Orange is the New Black: My Year in a Women’s Prison

Content Warning: This section of the guide contains discussion of sexual harassment, substance use, and addiction.

Gather initial thoughts and broad opinions about the book.

1. Kerman’s memoir offers a markedly different perspective from fictional prison narratives like Stephen King’s novella, Rita Hayworth and Shawshank Redemption. What aspects of her real-life experience surprised you most about women’s federal prison? How did the day-to-day realities challenge any preconceptions you might have had?

2. Which transformation in Kerman’s character felt most authentic to you as she moved from considering herself stoic and independent to valuing interdependence and community?

3. How effectively does Kerman balance her personal story with broader critiques of the prison system?

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

1. Kerman describes feeling like the black sheep of her educated family before prison, drawn to “bohemian counterculture” rather than traditional career paths. Have you ever felt pulled between family expectations and your own desire for adventure or nonconformity?

2. In Danbury’s “tribal system,” newcomers receive an immediate welcome from their respective groups. Have you ever experienced anything like this? How did it make you feel?

3. Kerman’s steady stream of books, letters, and visits sets her apart from inmates who receive nothing during mail calls. In what ways has your support network shaped your ability to weather difficult periods? 

4. Pop’s role as a “prison mama” to younger incarcerated women reflects how traditional family structures adapt in different setting. What examples have you seen of people creating chosen family relationships in challenging circumstances?

5. What resonates with you about Kerman’s realization that she needs other people more than she previously understood? Have you ever had a similar realization?

6. Considering Kerman’s privileged background compared to other inmates, how do you think your resources and education would affect your ability to cope in a similar setting?

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

1. What does Kerman’s experience at the Danbury job fair reveal about the disconnect between prison officials' assumptions and incarcerate people’s actual needs for successful reentry? How might society better prepare incarcerated individuals for life after release?

2. How does the sexual harassment Kerman experiences from guards like DeSimon reflect broader power imbalances in institutional settings? What systemic changes might address these vulnerabilities while maintaining necessary security?

3. Most women at Danbury received drug convictions yet few access treatment programs. How does this reflect broader societal approaches to addiction as a criminal versus medical issue? What implications does this have for effective public policy?

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

1. How does Kerman’s relationship with books both connect her to and separate her from fellow inmates? What do her reading habits reveal about privilege and identity within the prison community?

2. What role does food play in creating community and maintaining cultural identity within Danbury’s constraints?

3. Kerman structures her memoir chronologically without flashbacks, moving steadily from crime to sentencing to incarceration. How does this linear approach serve her goals as both a personal narrative and a prison system critique? What might have been lost or gained with a different structure?

4. The stark contrast between Danbury Federal Prison Camp and Chicago MCC illuminates different approaches to incarceration. What does Kerman’s experience in both facilities suggest about the purposes and effectiveness of different correctional institutions?

5. How do the mother-daughter relationships that form in prison reflect broader themes of family, care, and survival in institutional settings?

6. Kerman’s transfer to Chicago near the end disrupts the community she’s built at Danbury and forces her to testify against someone she’s never met. How does this experience reinforce the memoir’s themes of institutional power and individual agency?

Encourage imaginative and creative connections to the book.

1. Imagine you’re designing a rehabilitation program for a women’s federal prison camp based on Kerman’s observations about what inmates need versus what they receive. Describe three core components you would prioritize and why.

2. Kerman’s story ends with her running toward Larry outside the Chicago MCC. Describe what you think her first week of freedom might look like, considering how her prison experiences would affect her reintegration into outside life.

3. Write a short paragraph from Pop’s perspective about the months following Kerman’s release as she continues serving her long sentence at Danbury.

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