Disenfranchised from America explores the ways in which Vladimir Nabokov and Thomas Pynchon manipulate the fictional strategies of a novel in order to de-familiarize our perceptions of everyday objects and people. Estranging our regular everyday perceptions allows us to more pertinently and intensely examine the critical issues of morality and identity that have become exhausted and clichéd with over-examination. Nabokov's Lolita preoccupies us with issues of morality, but the text also brings into question the nature of love and whether it is possible in our modern era, replete with self-conscious irony, to reinvent love and make it new again. In the same vein, The Crying Lot 49 by Pynchon compels us to re-register reality through a series of eye-opening guises and events that are potent with meaning but leave us estranged, full of unanswered questions and doubts. By reexamining America through an unfamiliar perspective, these novels allow us as readers to view the world anew. Through artful use of literary technique, these novels serve to interrogate our own relationships towards such clichéd concepts as love, belonging, national identity, and finding a deeper sense of place or meaning.