Ask Not: The Kennedys and the Women They Destroyed

Content Warning: This section of the guide contains discussion of addiction and death by suicide.

Gather initial thoughts and broad opinions about the book.

1. Callahan’s title Ask Not subverts John F. Kennedy’s famous inaugural address. How did this framing affect your reading of the book, and what expectations did it set for the stories that followed? What do you make of the book’s critical reception?

2. The book examines the stories of 13 different women across multiple generations of the Kennedy family. Which woman’s story affected you most deeply, and why do you think it resonated with you?

3. Callahan’s examination of powerful family dynamics in Ask Not is similar to Tara Westover’s memoir Educated in that both works explore how families silence individual members. How do you feel these works differ in their approach to the subject matter, and which approach did you find more compelling?

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

1. Throughout the book, Callahan shows how media narratives shaped public perception of the Kennedy women. Can you recall a time when media coverage of a public figure differed dramatically from what you later learned was true?