After serving in the U.S. Army, Brian Flanagan visits his Uncle Pat’s bar in an outer borough of New York City. Pat offers Brian a job, but Brian plans to pursue a more prestigious line of work in Manhattan. Despite being optimistic, Brian’s job search proves fruitless due to his lack of education and experience. After numerous failed job interviews, Brian notices a “help wanted” sign in the window of a Manhattan bar and wanders inside. There, he meets Doug Coughlin, a charismatic Australian who hires Brian on the spot. At first, Brian is overwhelmed by incessant drink orders in the crowded bar, but, with Doug’s guidance, he becomes more adept. In addition to teaching bottle tricks and flashy pouring skills, Doug offers life lessons he refers to as “Coughlin’s Laws.” Brian enrolls at a city college to study business, but his late hours at the bar interfere with school, and his performance quickly declines. Becoming disillusioned with school, he spends more time drinking with Doug, who says he lives on “cocktails and dreams.” Brian decides “Cocktails & Dreams” is a good name for a bar and suggests they open their own business together. One night, while performing tricks to a rowdy group of drinkers, Brian and Doug are recruited by a nightclub owner, who offers them jobs at his nightclub, “Cell Block.” There, Brian catches the attention of Coral, a successful photographer, and they begin dating. Formulating a business plan for Cocktails & Dreams, Brian tells Doug they can save the money they need by taking lucrative bartending jobs in Jamaica; however, Doug refuses to leave New York. Doubting Coral is single, Doug bets Brian fifty dollars she will sleep with another man by the end of the week. The next time Coral comes to Cell Block, Doug kisses her at the bar while Brian watches in disgust. Although Doug claims to have saved his friend from a bad relationship, Brian punches him and storms out. Sometime later, Brian tends bar at a beachside resort in Jamaica. When Jordan Mooney, a beautiful young guest, asks for Brian’s help, he follows her to the beach where her friend, Dulcy, has passed out from drinking in the sun. Brian calls an ambulance, and Jordan later returns to the bar to thank him. At the same time, Doug appears and playfully warns Jordan to stay away from Brian. Shocked to see his old mentor, Brian is further surprised to learn he has married Kerry, a beautiful millionaire. That night, Brian and Jordan join Doug and Kerry at a nightclub. As the married couple dances, Brian tells Jordan that Kerry must have married Doug to anger her rich parents. As Jordan and Brian spend the next few days together, she reveals she is an artist who pays her bills by waiting tables, and Brian discusses his entrepreneurial desires. Soon after Brian and Jordan make love, Doug returns to the bar and teases Brian about his poor choices in women, betting Brian could never attract someone as smart and rich as Kerry. Pointing out a rich woman at the bar, Doug bets fifty dollars he cannot seduce her. Brian takes the bet and flirts with the woman, a haughty New Yorker named Bonnie. Later that night, Jordan arrives but stops short when she sees Brian leaving with Bonnie. The next day, Brian looks for Jordan, but Dulcy says she flew home early. Doug offers Brian a job at a new bar he is opening in New York, but Brian already has plans to work for Bonnie. Doug suspects Brian still has feelings for Jordan and bets an expensive bottle of brandy that he will be working for him by Saint Patrick’s Day. Returning to New York, Brian moves into Bonnie’s apartment. Although she has promised him a job, Bonnie says it may take six months. Dressed in a new suit she has purchased for him, Brian attends an art opening for Bonnie’s sculptor friend but loses his temper when Bonnie ignores him and the sculptor insults him. The men engage in a fistfight, and Brian breaks up with Bonnie. He goes to the deli where Jordan waits tables and begs her forgiveness. Although she pours food all over him, Brian comes back later that night and accompanies Jordan to her apartment. There, he admits he was “spooked” by their whirlwind romance, but Jordan bets she can spook him again and announces she is pregnant. Confirming the baby is his, Jordan sends Brian away. Returning to beg for forgiveness a second time, Brian discovers that Jordan is not home. He tracks her to her parents’ penthouse apartment on Park Avenue, discovering Jordan comes from a rich family after all. She is not home when he arrives, but Jordan’s father, Richard, introduces himself and tells Brian his daughter is not allowed to marry a bartender. Although Mr. Mooney bribes him to go away with a $10,000 check, Brian refuses the money. Appearing in the doorway, Jordan accuses Brian of being too obsessed with money to care about her and denies him a second chance. He goes to Doug’s new bar to accept the job offer that was made in Jamaica, bringing the expensive bottle of brandy Doug wagered. At the bar, Kerry greets Brian with a sensual kiss and he watches as she does the same with another man. Doug leads Brian to his boat, docked behind the bar, and reveals he lost all his money in the stock market but Kerry does not know. Guzzling the brandy, Doug passes out, and Brian agrees to drive Kerry home. There, she kisses Brian, but he rejects her advances. Returning to Doug’s boat, Brian finds Doug lying face down in a pool of blood. After Doug's funeral, Brian receives a letter Doug left behind, explaining why he killed himself and describing Brian as his only friend. Brian goes back to the Mooneys’ penthouse and forces his way inside. Declaring his love for Jordan, he asks her to marry him and announces plans to open his own bar. Mr. Mooney tries to intervene, but Jordan leaves with Brian. Soon after, they celebrate their wedding, and Brian opens Cocktails & Dreams. There, he delivers a poem addressed to his unborn child from atop the bar, and promises Jordan he will never get spooked again. Suggesting she can spook him once more, Jordan reveals she is carrying twins and Brian offers a round of drink to his patrons.