The plot of the movie revolves around two newlyweds Carl and Molly Peterson ( played by Matt Dillon and Kate Hudson ) . After Carl 's best man and friend Randolph Dupree ( usually just called `` Dupree '' ) ( Owen Wilson ) , loses his job and apartment , the couple allow him to move in but Dupree inevitably overstays his welcome . Carl asks Dupree to go to career day at Molly 's work as he got tied up at his work and that night Dupree cooks a large dinner for Molly , though Carl is late again , so Molly and Dupree start without him .