Yesteryear

1. How did your opinion of Natalie change over the course of the book, especially as you learned more about her personal background, the origins of Yesteryear Ranch, and her transformation after Shannon's allegations?

2. Do you engage with accounts like Natalie's on social media? What's your relationship with them, are you an "Angry Woman" or a fan/sympathizer? How has reading this novel changed the way you view the real-life influencers on which Natalie is based, especially #tradwives?

3. Discuss the description of the first year of posts on Yesteryear Ranch's profile (chapter 26); did reading those stories change how you perceive posts on your own feed, including questioning what was actually happening in the moment that was captured, curated, and edited to look a certain way? Consider what the man from Caleb's chat room finds appealing about Natalie's profile: "Look at how hard this woman works. Look how exhausted and beautiful she is. This, my friends, is the true American dream" (p. 240).

4. Throughout the book, Natalie compares herself with her college roommate, Reena, whose views on motherhood/womanhood seem to be polar opposites of Natalie's, at first. Does Natalie sometimes long for, or admire, Reena's choices and views? How do you think Natalie's life would have progressed if she hadn't married so young like a "good Christian woman," dropped out of Harvard, and had to create her own security?

5. Similarly, when Natalie runs into her high school classmate at Target, she reflects: "Vanessa was liberated, sure, but I was happy. And it was such a shame, wasn't it? The way some women so willingly compromised every ounce of themselves in the name of building a life for themselves that they didn't enjoy" (p. 23). At the end of the book, do you think Natalie sees how she's followed that path exactly, or is she still blind to her own delusion? Does meeting with Reena for the interview reinforce the truth, or the fantasy, of a perfect life?

6. Early in their relationship, Natalie identifies that Caleb lacks motivation and clarity in his life, traits that deepen the rift in their marriage over time. What was ideal about their traditional gender roles being switched, Natalie, the more dominant "breadwinner," and Caleb, more passive and sensitive, for creating Yesteryear's success? How did it create problems when compared with the traditional roles they each played in the "Online" versions of themselves? Does this dynamic make Natalie's life more or less like Reena's?

7. How does Natalie and Caleb's marriage complicate the distinction between "man's work" and "women's work" in terms of what tasks and responsibilities are valued, paid, seen, and innate? Reflect on your own relationships' "rules" or examples among friends and family.

8. How does Caleb's personality motivate Natalie to clarify and adjust her own personality? Discuss the strategies and tools she learns about self-presentation, how to pretend without looking like you're pretending, from her online classes and from Shannon (lessons she passes on to Clementine). Is being in the public eye a sacrifice and challenge for her, or a fulfillment of something she's always wanted?

9. What do you think would have happened if Caleb had had the chance to run for office? Would his public performance have hurt or helped Yesteryear, their family, and America? Do you think their life would have been happier, easier, more "successful" if he'd become a kindergarten teacher as he had wanted?

10. Discuss Natalie's relationship with her father-in-law, Doug. How do they manipulate and exploit each other for their own gains?

11. How does Doug's campaign reflect the current state of American politics, as well as historical trends?

12. In her morning gratitude recitation, Natalie says that she is thankful for "the Inheritance" (with a capital I). What do you think she's referring to here?

13. Natalie's mother constantly berates her with the same refrain: "Why is it so hard for you to be kind?" What did "kindness" give Natalie's mother?

14. In the past/future version of Yesteryear, Natalie acknowledges that "for the first time in my life, I am being properly satisfied by a man." What do you think changed?

15. Compare Natalie's first set of children with her later children raised in the traditional ranch. Why do you think she doesn't recognize the latter as her own at first?

16. Discuss Natalie's criminal charges and the impact on her family.

17. Does Natalie's faith strike you as genuine throughout the book?

18. Was Natalie ever truly happy?

19. What do you think happened to Natalie after the Shannon incident?

20. Based on the ending, what do you think the author wants for her daughter and for women today?

Book Club Talking Points:
Yesteryear is a bold and conversation-starting book club pick. It blends psychological thriller elements with sharp social commentary on influencer culture, identity, and the pressure to perform a perfect life. This is the kind of book that sparks strong opinions, great debates, and deeper conversations about marriage, ambition, and what we choose to show the world.