Olga Dies Dreaming

Content Warning: This section of the guide contains discussion of antigay bias

Gather initial thoughts and broad opinions about the book.

1. The title Olga Dies Dreaming references Pedro Pietri’s poem “Puerto Rican Obituary,” where Olga “died dreaming about real jewelry” (Line 133). What was your initial reaction to this multilayered title? How did its meaning evolve for you throughout the novel? How did your understanding of the title change once you learned about the poem’s significance?

2. In what ways did Gonzalez’s combination of intimate family drama and broader political themes about Puerto Rico affect your reading experience? How does this approach compare to other novels that blend family stories with political content, such as Junot Díaz’s The Brief Wondrous Life of Oscar Wao?

3. What elements of the characters’ cultural and identity navigation between different worlds—professional and personal, Puerto Rican and American, past and present—resonated most strongly with you?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. When have you made choices in your life specifically to defy someone else’s expectations, similar to how Olga becomes a wedding planner partly as rebellion against her revolutionary mother?

2. Both Olga and Prieto struggle with secrets and maintaining successful public images while hiding vulnerabilities. How do you navigate the tension between public perception and private struggles in your own life?

3. Matteo allows Olga into his home despite his hoarding, taking a huge emotional risk in revealing his vulnerability. Think about a time when you allowed someone to see a part of yourself you usually keep hidden. What did you learn from that experience? How did it change your relationship?

4. How does Prieto’s fear of being outed as gay, which makes him vulnerable to blackmail, reflect broader societal pressures that force people to conceal important aspects of their identity?

5. The novel portrays a family culture of avoiding difficult conversations, which changes when they finally heal by openly discussing Blanca’s letters. What role has direct communication played in resolving conflicts or facilitating healing in your own relationships?

6. After Hurricane Maria, what strikes you about Olga’s decision to sacrifice her career by speaking out about Puerto Rico on national television?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The novel explores how the US government’s response to Hurricanes Irma and Maria revealed deeply entrenched colonial attitudes toward Puerto Rico. How does Gonzalez’s portrayal challenge or confirm your understanding of Puerto Rico’s relationship with the United States?

2. Olga’s explosive speech on national television about Puerto Rico’s treatment following the hurricanes becomes a pivotal moment in the novel. What responsibility do individuals with public platforms have to speak about societal injustices? What are the costs of such activism? How might this relate to contemporary discussions about celebrity activism?

3. Throughout the novel, real estate development symbolizes both exploitation and potential community preservation, similar to themes in Sandra Cisneros’s The House on Mango Street. What does Gonzalez suggest about who benefits from and who suffers from disaster capitalism?

Dive into the book’s structure, characters, themes, and symbolism.

1. Blanca’s letters interrupt the narrative throughout the novel, offering her perspective while revealing her manipulative nature. How does this structural choice affect your understanding of both Blanca and her children’s struggles? What do these epistolary intrusions accomplish that wouldn’t be possible through other narrative techniques?

2. How does Gonzalez use the recurring motif of real estate development to explore themes of colonialism, belonging, and resistance?

3. Names and naming carry significant weight in the novel. Olga is named after revolutionary Olga Garriga but fears becoming like the materialistic Olga from “Puerto Rican Obituary.” What role does this dual namesake play in Olga’s identity struggle? How does this connect to the larger theme of expectation versus reality?

4. What effect does the novel’s flash-forward to 2025, showing Puerto Rico in revolution with Blanca’s face on flags, create for you as a reader?

5. In what ways are Hurricanes Irma and Maria both literal plot catalysts and metaphorical representations of change in Olga and Prieto’s lives?

6. What do Olga’s and Prieto’s different approaches to dealing with Blanca’s expectations reveal about gendered dynamics in their family?

Encourage imaginative and creative connections to the book.

1. Write an additional letter from Blanca to either Olga or Prieto that would appear in the novel after they have both rejected her influence. 

2. The novel ends with Olga choosing not to report her mother to the FBI, dropping her phone in a gutter and going home instead. Write an alternative ending where Olga makes a different choice. How would this change the novel’s ultimate message about family, revolution, and personal freedom? What might the consequences be for both characters?

3. Which character from the novel would you most want to have a conversation with, and what would you ask them?

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