- Why do you think Annie decides to close her life to new people?
- Annie has strong convictions about women in science and her worth as a chemist—but she doesn’t initially fight back when her company fires her for something that isn’t her fault. Why do you think this is? Do you think you would you have made the same decision under similar circumstances?
- Why is Annie was drawn to Harper, who is a “new person” and Annie’s complete opposite?
- 4. What was your first thought when Harper accidentally revealed her black eye to Annie? Were you surprised by what Harper later shares about her bruises?
- 5. Why do you think Annie reacts the way she does when she discovers Mo lurking behind her backyard? Is her primary motivation helping and protecting Harper, as she claims?
- 6. What was your first impression of Jon’s decision to go to Paris without Annie? Did that change after you learned why he’d gone?
- Annie says at one point, “Maybe time doesn’t so much heal wounds as weaken one’s convictions.” How do some of the beliefs she has at the start of the book evolve over time?
- What changes between Jon and Annie when they’re in Paris together?
- Annie says she’s put her dreams on hold because of her mother, who needs her. Do you think that’s actually true? Why or why not?
- What did you think of the way the novel ended? Did you think Annie would ultimately make the choices she did?
- Do you think Penny’s friendship with Jenny hurt her marriage with Sanjay? If so, how?
- Penny notes that “A single secret is like a lone roach. You know there will be more—it’s only a matter of when.” Do you think that’s true?
- In what ways did Penny’s childhood parallel Cecily’s? How did it differ?
- Why did Penny have an easier time sticking up for Cecily than herself, or anyone else in her life?
- At one point Penny notes that “close female friendships are built one secret at a time.” If that’s true, did what Jenny concealed from Penny mean the two women’s friendship wasn’t as close as she thought?
- Nancy Weingarten tells Penny to stop making everything look easy, and notes that most men act like things are harder than they are. Do you agree?
- Penny is rocked by the revelation that Sanjay has been attracted to another woman—even though she knows he handled the situation in what she feels is the correct way. What would you have done in her shoes?
- Do you think Penny’s brief attraction to her coworker, Russ, is a consequence of her grief—or because he does many of the things Sanjay hasn’t been doing?
- Penny fears that Sanjay will resent her if he has to curb his writing to make more money. Was this fear unfounded?
- Do you think radical honesty ultimately strengthened Penny and Sanjay’s marriage? Why or why not?
- Why do you think Maggie didn’t anticipate Adam leaving her?
- If you were in Maggie’s shoes, what would you have done differently after Adam announced he wanted a separation?
- How important was setting for Maggie? Do you think her decision to go to Rome, and later to temporarily move to Ann Arbor, played a role in her ability to heal?
- After Adam moves out, Maggie’s first instinct is to change the way she looks. But later, her appearance becomes less important. How did she change in other ways?
- What did you think of Charlie? Did your impression change over the course of the novel, and if so, why?
- At the beginning of the novel, Maggie feels invisible to the world. How much of that feeling do you feel was her fault—and how much was because of the way society treats women of a certain age?
- How does Maggie’s relationship with her children evolve? Do you think those changes are essential to the way she evolves as a person?
- Do you agree with Maggie’s decision at the end of the book?
- Why do you think James is drawn to Lou? Is it really love at first sight and therefore something he can’t control—or is his love a choice?
- How does James’ view of love evolve over time—and why?
- James’ mother says to him, “You do what you can with whatever you get.” This viewpoint seems to reflect his friend Wisnewski’s approach to life—which James suspects is the secret to happiness. Do you think he’s right? And do you agree with his mother?
- What role do names and nicknames play in this novel?
- James says that the difference between love and loss is so slight that it’s almost impossible to perceive. What does he mean by this? And does his fear of loss hold him back from fully loving others, such as Kathryn?
- In recalling his affair with Lou, James says, “It was a small series of choices that snowballed into a much bigger decision, which then became an outcome that none of us saw coming.” Do you think this is an accurate recollection of what happened between him and Lou?
- At the end of the novel, James tells Emerson she should trust Rob, even though he cheated on Lou: “Rob made many mistakes, as did I. They do not mean he isn’t a good man.” Do our choices make us “good” or “bad”? Why do you think both Rob and James failed the people they most loved?
- Why do you think Rob ultimately forgives James? How big of a role does James’ illness play in their reconciliation?
- Echoing the opening line of the novel, James later notes, “Every story ends with loss.” Is that true?
- What do you think was James’ purpose in writing this book for Emerson?
- Do you think Libby would have made the same decisions about her health if Tom had not made his confession on the same day she was diagnosed with cancer?
- Libby and her twin brother Paul have different personalities—and markedly different ways of dealing with crisis. Libby suspects that their personalities are at least partially a reaction to their mother’s death, but her father disagrees. Do you think personality is innate? How much of Libby’s sunny-side-up approach do you think is a reaction to her deep grief over her mother’s death?
- Was Shiloh’s announcement (that he, too, had once had cancer) unexpected? Did you suspect he was hiding something?
- Did you agree with the way Libby ended things with Tom? If you were in Libby’s shoes, would you have told Tom about your diagnosis?
- Have you ever gone through a near-death experience—and if so, did you realize it at the time?
- Tom and Libby were high school sweethearts. Do you really know who you are when you are 20? Should people get married so young?
- Do you think Libby’s pre-cancer behavior and ultra-sunny personality had a lot to do with why Tom waited as long as he did to tell her the truth about his sexuality?
- Milagros tells Libby, “Don’t look back too much; you’re not going that way.” Do you think she’s right? Is it a mistake to spend too much time thinking about the past?
-
This Won't End Well
-
- Why do you think Annie decides to close her life to new people?
- Annie has strong convictions about women in science and her worth as a chemist—but she doesn’t initially fight back when her company fires her for something that isn’t her fault. Why do you think this is? Do you think you would you have made the same decision under similar circumstances?
- Why is Annie was drawn to Harper, who is a “new person” and Annie’s complete opposite?
- 4. What was your first thought when Harper accidentally revealed her black eye to Annie? Were you surprised by what Harper later shares about her bruises?
- 5. Why do you think Annie reacts the way she does when she discovers Mo lurking behind her backyard? Is her primary motivation helping and protecting Harper, as she claims?
- 6. What was your first impression of Jon’s decision to go to Paris without Annie? Did that change after you learned why he’d gone?
- Annie says at one point, “Maybe time doesn’t so much heal wounds as weaken one’s convictions.” How do some of the beliefs she has at the start of the book evolve over time?
- What changes between Jon and Annie when they’re in Paris together?
- Annie says she’s put her dreams on hold because of her mother, who needs her. Do you think that’s actually true? Why or why not?
- What did you think of the way the novel ended? Did you think Annie would ultimately make the choices she did?
-
I’m Fine and Neither Are You
-
- Do you think Penny’s friendship with Jenny hurt her marriage with Sanjay? If so, how?
- Penny notes that “A single secret is like a lone roach. You know there will be more—it’s only a matter of when.” Do you think that’s true?
- In what ways did Penny’s childhood parallel Cecily’s? How did it differ?
- Why did Penny have an easier time sticking up for Cecily than herself, or anyone else in her life?
- At one point Penny notes that “close female friendships are built one secret at a time.” If that’s true, did what Jenny concealed from Penny mean the two women’s friendship wasn’t as close as she thought?
- Nancy Weingarten tells Penny to stop making everything look easy, and notes that most men act like things are harder than they are. Do you agree?
- Penny is rocked by the revelation that Sanjay has been attracted to another woman—even though she knows he handled the situation in what she feels is the correct way. What would you have done in her shoes?
- Do you think Penny’s brief attraction to her coworker, Russ, is a consequence of her grief—or because he does many of the things Sanjay hasn’t been doing?
- Penny fears that Sanjay will resent her if he has to curb his writing to make more money. Was this fear unfounded?
- Do you think radical honesty ultimately strengthened Penny and Sanjay’s marriage? Why or why not?
-
Woman Last Seen in Her Thirties
-
- Why do you think Maggie didn’t anticipate Adam leaving her?
- If you were in Maggie’s shoes, what would you have done differently after Adam announced he wanted a separation?
- How important was setting for Maggie? Do you think her decision to go to Rome, and later to temporarily move to Ann Arbor, played a role in her ability to heal?
- After Adam moves out, Maggie’s first instinct is to change the way she looks. But later, her appearance becomes less important. How did she change in other ways?
- What did you think of Charlie? Did your impression change over the course of the novel, and if so, why?
- At the beginning of the novel, Maggie feels invisible to the world. How much of that feeling do you feel was her fault—and how much was because of the way society treats women of a certain age?
- How does Maggie’s relationship with her children evolve? Do you think those changes are essential to the way she evolves as a person?
- Do you agree with Maggie’s decision at the end of the book?
-
Forever is the Worst Long Time
-
- Why do you think James is drawn to Lou? Is it really love at first sight and therefore something he can’t control—or is his love a choice?
- How does James’ view of love evolve over time—and why?
- James’ mother says to him, “You do what you can with whatever you get.” This viewpoint seems to reflect his friend Wisnewski’s approach to life—which James suspects is the secret to happiness. Do you think he’s right? And do you agree with his mother?
- What role do names and nicknames play in this novel?
- James says that the difference between love and loss is so slight that it’s almost impossible to perceive. What does he mean by this? And does his fear of loss hold him back from fully loving others, such as Kathryn?
- In recalling his affair with Lou, James says, “It was a small series of choices that snowballed into a much bigger decision, which then became an outcome that none of us saw coming.” Do you think this is an accurate recollection of what happened between him and Lou?
- At the end of the novel, James tells Emerson she should trust Rob, even though he cheated on Lou: “Rob made many mistakes, as did I. They do not mean he isn’t a good man.” Do our choices make us “good” or “bad”? Why do you think both Rob and James failed the people they most loved?
- Why do you think Rob ultimately forgives James? How big of a role does James’ illness play in their reconciliation?
- Echoing the opening line of the novel, James later notes, “Every story ends with loss.” Is that true?
- What do you think was James’ purpose in writing this book for Emerson?
-
Life and Other Near Death Experiences
-
- Do you think Libby would have made the same decisions about her health if Tom had not made his confession on the same day she was diagnosed with cancer?
- Libby and her twin brother Paul have different personalities—and markedly different ways of dealing with crisis. Libby suspects that their personalities are at least partially a reaction to their mother’s death, but her father disagrees. Do you think personality is innate? How much of Libby’s sunny-side-up approach do you think is a reaction to her deep grief over her mother’s death?
- Was Shiloh’s announcement (that he, too, had once had cancer) unexpected? Did you suspect he was hiding something?
- Did you agree with the way Libby ended things with Tom? If you were in Libby’s shoes, would you have told Tom about your diagnosis?
- Have you ever gone through a near-death experience—and if so, did you realize it at the time?
- Tom and Libby were high school sweethearts. Do you really know who you are when you are 20? Should people get married so young?
- Do you think Libby’s pre-cancer behavior and ultra-sunny personality had a lot to do with why Tom waited as long as he did to tell her the truth about his sexuality?
- Milagros tells Libby, “Don’t look back too much; you’re not going that way.” Do you think she’s right? Is it a mistake to spend too much time thinking about the past?
