Since its publication in 1955, Vladimir Nabokov’s contentious novel Lolita has stirred heated controversies that originated from Nabokov’s treatment of a thorny subject matter. What makes his achievement so stupendous is that he penned a book about a forbidden desire and succeeded in persuading his reader to feel for the deviant. The present study intends to fathom Nabokov’s success in his art of deception drawing on Søren Kierkegaard’s existentialist ideologies of aestheticism and despair in order to offer a new insight regarding the elements used in Humbert’s narration and character which bestow upon him the distinctive personality of the aesthete. Referring to Kierkegaard’s spheres of existence introduced in his “Either/Or,” it is suggested that Humbert, similar to Kierkegaard’s Johannes, aesthetically alienates himself from commitment and consequence while keeping an eye open for the interesting and relishing sensual immediacy. It is this shrewd aestheticizing of Humbert’s character that grants him his unique status that has elicited both attraction and aversion.