There are debates whether Pedophilia, a universal psycho-social problem, is a psychiatric disorder or a perverse sexual orientation. Though a few number of pedophilia supporting groups argue that having sexual interests in children is merely a sexual orientation or fantasy; but this paper explores further in analyzing different psychological insights of pedophiles, especially in the contexts of Vladimir Nobokov’s novel Lolita (1955) and its film adaptation of 1962. This paper gives a critical analysis of the views and practices of pedophilia in the contemporary world. In addition to that, this paper explores the binary opposite characters of Humbert and Clare Quilty to determine whether pedophilia is their sexual orientation or they are perverts who are only sexually attracted to young girls. Apart from analyzing this perverse sexual practice, this paper also discusses the established notions of pedophilia, re/de-constructs them and gives an elaborate discussion on this taboo topic from theoretical points of view. In doing so, this paper employs critical commentaries based on a number of established theories like Michel Foucault’s theories on Sexuality, Sigmund Freud’s psychoanalysis and Laura Mulvey’s envision of scopophilia.