A handsome high school student obsessed with his good looks (Samberg, portraying Gene Hackman as the protagonist) is cursed by a witch (Nasim Pedrad), who transforms him into the same nerd that Samberg played in the previous Digital Short The Roommate. Having been informed by the witch that he has one year to find someone to love him "or stay like this forever", he falls in love with a girl (played by episode host Miley Cyrus) who seemingly attempts to find his inner beauty, albeit unsuccessfully.

The second consecutive Digital Short to parody a then-recent Hollywood release, it appears to be the origin story for The Roommate character, implying that he was unable to break the witch's curse.