This reading group guide for Stay Up with Hugo Best includes an introduction, discussion questions, and ideas for enhancing your book club. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Topics & Questions for Discussion

1. June doesn’t give her roommate, Audrey, a serious answer as to why she accepts Hugo’s spontaneous weekend invitation (for “fun” and because there’s a pool at the house), but her thoughts in the moment about Hugo’s smile give us a clue. Why do you think June goes to Connecticut? If you were in June’s shoes, would you have accepted Hugo’s invitation?

2. Over the course of the weekend, June tells a number of lies: how she and her boyfriend met, what her major was in college, that she doesn’t care if people find her funny, etc. In some cases, we know from her inner thoughts that these lies are intended to subvert the preconceived notions that June, in her cynical way, suspects that other people have about her. In other cases, June is lying to herself as much as to others. Identify an instance where June isn’t being totally honest with herself. Why do you think she is avoiding this truth in particular?

3. On Saturday Hugo cracks a joke to June after overhearing a tense phone conversation she has with her boyfriend in the car. Relieved, June thinks, “Banter I could do. It was [Hugo’s] sympathy I didn’t think I could face, the thought that I had come here and made him feel bad for me” (page 64). Why is June so loathe to accept Hugo’s sympathy? What does this scene reveal to us about the role banter, and more generally humor and comedy, play in her life?

4. Spencer and June are closer in age than June and Hugo. Compare their respective roles within their own families, based on June’s memories of her parents’ visit to New York (p. 124) and Spencer’s interactions with Hugo over the course of the weekend. Which family would you rather be a member of?

5. “I wanted [Hugo’s] fame and hated that I wanted it,” admits June (page 201). How do June, Hugo, Spencer, and Julian see fame differently? Is fame more than a fickle friend for anyone in the novel?

6. During his interview with Casey Caruso, Hugo emphasizes the importance of supporting female comics despite dismissing June’s points about inclusivity the night before. June wonders if he has stolen her ideas simply to make himself look good or if he has genuinely learned something from her. Which do you think is true?

7. Discuss your reactions to the revelation about the fan who stabbed Hugo. In what ways, if any, did this change your perception of him? Why do you think Hugo keeps the details a secret from Spencer?

8. There is a lot of comedy in Stay Up with Hugo Best. For June’s father, comedy is “for making people laugh”; for June, comedy is meant to “challenge the culture” (page 128). Which did this novel as a whole do more of for you?

9. From Kitty Rosenthal to the events aboard Duck Soup, discuss how Hugo and June’s relationship comments on the #MeToo movement and the questions raised about power dynamics and sexual assault. Did Hugo have “funny business” on his mind the whole weekend?

10. June is twenty-nine years old and well past her teenage years. Nevertheless, Stay Up with Hugo Best can be thought of as a coming-of-age story. How has June changed in the three days she spends in Connecticut?

11. We learn Hugo’s fate at the end of the novel. Where do you imagine June will be in five years? What will she be doing with her life?

Enhance Your Book Club

1. With your book club, check out recordings of some of the comics June and Hugo idolize, including Don Rickles, George Carlin, Bob Hope, Richard Pryor, Lenny Bruce, and Andy Kaufman, and discuss your reactions to their various styles of comedy.

2. Read Labor Day by Joyce Maynard or Independence Day by Richard Ford, two other novels set over holiday weekends. Compare the techniques used by the authors to tell a complete story over a short timeline.