1. What qualities and skills make a great teacher? In what ways might the answer change at different levels of education? Who are your memorable teachers?

 

2. How did Portia find herself in such a troubled marriage with Ken, a man so much different than her? What might have caused her to be, as she says, “addicted to horrible men”?

 

3. What complex ideas are introduced by Portia’s many references to Gloria Steinem? How do you define feminism?

 

4. How has Portia’s mother --- “honest as a mirror” but also very emotionally ill --- affected her? What were her particular childhood challenges? What kind of relationship is necessary for Portia’s health?

 

5. What is Mr. Vernon like when we first meet him in the classroom? What seems essential to how he addresses the students?

 

6. Mr. Vernon powerfully quotes Ernest Hemingway to his students, saying that the world “kills the very good and the very gentle and the very brave impartially.” What might this mean? In what ways is it true or not? Why present such an idea to high school students?

 

7. The day before his violent attack of Mr. Vernon, Edmond Atherton attempts to explain himself. Why is he so angry and disappointed? What might be true or logical in what he says?

 

8. In what ways is Mr. Vernon’s profound admiration of Albert Camus healthy or harmful for him? Which of his ideas is most compelling?

 

9. What particular qualities attract Portia to Chuck Bass?

 

10. How is it that misogynistic pop metal music from the 80s proves valuable to Portia, Chuck, and especially Tommy? How is it helpful for each?

 

11. As Portia tries to “save Mr. Vernon,” he criticizes her for “mythmaking and romanticizing the past.” What does he mean? Could this be a positive or even necessary way to think about the past? How is it related to nostalgia?

 

12. Somewhat ironically, Portia largely educates herself by reading extensively after quitting college. How necessary is it, then, to have teachers? What might she have missed without them?

 

13. A central theme in the novel is kindness. Which of the many references to it seem most poignant? Why is kindness so valuable? How does it work? Why might it be difficult for some to receive?

 

14. Religion is a powerful force for several characters in the novel, not the least of which are Sister Maeve and Mother Catherine. How is their faith helpful to other characters? Why is it also the hurtful cause of Mr. Vernon’s break with his mother?

 

15. Consider the profound coincidences of Portia meeting Sister Maeve and Chuck meeting Mother Catherine. Are these acts of God? What might be a secular explanation for such events?

 

16. While Portia and Mr. Vernon long had similar dreams to be novelists, Mr. Vernon is never able to act on this like Portia does. Why is this? What’s behind the motivation to act on one’s dream?

 

17. In a complex move, LOVE MAY FAIL takes us through the critical failure of a novel with the same name. What effects does this have on the reading? What ideas are introduced by it?

 

18. Consider the quotation from Kurt Vonnegut's JAILBIRD, from which the novel’s title is taken: “Love may fail, but courtesy will prevail.” What might this mean? How is courtesy more reliable than something as profound as love?

Love May Fail
by Matthew Quick

• Publication Date: June 21, 2016
• Genres: Fiction
• Paperback: 416 pages
• Publisher: Harper Paperbacks
• ISBN-10: 0062285572
• ISBN-13: 9780062285577