3. When Carmen and Eliza look for a potential fake fiancé at Dorrian’s in chapter 3, Carmen describes Eliza’s ideal as “eligible bachelors who would look amazing on Instagram and are dumb enough to not question whatever scheme you’re cooking up.” Do you think Blake meets these criteria?

4. Eliza and Sophie are inspired to open their own business by their parents, who own a boating store in Maine. How do you think opening a small business has changed since the time when their parents did so?

5. How do you think Sophie feels about Eliza being the face of the brand, especially when Sophie worries Eliza may hurt the business in the long run?

6. Eliza’s many Instagram followers are a significant presence in this novel. In chapter 10, she claims that, “It’s good for customers to see that I’m a real person who eats cheese and drinks wine, too. It helps them feel like, you know, they know me. And that translates directly to sales.” How do you think having so many strangers following her life affects her? Is Eliza using Instagram as a tool for promoting her business or as an outlet for herself?

7. When Sophie asks Eliza for a large sum of money for her IVF in chapter 11, she tells Eliza, “You’re getting everything you want.” Do you agree? Why or why not?

8. Eliza wrestles with her feelings for Blake for much of the book, saying in chapter 17, “It’s hard for me to wrap my head around how I feel about Blake. . . . I don’t doubt that I have feelings for him, but I do doubt that they match the strength of his feelings for me.” Do you think her ruse hinders her ability to express her feelings for him?

9. Blake and Raj represent two opposites: the guy who looks good on paper and the guy Eliza’s drawn to in real life. Think about the way her relationship with each progresses. How do they differ?

10. Why do you think Eliza keeps Blake in the dark about the fake engagement and wedding for so long?

11. In many ways, Eliza’s ruse picks up steam when she’s offered free or sponsored products for her wedding. Do you think her sponsored wedding is something she would have picked for herself?

12. Sophie and Eliza are very different people, and yet they share a close bond as sisters and business partners. How is their closeness tested throughout the novel?

13. When we talk about dating in the digital age, we often talk about dating apps. How do you think other forms of social media—like Instagram—influence the way we find and fall for partners?