1. What is your impression of Strane? How do you interpret Vanessa’s attraction to him? Do you consider him an “evil” or “sick” character?

2. At the start of her second year at The Browick School, Vanessa is lonely and withdrawn. How does this make her susceptible to Strane’s advances? Do you think her seclusion contributes to the reasons Strane is drawn to her?

3. Vanessa is underage when she first has sex with Strane, but believes that she consented and wanted his attentions. Where do you see the line that separates consent and rape in this situation? If Vanessa had been 18 at the start of their relationship, would this change your perception?

4. Discuss psychological grooming and its techniques. Do you feel you have a stronger understanding of this issue after reading the novel? What specific examples of grooming would you cite in Strane’s behavior toward Vanessa?

5. Do you think that Vanessa was the first student Strane pursued in this manner? If so, why or why not?

6. Besides her seclusion, why do you think Strane singles out Vanessa? Does any of his behavior provide insights into his decision-making process?

7. Strane tells Vanessa, “It’s just my luck that when I finally find my soulmate, she’s fifteen years old.” How do you interpret Strane expressing moral conflict over Vanessa’s youth and concern for her future? Do you think he truly knows that he is doing something wrong, or is only worried about the potential consequences?

8. How do you perceive Vanessa’s relationship with Jenny? Do you think things might have played out differently if Jenny hadn’t started dating?

9. We move back and forth in time between Vanessa’s teenage years and her present. How does Vanessa change throughout the years, or not change? What does this signify about the lasting effects of her relationship with Strane?

10. What do you think is the fundamental difference between Vanessa and Taylor and the way they respond to Strane’s advances? Do you consider their respective responses to be products of shifting cultural mores, or different upbringings, or something else?

11. Do you consider Vanessa a reliable narrator? How do you think the novel would have read differently if it were told from another character’s point of view?

12. Strane says, “We’re living in a different time,” referring to the change in attitude toward power imbalances in relationships. How far do you think society has progressed from even 10 years ago? How do you think Vanessa’s story would have changed if she had been a teenager in present day?

13. How much do you think Vanessa’s mother suspected about her daughter’s relationship before the school becomes involved? How do you interpret her response after she sees evidence of Vanessa’s relationship with Strane?

14. What do you make of Strane and Vanessa’s interpretations of Vladimir Nabokov? How do their references to his work change as their relationship progresses?

15. Vanessa muses, “Looking like a Lolita and knowing exactly what I wanted...I wonder how much victimhood they’d be willing to grant a girl like me.” How does appearance and behavior factor into our interpretations of consent, victimhood and agency?

16. How has social media shaped the way we respond to news about harassment and abuse allegations? How does the cacophony of responses help or hinder all parties involved in the case, or even others who find themselves in similar situations?

17. MY DARK VANESSA is a work of fiction, but there are many parallels to the real world. How has this novel affected your understandings of victimhood, agency and consent? Do you consider Vanessa a victim --- and why or why not?