Flighty Emily "Jacks" Jackson (Brittany Murphy) works for the British edition of Vogue magazine. Rather than pursue a relationship, Jacks regularly hooks up with her devoted ex-boyfriend, James Wildstone (Elliot Cowan), and lives with Peter Simon (Matthew Rhys), a gay screenwriter. When Jacks meets Argentinian photographer's assistant Paolo Sarmiento (Santiago Cabrera), she assumes he is gay and tries to bring him and Peter together, unaware that Paolo is straight and in love with her.