Reader’s GuideVery Sincerely Yours by Kerry WinfreyDiscussion Questions:
1. Everett has always known what he wants to do with his life, while Teddy has never identified what she’s passionate about. Do you relate more to Everett or Teddy?
2. Teddy decides to do one thing every day that scares her. What kind of things have you done that scared you? Did you end up enjoying them?
3. Getting dumped by Richard pushes Teddy to make some big changes in her life. Do you think she would have made these changes if Richard hadn’t broken up with her? Have you ever gone through a seemingly negative experience that changed your life for the better?
4. Teddy and Everett get to know each other via email before they meet in person. Have you ever started a relationship with someone online? What do you think the benefits are of getting to know someone this way?
5. If you were in Everett’s position and had a chance to go to New York for a job like his, would you have gone? What might change your mind?
6. Teddy finds comfort in watching Everett’s Place, even if she isn’t the target audience. Do you have a show, film, or book that’s a metaphorical security blanket? Would you ever want to meet the creator?
7. Everett and Teddy had very different childhoods. How did their backgrounds and families affect their confidence in their own abilities and their determination to follow their dreams?
8. How do Everett and Teddy change one another’s trajectories? What do you think the future holds for their relationship?