This paper is an attempt to explore how Lacanian concepts of desire, unconscious, as well as alienation are reflected in the major characters of Vladimir Vladimirovich Nabokov’s Lolita. Before unleashing the new, inexplicable yet highly fascinating aspects of psychoanalysis by the advent of French poststructuralist and psychoanalyst Jacques Lacan, Freudian psychoanalysis used to play the pivotal and, accordingly, unique role in the realm of literary criticism which suffered from some drawbacks and left many questions unanswered in the psychoanalytic sphere. However, under the auspices of Lacan, almost all of these eerie ambiguities have already been resolved. It would be a gross underestimate that expressing Lacanian concepts in simple words is feasible, since Lacan stipulates that “unconscious is complex, so that the language used to express it, inevitably, should be complicated” (Écrits, 24). The present paper aims to elucidate the ulterior reasons underling the interactions of the three main characters in Nabokov’s Lolita through Lacanian model for the development of psyche, namely: Imaginary Order, Symbolic Order, and the Real.