1. At the beginning of the novel, we are told about the unique phenomenon of synesthesia, which plays a major role in HESTER. In what ways does Isobel’s synesthesia serve to propel the narrative forward?

2. Early in the novel, on page 5, Isobel’s Auntie Aileen says, “To clothe a woman is to hide her failings and frailties.” Throughout the novel, Isobel helps to clothe many women, including herself. Does Isobel take the same view toward clothing as her aunt, or is her approach more nuanced?

3. Examine the various positions and choices that women in the novel are given and have to overcome. What journey did each of these women take, and who do you think ultimately overcame the most?

4. Isobel’s embroidery is an essential part of who she is and allows her to express her internal creative process in a way the world values. Do you have a creative outlet or form of creative expression that is important to you?

5. On page 190, Isobel tells Nat, “Women want to read love stories to know if a man is good, if love is true, who and what can be trusted.” Discuss the different men in Isobel’s life. In what ways is the truth of this statement revealed through HESTER?

6. Discuss the significance of Isobel’s colors. What do you think it means that she has lost them at certain points in her life and gained them back? Why do you think she is unable to see colors with certain people?

7. On page 252, Isobel asks herself whether Nat is a cruel man or a weak man. By the end of the novel, what is your opinion on Nat’s cruelty or weakness? Is it possible for someone to be both?

8. HESTER is a novel that imagines the inspiration for Hester Prynne, the heroine of THE SCARLET LETTER. If you have read THE SCARLET LETTER, does Isobel’s story resemble how you might have imagined this woman’s life?

9. Scottish myths and elements of the magical world run throughout the novel. How does Isobel’s belief in magic and the spirit world change throughout the novel? What do you believe is real or possible?

10. Consider Isobel Gowdie and her legacy, as well as the legacy of the other women in Isobel’s family, including her daughter. Which of the women in the family do you think were the most influential? What do you think Isobel and Margaret’s legacy will be?

11. On page 313, Isobel says, “Like Nat himself, the book was a truth within a lie, and a lie within a truth.” Consider Nat’s personal journey and his relationship with Isobel. In what ways is this statement true?

12. How did the end of the novel make you feel? What do you think comes next for Isobel and Margaret in their relationship and their story?