A talented New York bartender takes a job at a bar in Jamaica and falls in love.
After leaving the United States Army and moving to New York City, Brian Flanagan (Cruise) gets a part-time job as a bartender at while studying for a business degree (which he needs to get a job in marketing). At first, Brian is a terrible bartender, revealed in a montage of his screw ups. Over time, he learns the tricks of the trade including flairing from his boss/mentor Doug Coughlin (Bryan Brown). Brian and Doug soon become very close; Doug readily assumes a mentor role over the young and naive Brian, and rains advice and opinions down upon him. His advice takes a familiar structure as he usually begins most of them with "Coughlin's Law". An example of his expert advice, which actually turns out to be quite poignant, is "Coughlin's Law: Drink or be gone!" Other pearls include: "Bury the dead, they stink up the joint." and "Anything else is always something better."
While Brian has high personal aspirations, Doug is leery of the notion of starting their own bar together. Doug intends to call his bar "Cocktails & Dreams".
Eventually, Brian and Doug's bar-tending act becomes popular and they end up working at a trendy nightclub catering to New York's wealthy and elite, the type of establishment where yuppies spout poetry from the top of the rafters for all patrons to hear. As their popularity rises, Brian becomes the focus of attention from a sultry brunette named Coral (Gina Gershon). Quickly, they elevate their friendship into a wild sexual relationship. During a free throw shooting competition where Brian hits five free throws in a row, Doug bets him Coral will leave him by week's end, essentially doubting there is anything special about the seemingly perfect relationship shared between the two. Unbeknownst to Brian, Doug lies to Coral about secrets being shared by Brian about her, and secures his bet by bedding the hot brunette. Brian is very upset and fights with Doug at work, essentially ending his informal partnership with Doug.
Brian, taking advice from his former girlfriend, takes a job in Jamaica as a bartender to raise money for his own place. He finds a romantic partner in Jordan Mooney (Elisabeth Shue). Jordan is an aspiring artist and waitress in New York. She and Brian spend romantic times together, playing in the water, before making passionate love on the beach by a campfire. Prior to this however, Doug has shown up in Jamaica, now married to Kerry (Kelly Lynch), a wealthy woman who openly flirts with other men and wears Tarzan-like bikinis. Doug quickly asserts himself and bets Brian to be the first to sleep with a barfly named Bonnie (Lisa Banes), a wealthy older woman. Jordan catches Brian without being seen and, devastated, takes an overnight plane back home.
With Jordan flying back to New York, Brian decides to "upstage" Doug and return to New York with the cougar-esque Bonnie under the auspices that he will be placed high up in her company due to their romantic attachment. Brian becomes impatient as the pay-off is too slow. They have a blow-up during an art exhibition where Brian gets into a fight with the artist. As they cut ties, Brian, displaying wisdom one can only assume has been gleaned from his former mentor, states: "All things end badly. Otherwise they wouldn't end!"
Brian then seeks out Jordan. Much to his surprise, Brian learns that she is pregnant with his child. He embarks on a journey to win over the independent Jordan and prove to her that, despite being just a lowly bartender, he would make a worthy father. While pursuing Jordan, Brian also learns that her family is very wealthy, and he goes to her parents' Park Avenue penthouse to speak with Jordan. Unhappy with the situation, Jordan's father, Richard (Laurence Luckinbill), attempts to buy Brian off. Brian is forced to decide between the money offered which would surely help him get his bar started versus a life with Jordan and his child; Brian refuses the money. Jordan keeps her distance, not wanting to be hurt again.
Brian meets up with Doug. Despite
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