Molly (Kate Hudson) and Carl (Matt Dillon) are preparing for their wedding day in Hawaii, until Carl's friend Neil (Seth Rogen) interrupts to say that Randolph Dupree (Owen Wilson) got lost. They drive off together to pick up Dupree, who appeared to have hitched a ride with a light plane after landing on the wrong island. A day before the wedding, Molly's father, Bob Thompson (Michael Douglas), who is also CEO of the company that Carl works for, makes a toast with rude jokes about Carl, foreshadowing a conflict between the two. Later at a pre-celebration at a bar, Carl neglects Dupree to be with Molly. Carl and Dupree later make up on the beach, as Dupree apologizes for laughing at Bob's jokes. Carl and Molly get married. When Carl returns to work, at Molly's father's Thompson Land Development, he is surprised to find that Bob has promoted him to be in charge of a design he proposed, though it had been altered somewhat.