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What if your first love left town, without a word to anyone, days before graduation? What if, within months, he became one of the biggest recording stars on the planet, and every song he's famous for is about you? What if, after thirteen years of getting on with your life - walking past his face on newsstands, flipping past his image on TV, tuning him out on the radio - you get the call that he has finally landed back in your hometown for an MTV special two days before Christmas? What if you finally had the chance to confront him? What would you do? This is the dilemma faced by Kate Hollis, a woman on the threshold of her 30th birthday who discovers that the only way to become a well-adjusted, fully-fledged adult is to revisit 17.

1.      The authors alternate between Kate's present and her past. Why do you think they chose to tell the story this way?  Did you find it effective for showing how all the relationships evolved?

2.      Discuss Jake's parents. How does his mother's alcoholism affect his life? What about his father's abandonment? 

3.      Discuss the group of friends Kate and Jake are a part of and how their lives played out. What do you think compelled Kate and Jake to leave town, whereas all of their friends stayed? How has staying vs. leaving affected everyone?

4.      Kate's mom had an affair, Jake's dad had an affair, and Jake re-connects with Kate immediately after announcing his engagement to Eden. How does infidelity ricochet down the generations?

5.      Why do you think it takes so long for Kate's parents to talk to each other about what has happened? Do you think they blame each other or themselves for the condition of their marriage?

6.      Kate "got out of the car" (p. 214) and left Jake just as she always wanted to do. But when Jocelyn delivers the “what if I never left?” note (p. 218), Kate decides to go to him. Why do you think she does?  Have you ever given someone a second chance against your better judgment? 

7.      When Kate is swept into Jake's world, she discovers a lot of absurdity, from the team of assistants to Jake's nakedness before a performance.  The authors drew heavily on their own experiences working for celebrities.  How does our celebrity culture create the Jakes of this world? 

8.      Before you get to the New Year's interview, are you rooting for Kate and Jake to make it? Why or why not?

9.      What do you think of Kate's decision to leave Jake at the interview? Why do you think that was the final straw for her?

10.  Kate feels strongly that she needs to leave Jake regretting his entire existence. She has held onto this desire for twelve years. Why do you think she needs this kind of closure? How does she finally achieve it?

11.   Why does Jake not get in touch with Kate during all the years? He tells her that he thinks of her every day, and he Googles her (p. 115), but he never got in touch with her. What do you think prevented him from calling?

12.  Kate struggles with her own behavior when back in her parent’s home.  She knows she’s reverting to acting like a teenager. Why do you think that is?  How do you behave around your parents? 

13.  Talk about the theme of dedication.  Which relationship is the novel ultimately about? 
Photo by Melanie Dunea/CPi

Nicola Kraus & Emma McLaughlin are the bestselling authors of THE NANNY DIARIES and CITIZEN GIRL. They live and work in New York City. Visit

Photo by Melanie Dunea/CPi

Emma McLaughlin and Nicola Kraus are the New York Times bestselling authors of The Nanny Diaries, Citizen Girl, Nanny Returns, and the young adult novels, The Real Real and Over You. They are the cofounders of, a book coaching firm, and work together in New York City. For more information visit

  • Publisher: Simon & Schuster UK (September 4, 2008)
  • Length: 288 pages
  • ISBN13: 9781847395863