1. If you took the title of the novel literally, what “secrets to happiness” would you say the book offers?

2. Holly is still hopelessly in love with Alex, who left her in order to start dating again. Do you think there’s a proper length of time to mourn a lost relationship?

3. What do you think of the character of Lucas? Is Holly’s relationship with someone so young inappropriate?

4. Holly’s writing partner, Leonard, has squandered the wealth that came along with his success. In what ways does money reign over the characters’ lives? Does it influence the way they act and interact?

5. Jack jokingly asks Holly whether the main character of her book “gets the guy” in the end. How do you think Secrets to Happiness might be similar to the book that Holly wrote?

6. Holly is outraged when Jack, a self-proclaimed Buddhist, orders a hamburger. Is her outrage justified? What do you think of Holly’s own struggle with morality?

7. When Holly adopts a dog with a brain tumor, Amanda accuses her of having a messiah complex. Do you agree? Is it possible that Chester rescues Holly as much as the reverse?

8. Betsy has a job normally held by women much younger than she is. What do you think of her own struggle for happiness? Do you think that age barriers can prevent people from being happy, or is happiness always possible?

9. Lonnie is a very different type of guy than Betsy usually chooses, as she freely admits. What makes her finally accept him as a romantic partner? What would you have thought of Lonnie as a potential date?

10. What do you think of the role religion plays in the book? How does it tie in with happiness?

11. Cathleen and Spence seem like an odd pair. What do you make of their relationship? Is there a logic to his dating her after being with Holly?

12. New York itself is a character in Secrets to Happiness. How do you think the story would have played out in another city? Are there inherent complications or advantages in life in a city like New York that add to or detract from relationships?

13. Amanda has “no regrets” about her dalliance with Jack. Is her attitude justifiable? Is Holly right to berate her?

14. At the end of the book, Holly has a new dog and more than a passing interest in Two Feathers. What do you think will happen between them, if anything?

15. In what ways is Holly similar to Emma Woodhouse in Jane Austen’s novel Emma? Are there other books that Secrets to Happiness reminds you of?