. Their lives consist of elaborate drink-mixing performances and sleeping with many of the female customers, until a fight over a woman causes the younger bartender, Brian (Cruise), to flee to Jamaica. There Brian finds true love with Jordan (Elizabeth Shue), a vacationing waitress/artist, but blows it when his materialist instincts get the better of him, and he takes up with a wealthy, older New York fashion designer (Lisa Banes). She brings him back to the city, where he lives as a kept man for a time. But realizing that love will make him happier than money, Brian seeks out Jordan and tries to win her back.