This reading group guide for Lily and the Octopus includes discussion questions, ideas for enhancing your book club, and a Q&A with author Steven Rowley. 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. Ted agonizes over the fact that Lily’s octopus has gone unnoticed by both of them for so long. Discuss how he internalizes his grief, transforming it into guilt. How would you react in his shoes?

2. The book is divided into eight sections, each with an octopus-related theme. What other octopus imagery and symbolism did you find in the book?

3. Ted hates “living in the not knowing” (p. 31). How does this aversion to uncertainty affect his personal relationships? Do you think this attitude changes over the course of the novel?

4. There is a level of trust shared between Ted and Lily that does not seem to extend to the humans in his life. Discuss how trust requires a kind of courage that humans find difficult to muster. Is it possible to replicate the unconditional love of a dog? Why or why not?

5. Ted notes that Lily has been the closest witness to his life. Discuss why this is clarifying for him. How can new perspectives become powerful?

6. Throughout the novel, we learn that omens can be just as bad as they are good. What happens when Ted goes looking for more omens? Where do they lead him?

7. What role does forgiveness play in this novel? Who does Ted ultimately make peace with, and at what point?

8. Lily admits that she has not held onto a single bad memory. In fact, she does not have many memories at all. Still, she adores Ted’s stories. Discuss how memories can become their own forms of storytelling. What does Ted learn from distilling their shared history?

9. The vet has warned Ted that as she gets older, Lily may start to encounter Enclosed World Syndrome. How is this syndrome mirrored in Ted’s own life? Do you recognize the phenomenon?

10. Ted catches a glimpse of himself in the glass door by the pool and recognizes the octopus. Discuss the meaning of this scene. Why do you think this conflation of identity occurs in his mind’s eye?

11. The tattoo artist, Kal, claims to enjoy the permanence of his work. Ted is skeptical that permanence even exists. Did you see anything in the novel that you felt to be permanent? If so, what was it?

12. One idea that Ted is partial to is karma. Karma implies a sense of causality and order to the universe. Do you think that his opinion evolves as Lily gets sicker?

13. Discuss the scene in which Ted finally acknowledges that the octopus is, in fact, a tumor. What has changed? Did he kill the octopus? What is the significance of this semantic twist?

14. Lily loves her red ball. Ted even goes so far as to suggest that hers is not a life without it. Discuss the symbolism of the ball, especially in Ted’s dream when he loses Lily in a storm of them.

15. What does Ted see in Byron? Do you see a happy future for the two of them?
 

Enhance Your Book Club

1. Ted takes solace in the J. M. Barrie quote “To die would be an awfully big adventure,” and the book calls upon Rudyard Kipling for its two epigraphs. Did you read Peter Pan or The Jungle Book? Discuss your memorable childhood reading experiences and whether you would go so far as to tattoo a favorite line on your body.

2. W. H. Auden’s “Funeral Blues” is a beautiful poem of all-encompassing grief. Pull up a copy and read it aloud together. Compare and contrast the lines that resonate with each of you, sharing any memories that they evoke along the way.

3. In honor of Lily and Ted’s last great adventure, take a group trip to the local aquarium or science center to consider the octopus or any of its underwater friends in their natural habitat. (Take care to remember that they are not all evil!)

4. Everyone needs a good pep talk once in a while. Treat yourselves to an episode of Friday Night Lights and soak in Coach Taylor’s inspiring words.
 

A Conversation with Steven Rowley

Lily and the Octopus came about when you began jotting down memories of your own dear dachshund. Was this writing experience cathartic for you? Did it surprise you in any way?

It was indeed cathartic. Six months after my dog died of cancer, I wrote what became the first chapter of Lily and the Octopus as a short story to help process my grief. I didn’t expect it to go anywhere; I was just doing what writers often do—putting feelings down on paper to get them out of my heart and my head. I shared the story with my boyfriend, who encouraged me to keep writing. Still, I felt the story was so deeply personal (and disconcertingly weird) that I wasn’t sure it would connect with anyone who didn’t know me or didn’t know my dog. What has been surprising (and deeply humbling) is the way the book has resonated with so many readers—dog lovers and non-dog lovers alike. I tried to write Lily’s story with unflinching emotional honesty, and the connection that people seem to feel, despite the magical realism, is a testament to the power of the truth.       

You have also worked as a screenwriter. What do you think are the main differences between the two mediums? Do you have a preference?

When I decided to write Lily and the Octopus as a novel, I removed my screenwriter’s cap and threw myself into the medium entirely, and it was incredibly freeing. Not once did I have to think about something being too expensive to build, too hard to cast, or too impossible to film. My only limits were those imposed by my own imagination. Talking dog as a main character? Sure. Octopus stuck to dog’s head? Why not! Expansive battle at sea? Yes, please. I’ve always enjoyed writing dialogue, which lends itself to screenwriting. In the course of writing this book, I became really taken with crafting prose and the pace and depth at which you can really explore what’s going on inside a character’s head. Screenwriters have to externalize the internal, show what’s going on through action and dialogue, and that can be difficult.

As a screenwriter, you’re part of a team—one of many people who bring a story to life. Novelist is a much more solitary occupation. Collaboration can be fruitful, but it is often not the writer’s vision that makes it to the screen. Likewise, a novel doesn’t make it to the shelves without a real team of people who believe in the story, but for me it has been so rewarding to create something that itself was the final work and have my vision honored.   

If Lily and the Octopus were adapted for film, who would be your ideal cast?

There are particular actors I imagine in the role of Ted, actors who have an inherent sadness to them and can convey a lot by doing very little. A certain stillness is important. Ewan McGregor and Jake Gyllenhaal are two actors who I think are wildly underappreciated. Paul Rudd, I think, has untapped dramatic range. Jude Law. I keep naming incredibly handsome actors. Hmm. The voice of the octopus as I was writing was always Eddie Izzard’s—and I mean that as the highest compliment. I am a huge fan and cannot imagine a more polished, brilliant, or formidable foe. I don’t picture a film version where Lily actually speaks, as so many of her conversations with Ted are imagined. But I can’t imagine a happier process than sitting with a casting director in a room full of dachshunds of all ages.     

The narrative puts a lot of weight on naming and nicknames. Lily has an abundance of them, while Ted is mainly relegated to “that guy.” There is also a poignant moment in which Ted and Jeffrey become only that to each other. Discuss the power of naming as it plays out in both the novel and real life.

One of my favorite moments in the book comes when Trent calls Ted Theodore, even though his full name is Edward. I think that one shorthand sums up their relationship perfectly and tells you everything you need to know about their friendship. Naming characters is hard for me, because I do indeed believe that names carry a lot of weight. Sometimes a name has the proper rhythm or length and it simply sounds right. I have three siblings whereas Ted has only one, so the three-syllable name given to Ted’s sister, Meredith, allowed me to honor them. Lily in real life stemmed from Little Weiner Dog, and Lily became its own term of endearment. I do think it feels formal and stilted when people who are very close call each other by name, particularly those in romantic relationships. Ted was the last to be named. For the longest time he was simply “The Narrator,” but people too often conflated him with me. I wanted him to have his own identity, and there is a huggable quality about the teddy bear that I hoped the reader would also feel for Ted. The last name I ripped straight from Melville. Flask was the third mate aboard the Pequod in Moby-Dick and was a man who seemed to regard the whale’s very existence as a personal affront.     

Ted considers Lily to be his best friend, but he also has a very strong human support system—Trent, Meredith, his mother. Where did you get the inspiration for these characters? Do you think that Ted appreciates them in the same way that he appreciates Lily?

I wanted Ted to be as isolated from people as possible in order to enhance and spotlight the special relationship he has with Lily; he has one parent, one sibling, one friend. They are an excellent support system in that they will always be there for him, even if at times his first instinct is to keep them at arm’s length or to push them away. And I do think he appreciates the people in his life, but not in the same way as he does Lily—simply because she is there. Dogs don’t let you keep them at a distance. They will doggedly push their way into your life, like it or not. It’s also hard to craft a separate persona to present to a dog, the way humans often present somewhat different or edited personas to the various people in their lives. Dogs generally see the whole you and love unconditionally. I think there’s a part of Ted that thinks the love he has from people is somehow conditional, and that prevents him from fully letting go.   

The book takes place in Ted’s early forties, a stereotypical time for midlife crises. Indeed, Ted muses that “this is the halftime of my life, and my team is losing.” Tell us how you would approach a “halftime” in your own life. What helps you get perspective after a fumble or two?

I thought it was important for Ted to be well-worn, a little weathered with a heartbreak or two under his belt, but too young to be pinned against the ropes or to tap out and not fight again. To me, that’s your early forties. Or maybe it’s as simple as I was in my early forties when I wrote the first draft of the book. In either case, turning forty is a bellwether moment for many people. My forties have been the first time I have fully felt like the person I was meant to be. It’s with that confidence and sense of self that I pick myself up after fumbles now. It’s so much easier to get back up and stand tall when you really know who you are. 

The ocean—both the LA coast and the open sea—figures heavily throughout the novel. It is almost a character in its own right. Do you have a personal connection to the water? And—as a Maine native and California transplant—do you prefer the Atlantic or the Pacific?

The ocean has played a huge role in my life. I grew up in Portland, Maine, and have lived most of my adult life in Los Angeles. I’ve never lived far from the ocean, and I think I would panic if I had to. The word landlocked sends shivers down my spine. I’ve contemplated my life’s big decisions—moving across the country, coming out, ending relationships—while sitting on a beach or looking over a cliff staring at the sea. That said, I think everyone who loves the ocean also has a healthy fear of the ocean, or at least a respect for its sheer size, deep mysteries, intelligent life, and awesome power. The octopus is an octopus in part because I wanted the novel’s antagonist to come from the ocean. To be both of this world and not.

For everything but swimming—for its seafood, for its rocky shoreline, for its moody vistas—I prefer the Atlantic Ocean. There’s nothing like your first love.    

You are clearly an avid Kipling fan. Who are your favorite literary beasts in (and out of) the canon? What do you think made them so memorable?

I love Kipling’s The Jungle Book, although I forget when I was introduced to his work. It may have been as a Cub Scout. I know that growing up I had a short story version of “Rikki-Tikki-Tavi.” The Kipling quotes from “The Law of the Jungle” that serve as the book’s two epigraphs were quotes that I jotted down early in the writing process and referred back to throughout. I love thinking of Ted and Lily as a pack, and there’s something comforting about laws, even violent ones, providing structure in the vast jungle that is life; laws that are defined and understood from the outset. Death is a part of life. The earlier one understands this, the more fully one can live. Opening the book with a quote from The Jungle Book helps underscore the fable elements of Lily and the Octopus. I also am a huge fan of blurring lines between prose and poetry, building a rhythm and cadence through word choice, sentence length, repetition, and other literary devices that Kipling excels at.

Other writers who have inspired me include John Steinbeck, Michael Chabon, Donna Tartt, Jonathan Franzen, Richard Russo, Joan Didion, and Francesca Lia Block, whose book Weetzie Bat (another prose poem) was handed to me at a critical moment in my life.   

Other than the uncanny physical similarities, why choose an octopus? What kind of research did you do on the species, and what is your favorite piece of trivia?

I chose an octopus because they are smart, wily, and slimy. They can learn, adapt, and even (according to numerous scientists) play. I needed a foe that would needle Ted, toy with him, study his weaknesses, and adjust, just as cancer mutates in the body. It helped the story that they are in many ways the physical opposite of dogs, especially dachshunds. A hairless invertebrate that lives in the sea is nothing like a furry dog that is all spine and lives on the land. I did an incredible amount of research on octopuses, and gave each of the book’s eight sections an octopus theme. There are so many fascinating facts about them it’s hard to pick a favorite; in writing the book it was hard to shake their having three hearts. Once I learned that piece of trivia, I knew the entire book would be driving toward that end.

While the octopus as villain fit the needs of this story, I want to be clear that they are magnificent creatures and are in no way inherently evil. I am quite in awe of them, really!  

Do you think Ted and Byron will adopt another dog? Will it be a dachshund?

I do think that Ted and Byron will adopt a dog, but I don’t think it will be a dachshund. I think Lily is irreplaceable to Ted, and just as Byron is very different from Jeffrey, a new dog will be different from Lily. No judgment here toward others who feel differently, but limiting oneself to one breed always struck me as odd. As does the idea of there being another dachshund named Lily 2. I imagine that Ted and Jeffrey would adopt a dog from an area shelter—just as I would encourage readers of Lily and the Octopus in the market for a dog to do.