All The Pretty Places is based on my ancestry, on stories I’ve heard from birth. Are there any family stories or figures that have captivated you? Why?

Sadie starts out wanting to run the nurseries simply because it is her passion, but later, realizes that realizing her dreams could also serve a greater purpose. Has this ever happened to you?

If you could choose the professional path of Sadie, Charles, or Freddie, who would you choose and why?

What surprised you most about the book?

You get to transport back in time and visit the Brundages’ rose garden, the Finks’ pink garden, or the Goulds’ rooftop garden. Which do you choose?

At one point, Sadie must decide to forego her own happiness for the sake of others. What does it take to make such a decision? Have you ever had to make one?

What is your favorite flower? Why?

Nature has a profound impact on our wellbeing. Why do you believe that is?

Why do you think Sadie hadn’t realized how much natural beauty was restricted from the poor before? What do you think truly caused her to take action to make natural beauty accessible for all?

Who was your favorite character? Least?

1. Like all of us, Dorothy had to fight deep seeded insecurities throughout her life and was ultimately able to (mostly) rise above them. What surprised you most about her struggles/triumphs? Can you associate with her journey?

2. The Greenbrier Resort has a large cast of principal and supporting characters. Who did you most associate with and why?

3. How does The Greenbrier serve as both a character and a metaphor for Dorothy’s life?

4. Even in the 1940s timeline, female business owners were rare and divorce was almost always considered the woman’s fault. Why were these views common during this period in history? Do you think these issues have been settled over time or do you think that they’re still prevalent today?

5. The true connection between Dorothy and Enzo was started because of their mutual desire to shake the shackles of their past and win freedom. Do you believe that they both ultimately achieved what they were looking for? Why or why not?

6. Societal expectations always seem to follow Dorothy like a shadow. Discuss the influence of these expectations on her decisions. Have peers or societal pressures ever affected the decisions you’ve made? Have you ever decided to go against the grain or walk a different path than what was expected of you? What was the outcome?

7. The structure of the book—alternating past and present—is used to create tension. In what ways does the past interfere with the present?

8. Dorothy’s relationship with The Greenbrier is deep and important. Do you have a particular place like this? If so, what has made it so special to you?

9. Dorothy’s love interests—Enzo, Warren, and Lee—are so different and yet she finds honorable characteristics in them all. If you were to go on a date with one of them, who would you choose and why?

10. Later in life, Dorothy finds that her closest family isn’t necessarily her actual family or even her friends, but her employees—the family she chose herself. Have you ever found family with people who aren’t related to you? If so, what made these relationships vital to you and why were they important to Dorothy?

11. If you could attend one event detailed in the book, which would you choose and why?

12. The story is told against the backdrop of several important historical events—the Gilded Age, the World Wars, and the Depression. How do these events impact the characters? Could this story have been set in another time?

13. Share a favorite quote from the book. Why did this quote stand out to you?

14. If you could read this same story from another person’s point of view, who would you choose?

1. Secret Sisters is set during the Gilded Age, a time period I love because social boundaries and norms were on the cusp of great change. What did you enjoy about this period? What do you dislike about this period?

2. Beth, Lily, Mary, and Katherine are all studying subjects that are very unconventional for women of the time. What surprised you most about their struggles/triumphs?

3. Secret Sisters has a large cast of principal and supporting characters. Who did you most associate with and why?

4. There are several viewpoints examined in this novel, best seen in the contrast between Grant and Beth. Why were these views common during this time period in history? Do you think these issues have been settled over time or do you think that they’re still somewhat at odds today?

5. The characters’ parents play a cloaked but active role in their lives. Discuss the influence of each main character and their parents. If you feel comfortable to discuss this, talk about your own parents. Have you embraced their ideals or decided upon a different path?

6. Beth, Lily, Mary, and Katherine are all very different. Who did you enjoy most?

7. All of the characters in the book are chasing their dreams. What challenges have you overcome to chase yours?

8. Grant and Will are so different and yet Beth finds honorable characteristics in them both. If you were to go on a date with one of them, who would you choose and why?

9. Beta Xi Beta is based on the founding of the 27 panhellenic sororities, a part of history that is relatively unknown to the general population. What surprised you most about how these organizations were formed?

10. Co-education was still a controversial topic at the time of the novel. Many colleges in the north and south were sex-segregated, while those in the Midwest were often sex-integrated. Why do you suppose some people believed it best to separate men and women?

11. The novel concludes with many promises for the characters’ future. What would you like to see happen to the characters in the following years?

12. Overall, what did you enjoy most about the story?

1. What did you enjoy about The Fifth Avenue Artists Society? Which character did you most associate with?

2. The Loftins often speak of their family history, recounting stories of their ancestors. What is the most interesting story of your family?

3. All of the women in the novel are strong in their own way. Who is your female role model? Why? What is it about that person that makes them strong?

4. Discuss the triumphs and tragedies of Ginny’s life. How did they shape her? What do you feel for her?

5. The relationships between Ginny and Charlie and Ginny and John are both complex. What are the strengths of each relationship and the pitfalls? Can you think of real-life examples of relationships like these?

6. Art is a major force for nearly every character in the novel. Discuss each of the siblings. Why is their particular art so important to them?

7. When Ginny first encounters the artists society, she is shocked that men and women are sharing their ideas and art. Can you think of some changes that allowed this sharing to become more acceptable in our country today?

8. Discuss the goals of each sibling. How did these goals drive them?

9. John and Franklin are both active participants in the Optimism Solution scandal. How did their involvement change your perception of them?

10. Societal norms of the Gilded Age were much different than they are today. If you could restore some of them to today’s world, would you? If so, which ones? In the same manner, which of them are you glad to see extinct?

11. What is the role of the artists society in the novel? How does it shape each character?

12. What will you take away from The Fifth Avenue Artists Society? Will any aspects remain with you?