53 pages • 1-hour read
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Content Warning: This section of the guide includes references to sexual content.
Gather initial thoughts and broad opinions about the book.
1. Discuss your overall impressions of I’ll Have What She’s Having. What were the most and least affecting aspects of the memoir, and why?
2. How did your experience reading I’ll Have What She’s Having compare to your experience reading Chelsea Handler’s other texts? What crossovers and/or divergences do you notice between this title and titles like Life Will Be the Death of Me, Are You There, Vodka? It’s Me, Chelsea, and My Horizontal Life?
3. What other celebrity memoirs or self-help titles is I’ll Have What She’s Having in conversation with? Discuss parallels between Handler’s title and titles like Julia Fox’s Down the Drain and Tina Fey’s Bossypants.
Encourage readers to connect the book’s themes and characters with their personal experiences.
1. Reflect on the essays “Poopsie, Whoopsie, and Oopsie” and “De Facto Parenting.” What surprised you about Handler’s relationship with Poopsie, Whoopsie, and Oopsie? How did it alter your impressions of Handler?
2. Handler openly discusses her therapy journey throughout the memoir. How does her quest for self-understanding and self-healing relate to your own internal journey?
3. Handler incorporates allusions to and descriptions of her intimate relationships throughout the text. How do her romantic and sexual experiences compare and contrast with your own? What were the most and least resonant aspects of Handler’s relational anecdotes?
4. Handler puts a premium on family relationships. How do you see her family life relating to her sense of self? How do you understand yourself in the context of your biological or chosen family?
5. Handler’s conversation with Jane Fonda in Chapter 7 is a turning point in her life. Have you ever had an awakening moment like this one? Discuss how it changed you and why.
Examine the book’s relevance to societal issues, historical events, or cultural themes.
1. I’ll Have What She’s Having is as much a letter to Handler as it is to her reader. How does Handler apply her own life lessons to her audience of women? What role does Handler’s voice play in the contemporary women’s right movement?
2. The memoir revolves around Handler’s therapy and personal growth journeys. Explore how Handler’s account relates to contemporary mental health awareness and messages of self-care. What is Handler advocating for via her own search for balance? Is her writing socioculturally sensitive; why or why not?
Dive into the book’s structure, characters, themes, and symbolism.
1. The essays and vignettes in I’ll Have What She’s Having largely follow a linear timeline. Analyze the significance of Handler’s overarching structure. How does it relate to Handler’s explorations of growth and change?
2. Handler uses multiple points of view and tonal registers throughout the memoir. Explore the significance of Handler’s authorial stance and tone to her overarching message. What do her formal choices accomplish and how do these effects develop her themes?
3. Handler uses personal anecdotes throughout the memoir. Explore the formal, aesthetic, and rhetorical effects of these personal accounts. How would the memoir’s mood change if Handler didn’t incorporate episodes from her own life?
4. References to and descriptions of Handler’s Mallorca and Whistler houses appear throughout the memoir. Discuss the significance of these settings to Handler’s personal and relational journeys.
Encourage imaginative and creative connections to the book.
1. In Chapter 1, Handler describes the woman she wants to be and in Chapter 49 she describes the woman she has become. Using Handler’s chapters as a model, write a description of the person you hoped to be when you were young; and write a letter to yourself about the person you have become since. What surprises do your exercises unearth for you personally? How does using Handler’s form facilitate new reflections for you?
2. Create a playlist that evokes the moods of Handler’s personal growth over the course of the memoir. Consider the experiences and relationships that encourage Handler to change. Consider also the joys and successes she experiences along the way. Share your playlists and discuss your reasoning behind each song.



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