Printable Book Club Questions for An Anonymous Girl by Greer Hendricks and Sarah Pekkanen

When the book begins we learn that Jess is a makeup artist in NYC. She says that her job is to create transformations but it’s only a temporary fix and people will revert to their former selves. What do you think she meant by this? Why do you think she chose to work in that field?
Why did Jess decided to participate in the study initially? Would you participate in a study like this? Why or why not?
The story is told in the first-person perspective of Jess and the second-person for Dr. Shields. What did you think about this writing style? How did it help build suspense?
Jess tells her parents she’s still involved with doing makeup for Broadway shows when in reality she’s a freelance artist who does makeup for ‘random’ people—going on a night out or celebrating an anniversary. Why did Jess hide the truth from her parents? What was she afraid of?
Jess believes that Dr. Shields is an older man and is shocked to find out that in reality, she’s a successful woman in her 30s. When she finds out Jess says:
“I believed I knew the person I was writing to: a thoughtful, compassionate man. But learning Dr. Shields is a woman causes me to rethink all of my questions. And all of my answers. What does this flawless-looking woman think about my messy life?”
Why do you think Jess felt this way? Do you think Jess would have given different answers if she would have known all along that Dr. Shields was a woman? Do you think women are conditioned to care more about what other women think of them compared to a male’s option of them?
Dr. Shields starts to manipulate Jess by paying her a large sum of money for the sessions and buying her gifts. Are you surprised she didn’t ask more questions about Dr. Shields’s study or do you think she was blinded by the money and attention? Why do you think she felt comfortable enough to tell Dr. Shields’s about what really happened to her sister Becky?
We learn more about the dynamic between Dr. Shields’s and her husband Thomas. She reveals that he was unfaithful to her and they are somewhat estranged. What did you think Dr. Shields’s motivations? Did that change at all as the story went on?
Part Two begins with Dr. Shields tasking Jess to flirt with a man at a hotel lobby. Why do you think Jess went through with it?
The event causes Jess to tell Dr. Shields her story of assault. Dr. Shields suggests that it might be a reason why Jess isn’t interested in a serious boyfriend. She says: “it isn’t uncommon, when a woman endures an assault like you did, for her to withdraw, or to change her relationship patterns.” What did you think about this section?
After the traumatizing make-up sessions that Dr. Sheilds’s set up for the experiment and seeing a woman get hit by a car outside a museum, Jess is feeling on edge. She decided to hook up with the guy she met museum. She says: “With him, I can just be an anonymous girl.” What did she mean by that?
What was the turning point for Jess to start to suspect that Dr. Shields’s was manipulating and using her? Why did she trust Thomas? Did you trust him at first? And on the flip side, when did Dr. Shields start to suspect that Jess was hiding things from her?
What did you think about the revelations of April (Subject 5)? How were her story and Jess’s similar?
Why did Thomas fabricate the affair with Lauren, the boutique owner? Were you surprised Dr. Shields’ knew the truth about her husband and April all long?
Dr. Shields believes that despite all the differences between herself and Jess that the most important pivot points in their lifetimes echo. Do you agree the women were connected that way or not?
When did Jess start thinking several steps ahead like Dr. Shields always does?
What did you think about all the reveals—Dr. Shields giving the pills to April and manipulating her and her final action in the end?
Let’s discuss the epilogue. What happens next for Jess?
If they make this into a movie or TV series, who should play all the lead parts?