1. Lily set out to be a pediatric neurosurgeon but shifted her focus to research when Denny was young, in part because the schedule was more flexible. Later, Lily has an impressive career in scientific research. Is Lily a good scientist? Does it matter that research wasn’t her first choice of career? Did her career change make her a better mother? Might her life have been more satisfying if she’d stayed with surgery?

2. Denny’s parents, Lily and Charles, are professionals in the same field. Was this a strength or weakness of their marriage? Why didn’t they stay married?

3. When we first meet Maureen, she is suffering from severe agoraphobia—she’s afraid to go outside. She isn’t married or apparently close to her own family, nor does she have children of her own. Why does Denny get along so much better with Maureen than she does with Lily?

4. Denny chooses a different—some might say opposite—career path from her parents. What makes her unlike her parents? How do her parents’ choices and personalities influence her own?

5. Is Maureen crazy at first, or just depressed? What’s the difference? Did her sexual encounter with Jamie (the guy from the record store) cause her agoraphobia, or did her emotional problems make her particularly susceptible to the type of experience she had with Jamie?

6. Lily has a car accident that leaves her with a mild concussion and temporary amnesia. What, if anything, does Lily learn from her accident and its aftermath?

7. In the long run, does it matter that Lily misses Denny’s performance in Damn Yankees?

8. In Book Two, Lily calls Denny home to help her pack up their house in Bexley, the house where Denny grew up and where she lived with her mother and father before their divorce. Lily expects Denny to stay for a week and to make an effort to get to know her new stepfather, Phil. Why is Denny so impatient with her mother in this section of the book? Does Lily deserve it? How could Denny be doing a better job of being a daughter?

9. At the end of Book Two, after Lily and Phil have been fighting and Denny has been reunited with Maureen, Denny and Phil go out for ice cream and wind up kissing each other briefly. Phil is actually closer to Denny in age than he is to Lily. How do you feel about Phil and Denny’s kiss? Is it wrong? Should one of them have stopped it? What do you think was really going on there?

10. In Book Three, Lily and Phil are living together in New York City and trying to imagine what it will be like to retire. Why does Lily and Phil’s relationship last? What’s in it for each of them?

11. The director of Denny’s play is an extremely handsome former film actor named Sean. He’s a divorced father and comes from what sounds like a privileged background. Initially, Denny mistrusts him and it seems as if her reason for this is simply because he’s so good-looking. Are her instincts right or wrong? Where do you think those instincts come from?

12. Denny leaves California and the movie business to come to New York and direct her play. What’s different about New York? Why might it suit Denny better? Is it merely a coincidence that Denny and Lily settle in the same place?

13. At the end of the book, thirteen-year-old Luke has come to stay with Denny in New York. Will Denny be a good parent for Luke? Does it make sense for Luke to stay in New York? What will Denny have to change about her life that she hasn’t foreseen?

14. This book is full of families of various kinds, some makeshift, some formal; some functional, some less so. Who are the best parents in this story and why? Discuss some of the minor characters who sometimes act like parents—people like Denny’s drama teacher and her school principal in the early part of the story, and later, her agent, Luke’s grandmother, Sean, and even Simon (the guy at the library). What are some of the qualities that do and don’t make a good parent in this story?

15. This story is structured in three parts, each a different time in Denny’s life, with many years skipped in between. Why do you think Rachel Cline told the story this way?

16. One reviewer called What to Keep “chick lit for smarties.” Do you agree? How does What to Keep fit the category, and how is it unique?