Plot
Brian Flanagan is a cocky, naïve, ambitious, charismatic, and initially shallow young man from New York City who seeks both get-rich-quick methods and the powerful status that comes with it.
Brian recently got discharged from the U.S. Army, heads home to New York, and hopes to land a high-powered business job. He fails and instead works as a bartender while attending business school.
Doug Coughlin, an experienced bartender, takes Brian under his wing and teaches him flair bartending. Doug shares his idea for a nationwide chain of bars called Cocktails & Dreams. Brian drops out of business school, and they become popular bartenders at a trendy nightclub.
Their flairing act attracts Coral, a wealthy photographer, and she and Brian start dating. Doug bets Brian that the relationship will not last and, unbeknownst to the latter, seduces Coral. When Brian finds out, he and Doug fight and dissolve their partnership.
Two years later, Brian is working at a beachside bar in Jamaica, hoping to save enough money for his own establishment. He meets artist Jordan Mooney, and they begin a passionate relationship. Doug shows up, married to the wealthy, flirtatious, and much younger Kerry, and bets Brian that he cannot attract Bonnie, a wealthy older woman. Brian accepts his challenge and wins Bonnie over. Jordan is devastated when she spots Brian and Bonnie drunkenly walking to Bonnie's hotel room. The next morning, Brian regrets the fling and seeks out Jordan, only to find that she returned to the United States.
Brian returns to New York with Bonnie, hoping her influence will help get him the corporate job. He soon feels marginalized and resents her lifestyle. While attending an art exhibit, Brian has an altercation with the artist Robert Powell in front of Bonnie's friends, leading them to break up despite her wanting to work things out.
Brian tries to reconcile with Jordan, who angrily refuses. She reveals that she is pregnant with his child and does not want him in her life, then moves into her parents’ upscale Park Avenue apartment. Jordan's father, Richard, tries to pay Brian off, but he refuses. Jordan explains that she hid her family's wealth because she wanted him to love her for herself. To prove how little he cares about money, he tears up her father's check and leaves.
Brian finds Doug on his yacht and believes he has finally achieved the financial success they both sought. However, Doug tells him that when his business began to fail, he invested all of Kerry's money in commodities and lost her entire wealth.
When Brian takes Kerry back to her apartment, she says she is bored with marriage and tries to seduce him, but he rebuffs her. He goes to Doug's boat and finds him dead from suicide. Kerry later mails Brian a letter that Doug left him, explaining that his life was a fraud.
Distraught but determined to win Jordan over, Brian tries to visit her but is stopped by security. He fights his way up to the apartment, tells Jordan about Doug's death, and says he does not want to make the same mistake by being too proud to ask for help. He says his uncle Pat has given him a loan to start his own bar. Jordan agrees to take him back, but Richard interferes, leading to a scuffle with a security guard. As they leave, Richard threatens that they are on their own.
Brian and Jordan marry. Brian achieves his goal of opening his own bar, Flanagan's Cocktails & Dreams. At the grand opening, Jordan whispers that she is expecting twins. To celebrate, and to Pat's dismay, Brian proclaims that drinks are on the house.
