Spoiler alert: If you haven’t read the book yet, you may not want to read on.
1. Mr. Vernon gives his students “Official Member of the Human Race” cards that state: “So make daring choices, work hard, enjoy the ride, and remember—you become exactly whomever you choose to be.” Do you believe this is true? Is it a good message to give young people? Why or why not?
2. When we first meet Portia Kane she is drunk, planning to kill her husband, and using a lot of profanity. What was your initial impression of Portia? Did your opinion of her change? How so?
3. Coincidence certainly plays a large role in the story. Sister Maeve believes her being seated next to Portia on the flight from Tampa Bay to Philadelphia is divine intervention. Regardless of whether you are religious or not, have you ever had a chance meeting that seemed destined or made you wonder if there was a certain rhythm to the universe? How has coincidence shaped your life?
4. Portia first falls for Chuck when she sees him performing a Bon Jovi song with his nephew, Tommy. As luck would have it, Portia and Chuck share a love of eighties hair metal. What music did you love when you were a teenager? Do your favorite songs from high school still define you? Are you more likely to befriend someone who loves a certain type of music?
5. How would you characterize a normal relationship between a person and a dog? Juxtapose that with Mr. Vernon’s relationship with his dog, Albert Camus.
6. At one point, Portia tells Mr. Vernon that he is now using literature to put bad into the world. Compare the Mr. Vernon who once taught high school English to the Mr. Vernon who lives alone in Vermont. Account for the differences. Does aging decrease our ability to believe in the greater good?
7. Was Portia’s high school relationship with Mr. Vernon healthy? Is her adult relationship with him healthy?
8. Discuss Sister Maeve’s relationship with Mother Catherine Ebling (aka The Crab). Do you believe that some people are connected to higher powers?
9. Do you feel more sympathy for Mr. Vernon or his mother? Why?
10. When discussing Danielle, Portia tells Chuck that it’s very hard for uneducated single mothers to support themselves. What factors lead to Danielle’s overdose? Consider the fact that one Bass sibling is able to beat drug addiction and one is not. Does Danielle’s gender play a role? Does society?
11. When Portia begins writing fiction, she misses family dinners and spends less time with Tommy and Chuck. When she finds an agent and a publisher, she out-earns her significant other. Discuss Chuck’s reaction to this new reality. What does it say about his character?
12. Portia’s ex-husband, Ken, leaves his lucrative pornography business to do Catholic missionary work with his new wife, who is half his age. Portia struggles to wrap her mind around this. Do you know someone who has radically changed his or her life? How did it make you feel?
13. Are Portia and Chuck a good match? Explain your answer.
14. “Love may fail, but courtesy will prevail.” Discuss that Kurt Vonnegut quote. What does it mean? Do you believe it’s true? Why did the author choose to title the book ‘Love May Fail’?
15. Did a teacher change your life for the better? How so? Have you ever told him/her what he/she did for you? If not, is that teacher still alive? If so, why not write him or her a thank you letter now? (If you’ve never taught, you have no idea how much it would mean to your former teacher. Seriously. Write that letter!)