This chapter offers an analysis of Private Romeo, director Alan Brown’s 2012 film production of the play. Set in a boys’ military high school, Private Romeo appropriates Romeo and Juliet to tell the story of two young men falling in love with one another. But, where Romeo and Juliet is a tale of tragedy, Private Romeo is very much a tale of male same-sex love’s triumph. Indeed, the happy ending of Private Romeo can be considered the film’s queerest aspect of all. Hence, as far as queer is understood in its most ‘simplistic’ sense as a challenge to all things heteronormative, Private Romeo shows how Romeo and Juliet can be thoroughly queered as opposed to merely incorporating ‘gay’ elements into otherwise ‘straight’ productions. At the same time, some critics might be troubled by Private Romeo’s representation of queerness because that queerness is wholly inflected by assimilationist capitulations. Its depiction of same-sex marriage as an ideal, inevitable outcome can be interpreted as an imposition of the kind of conformity that merely apes heteronormative conventions. Hence the need to both queer and unqueer Private Romeo.