Gray e Sam são irmãos tão compatíveis e inseparáveis, que as pessoas pensam que eles são um casal. Mortificados, os dois concordam que precisam sair e procurar por um amor. Ele procurará um rapaz para ela e ela uma garota para ele. Mas quando Sam encontra sua companheira perfeita em Charlie, a vida de Gray torna-se confusa.

Two down on their luck childhood friends struggle to figure out their lives. Ray a drummer in a rock and roll band, and Owen an aspiring film maker spend most of their time working menial jobs and drinking. When Owen's fiancé Lynn breaks off their engagement he finds himself spiraling, and allows Ray to come along with him to a two bit film festival he has been invited to in Kansas. There Owen makes several attempts to patch up his relationship, while Ray scams them into a deluxe suite at the local Four Seasons hotel by posing as Wally Shawn's son (who happens to be receiving a lifetime achievement award) and generally causes a major ruckus. By the end, Owen decides to make some changes in their relationship and in his life.