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How to Look Good Naked positions Gok Wan as a highly empathetic media figure in popular media. Having a first-hand experience in dealing with body-image discontent and low body-confidence, Wan's highly empathetic approach towards his subjects' body-image concerns derives from his own earlier personal experience in dealing with weight struggles and eating disorders. This paper explores how the processes of emotional development depicted in How To Look Good Naked bring to the surface Gok Wan's own unresolved experience with his body-related struggles. The crucial role of the show's emphasis on the ‘mirror sequence’ in enabling this reading is examined in detail. This article makes use of the work of Donald Woods Winnicott, and also Melanie Klein's object relations theory, applying their ideas to selected episodes of How to Look Good Naked in order to raise the question of what is at stake emotionally for the makeover expert in his work on the programme. The article also discusses the themes that recur in media narratives created by Gok Wan around his persona, exploring how his personal experience is echoed in the television strategies and formats popularised in the show.