1. Before the events of the book, Harriet and Wyn’s friend group has had a pretty seamless experience traveling together. What would you look for in an ideal travel partner? Have you ever taken a trip that put a relationship to the test?

2. Have you had a close relationship that’s spanned different phases of life? How, if at all, did those relationships change with time?

3. Do you tend to avoid conflict or face it head-on? Has this changed over time? If so, why?

4. Who out of this friend group do you most relate to, and why? Who do you least relate to?

5. If you were going to take a yearly trip to the same place, where would you go, and who would you go with?

6. So much of Harriet’s journey is about deciding whether or not to let go of a dream that no longer excites her, despite all the time and energy she’s already invested into it. Was there ever a time in your life when you had to make a decision like this? Did you make the same choice Harriet did, or did you decide to see it through?

7. Harriet and Wyn’s friend group plays a game where they talk about what they would do if they had another entire life to live. What would you do with a second life? Do you see yourself pursuing this in any way in your real life?

8. At the beginning of the book, Harriet is really “living for the weekend,” so to speak. Do you ever find yourself experiencing that? What are some ways you find joy and purpose in your day-to-day life?

9. For each character in the book, success and happiness look a little different. How do you define each?

10. Do you have a “happy place”? Is it an actual place, an experience, a person? Has it remained the same over the years, or does it change?