three years later, brian has taken a job in jamaica as a bartender at a resort to raise money for his own place. he finds a romantic partner in jordan mooney, an aspiring artist and waitress that he meets on the beach. doug shows up in jamaica, now married to kerry, a wealthy woman who openly flirts with other men. doug bets brian that he couldn't "pick up" a new customer named bonnie, a wealthy older woman. brian accepts the challenge and wins bonnie over. as they go back to bonnie's room, jordan sees them. devastated, she takes a plane back to new york city.