From https://www.nytimes.com/2018/06/07/books/discussion-questions-less-andrew-sean-greer.html
1. The novel’s opening line reads: “From where I sit, the story of Arthur Less is not so bad.” Arthur Less, the book’s protagonist, is introduced as nearly 50, with “washed-out” blonde hair and “watery” blue eyes. As we soon learn, he’s also a writer less successful than his peers. How do you see Arthur Less in the opening chapters? Do you see him as a hero, as a man deserving of pity, as something else?
2. When we meet the character of Freddy, Arthur Less’s soon-to-be-former-lover, he is described as “dreamy, simple, lusty, bookish, harmless, youthful.” It is Freddy’s marriage invitation that Less so studiously avoids — choosing to go on a round-the-world trip simply to avoid having to decline the invitation without a good reason. What do you make of this decision? Have you ever found yourself doing something similarly absurd?
3. Arthur Less’s trip itinerary is as a follows: New York to interview a more popular writer, Mexico City for an obscure conference, Turin for an unknown award, Berlin for a teaching gig, Morocco for someone else’s birthday, India for a writer’s retreat (possibly during the monsoon), Japan for an article. And somewhere along the way he will turn 50. Does his sojourn remind you of any others in literature?
4. The book Arthur Less is writing is about a man on a journey through a place and his past, as he looks back on a series of disappointments. Freddy complains that Less is always writing “gay Ulysses.” Do you see echoes of or references to Ulysses or the Odyssey throughout “Less”?
5. Less’s other major relationship in the book is with the famous poet Robert Brownburn. In the chapter “Mexican,” Less recalls a day of losing his ring in the grocery store, and how, in telling Robert about it, Robert saw Less’s infidelities written across his face. “That’s what it was like to live with genius,” he writes. How does Roberts success and genius impact their relationship at the time, and how does it influence him in the end?
6. So much of Less’s focus during the round-the-world trip is on his own mishaps and foibles — or his perceived mishaps and foibles. Getting into a car with what he believes is the wrong driver because the name was a letter off. Believing he can speak German well when in fact he is bungling the words. Bringing athletic bands to every country that he will only half use. Do you see these as actual mishaps and foibles or is it a problem of perception for Less? Do you identify with that feeling at all?
7. The book alternates between Less’s trip in the present to memories of his youth — mostly memories involving nostalgia or regret. And yet the narrator tells us that Less also understands the pleasures of age: “comfort and ease, beauty and taste, old friends and old stories….” How does Less’s grappling with age play a role in the book? Is it something you can relate to?
8. In a scene at a party in Paris, Less is told that in fact he is not a bad writer, as he had come to believe, but a bad “gay writer,” in that he is not telling the narratives the gay writing community wants him to. What do you make of this critique?
9. In several countries, simply being around Less seems to make other characters sick. Why?
10. Arthur Less is self-deprecating throughout the book to a fault; in one of many descriptions he calls himself insignificant compared to other writers he knows, “as superfluous as the extra a in quaalude.” (Earlier, though, he asks if there is “any more perfect spelling” than the word quaalude “with that lazy superfluous vowel.”) Did you find these negative descriptors by Less funny or frustrating or silly or all of these? How does Greer complicate these descriptions by having some of them echo back?
11. A number of people try to tell Less about what happened at Freddy’s wedding. And while the wedding dominates his thoughts, he doesn’t listen to them. What is keeping him from hearing the story? What do you think (or hope) happened?
12. In the book, “Less” is always referred to by his last name, while Javier only by his first, and Robert Brownburn by both. Why do you think Greer chose to refer to the characters in these different ways?
13. What lines in the book made you laugh out loud?
14. Toward the end of the book, Less reunites with his supposed enemy and Freddy’s father, Carlos. When they meet, Carlos tells him that he believes that people’s lives are half-comedy and half-tragedy and that those just appear at different times. What do you make of this theory?
15. Were you surprised (or glad) to find out who the narrator was? Do any elements of the book change for you when you revisit them with Freddy as the narrator in mind?
16. The penultimate lines of “Less” (from Freddy’s voice) read: “After choosing the path people wanted, the man who would do, the easy way out of things … after holding it all in my hands and refusing it, what do I want from life?” What do you want from life? Have you similarly strayed from the path you thought you should be on?
17. After learning he won the Pulitzer Prize, Andrew Sean Greer wrote on Twitter that “Less” is a book that’s most of all “about joy.” “A writer friend once said the hardest thing to write about is joy,” he wrote. “I took it as a challenge.” Do you think he met the challenge?
From https://www.litlovers.com/reading-guides/fiction/11069-less-greer?start=3
1. Have you ever had days, weeks, years, like what Arthur Less is feeling — times when nothing, absolutely nothing, seems to be going your way? What's your solution?
2. Everyone points to the books laugh-out-loud humor. What do you find particularly funny — dialogue, Arthur's haplessness and pratfalls, random observations, the entire tone of the book?
3. How would you describe Arthur? Are you sympathetic to him, or is he primarily a self-pitying guy in midlife crisis? Does he exhibit any humanity or is he too self-indulgent to connect with others? Or do you find yourself falling and rooting for him? Does your attitude toward him change during the course of the novel?
4. Talk about the writing seminar Arthur gives in Berlin — his inventiveness in attempting to get students to fall in love with literature.
5. What do you think of the consolation his former lover/mentor offers him during the phone call from Japan? Is turning 50 all that bad (for those who've been there, done that)?
6. So at the end of his peregrinations, what has Arthur Less come to understand about his life and life in general?
7. Finally, were you surprised by the big reveal at the end?