Apuleius is often considered to be a Latin sophist, a master of narratological and hermeneutic games, with no particular philosophical agenda. But complexity and playfulness are not necessarily synonymous with intellectual or moral emptiness. Indeed, Apuleius’ self-proclaimed Platonism links him to a figure whose very choice of medium, the dialogue, always plays philosophical games with the reader. This dissertation shows that Apuleius engages with Plato on a deeper level than has previously been thought, framing both his own texts and those of Plato in terms of a high-stakes choice to the reader in the spirit of the ‘choice of Heracles’. I focus on Apuleius’ use of the mirror trope – a trope he inherits from Plato but refracts through the Roman literary tradition. I argue that when Lucius looks into mirrors in the Metamorphoses, such as the mirroring water of Byrrhena’s atrium or the catoptric hair of the maid-servant Photis, Apuleius invites the reader into a complex game of identification and criticism. Lucius’ specular contemplation, though he attempts to fashion it after idealized Platonic mirroring encounters, begins to appear more like the delusional mirror-gazing of Ovid’s Narcissus or Seneca’s Hostius Quadra upon further analysis. Readers, who have been tricked into participating in a shared voyeurism with Lucius, are compelled to see themselves at the same time as they see Lucius in the mirror. At that moment, the reader is put into a kind of Platonic bind, whereby he or she is forced to choose whether or not to continue following Lucius into voyeuristic delusion.