Bring on the tough stuff - there’s not just one right answer.
How does the Foreword influence our reading of Humbert's "memoir"? How are we meant to regard the Foreword's idea that the memoir is a "case study" with moral lessons? How do Ray's Foreword and Nabokov's Afterword speak to each other?
What is the effect of knowing from the beginning that the three main characters involved in the story are already dead?
How does Humbert draw attention to the act of writing? Why does he do this?
Can Humbert ever be said to "love" Lolita? Does he ever consider her a being outside of his own imagination? Is the reader ever able to see Lolita in ways that Humbert cannot?
Is Humbert likable? Why or why not?
Early on, we learn that Humbert is insane enough to have committed himself to several mental institutions, where he enjoyed misleading his psychiatrists. Is Humbert's madness an excuse or a reason for his sexual deviance? Can we trust a story told by an insane narrator?
From the start, Humbert sees Lolita merely as an incarnation of Annabel, even making love to her on different beaches as he tries to symbolically consummate his earlier passion. Do we believe this effort is genuine or is it just another example of his mockery of psychoanalysis?
Does Humbert ever succeed in escaping the past? Why is Lolita able to get past her very troubled childhood, to the extent that she can even move past the abuse inflicted on her by both Humbert and Quilty, and live a somewhat normal married life?
Is Lolita a moral story despite Nabokov's insistence in the Afterword that it is not?
If we believe Humbert, Lolita initiates their first sexual encounter. Yet later Humbert admits that "Lolita sobs in the night—every night, every night—the moment I feigned sleep" (2.3.18). Does what begins as a game for Lolita become a brutal and inescapable reality? Or is Humbert been lying to us from the first?
Does Humbert ever genuinely repent for his crimes, or is even his remorse a sham?
Humbert's first nymphet love is Annabel Leigh, inspired by Edgar Allan Poe's Annabel Lee (of the poem "Annabel Lee"). Aside from Annabel, can you find any other connections between Lolita and Poe's works?