Lloyd Christmas and Harry Dunne are two goofy best friends living together in Providence, Rhode Island. Their homes, jobs, and love lives are absolute disasters, but they don't care until one of them, Lloyd, falls instantly in love with a Mary Swanson whom he cabs to the airport. He follows her inside and observes that she drops her briefcase. Unbeknownst to Lloyd, that briefcase contained ransom money for the kidnappers of Mary's husband, Bobby. But immediately noticing a way to her affection, Lloyd grabs the bag and races after her. He finds that her plane to Aspen, Colorado has departed, and so naturally he decides to follow her with Harry.
What ensues is a folly-filled adventure of the two men on their pursuit, being introduced to the kidnappers by way of their parakeet's decapitation, encountering tough guys that for no apparent reason attack them in a comedic fight scene in a restaurant off of the highway, and taking a wrong turn on the last leg of their trip, ending up in Nebraska instead of the desired Colorado. All this for Mary, whom Lloyd hopes can "plug them into the social pipeline."
While the movie is funny, it does not ultimately comment seriously on society. The final clip is a defeated Lloyd and Harry, who have created more trouble than they've solved. The boy and the girl do not end up together, and the men are not elevated out of their previous statuses whatsoever. They quickly disregard their failure, and begin a lighthearted game of tag, literally skipping off into the sunset. It would be a stretch to say the movie presents a serious theme of "If you have friends, you don't need anything else," because truly, the movie simply exists for the hilarity of the men's follies.