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This essay aims to interrogate Lolita, based on Lacan’s desire theory, especially with his analysis on Shakespeare’s Hamlet. Lolita should not be simply considered as a love object. She transforms from the object of desire to a love object, and becomes the cause of desire in the end. In the process Humbert is born as the subject of desire. In the first stage Humbert is under the control of ‘the Other’, since Lolita conceals her lack. As Hamlet is not free from his mother(the Other), Gertrude’s domination, Humbert is also trapped in Lolita’s domination. He must moves on to the stage of ‘separation from the Other’ in order to be the subject of desire. Humbert separates himself from Lolita through the ‘estrangement’ stage, finally realizing the lack of the Other. Throughout this process, Lolita transfigures from the object of desire; the Other, into a love object. As Lacan pointed out in his analysis on Hamlet, one needs to experience a ‘loss’ and passes an appropriate mourning stage to be reborn as the subject of desire in symbolic dimension. The mourning process is an essential stage to resurrect the order of symbolic dimension. Thus, Hamlet is reborn as the subject of desire while mourning Ophelia’s death. Similarly, Humbert is born again as the subject of desire, after losing Lolita and mourning it. At that moment, he finally steps into ‘his own hour’, being free from Lolita’s control. Meanwhile, Lolita who became a love object, returns to the position of ‘the other’ as an unattainable being. Humbert succeeds in becoming the subject of desire. In this sense it could be said that Lolita illustrates Humbert’s journey of finding his own desire.