Gather initial thoughts and broad opinions about the book.

1. Discuss your overall impressions of When He Was Wicked. Which scene or image has stayed with you most strongly after finishing the book, and why?

2. Discuss When He Was Wicked in the context of the larger Bridgerton series. How did this title compare to previous titles, like The Duke and I or To Sir Phillip, With Love? What differences did you notice between Francesca Bridgerton’s love affair and her sisters’?

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

1. Francesca gradually finds love again after losing her first husband. Have you ever experienced a similarly surprising romance in the wake of a major loss? How did your experience resemble Francesca’s?

2. Francesca and Michael Stirling’s romance implies that a person can love two people fully without diminishing either love. How does their relationship story resonate with your own romantic history? Do you believe in the version of love that Quinn represents? Why or why not?

3. Michael spends six years hiding his love for Francesca, concealing his true feelings behind a public persona. When have you, like Michael, performed a public role that concealed what you actually felt, wanted, or understood yourself to be? How did you escape from this façade, and what was the result?

4. Michael finds a confidante in Colin, and Francesca leans on her mother, Violet Bridgerton, throughout the novel. Who do you go to when you need advice, counsel, or perspective?

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

1. The novel explores how social expectations placed on women limited their freedom. How does Quinn represent this dynamic, and does she affirm or challenge gender stereotypes? Consider how Francesca regards sex, marriage, and fertility compared to secondary and minor characters.

2. Discuss Quinn’s representations of widowhood throughout the novel. What does Francesca’s framing of remarriage as a means to motherhood suggest about the choices available to a Regency widow? How does Francesca weigh her social expectations as a widow against her private desires as a newly single woman who still wants a child?

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

1. Discuss Quinn’s use of letter epigraphs at the start of the chapters. What is the role of these epigraphs, and how do they set the tone for the scenes that follow?

2. Explore the novel’s point of view. What narrative, atmospheric, formal, and thematic effects does the third-person narration have? How would the novel differ if it were written from Michael’s and Francesca’s alternating first-person points of view?

3. How does the pacing of the Scottish chapters, where weeks pass while Francesca delays her answer to Michael’s proposal, differ from the pacing of the London season? Consider how shifts in geography and setting influence the characters in times of crisis, contemplation, or connection.

4. Explore how the novel represents Francesca’s shift from grief over John to desire for Michael. How do her grief and desire inform one another?

Encourage imaginative and creative connections to the book.

1. Imagine that Michael stays in London instead of fleeing to India. How do you imagine this decision would change the trajectory of his and Francesca’s relationship during those four years?

2. While Michael is away in India, Francesca doesn’t respond to his letters. Imagine that she did write back. What would she have wanted to convey to him, and why?

3. Imagine the first scene of the novel from John’s point of view. What details might his perspective reveal that Michael’s perspective leaves out? Does he fear his own death? Is he aware of Michael’s love for Francesca?