- 1 hr 43 min
This movie starts with Brian Flanagan getting off the bus. He has just ended his stint in the US Army. He's headed toward the Big Apple to pursue his dreams. Once he gets there, no company will hire him without experience. He ends up going back to college and finds a job bartending at night. He meets bartender/mentor Doug Coughlin. While bartending he meets Coral. They start fooling around. While Brian feels she is special, Doug bets him that she will be in bed with someone before the week is out. Later in the bar Coral starts kissing Doug and then Brian throws a punch. Brian quits the bar. Later you see Brian working in a bar in Jamaica. A girl runs up and needs help for her friend who passed out on the beach. Brian helps her friend out. The girl, Jordan, comes back to thank Brian for helping her friend out. While talking to Jordan, Brian hears Dougs unwelcomed voice. He tells Brian he is there on his honeymoon. Jordan and Brian end up having sex. Later at the bar, Doug bets Brian he can't land a sophisticated woman. He accepts the bet. He goes home with a wealthy older woman. Jordan sees them leaving together and leaves Jamaica. Brian messed up and tries to find Jordan in New York. He finds her and she invites him to her loft. That is where she tells him she is pregnant. Brian leaves in shock. After Brian tries to date the older woman and fails, he finds Coughlin. They go have a toast on his boat. Brian leaves and then comes back to find Coughlin had killed himself. Brian goes to find Jordan. He breaks into her parents building and confesses to her that he loves her. They fight with her parents and leave together. Months later in Brians new bar, Jordan is 9 months pregnant and whispers to Brian they are having twins. The patrons all clap!