1.) Though he was raised in Oriental, North Carolina, Dawson never felt he belonged there. Why not? Have you ever felt like an outsider or a misfit?

2.) Tuck is more of a parent to Dawson than his own father. What needs do Dawson and Tuck fulfill for one another?

3.) Growing up, Dawson tried to blend in with his family, going so far as to fail classes on purpose. Have you ever sabotaged yourself for the sake of others? Why does Dawson provoke such a strong reaction from his family?

4.) When Amanda’s parents threaten not to pay for college, Dawson decides it would be best if they broke up, saying, “If you love someone, you’re supposed to let them go” (19). Do you agree with him? What would you have done in Dawson’s position?

5.) As Amanda learns more about Tuck and Clara’s quiet life together, she concludes that they lived “in the middle ground, where contentment and love were found in the smallest details of people’s lives” (31). In your opinion, is this kind of life enough, or do people need excitement and passion to be happy? Where do you find contentment in life?

6.) Why does Dawson plead guilty in the trial regarding Dr. Bonner’s accident? Do you think his decision makes sense?

7.) Why is Amanda angry when she learns that Dawson hasn’t dated anyone in the past 24 years? How would you feel if an ex wasn’t able to move on after your breakup?

8.) Though they’ve been apart for more than 20 years, Dawson and Amanda’s feelings for each other are as strong as ever. Why has their love endured over the years? In your experience, is love eternal, or does it grow weaker with time and distance?

9.) Why does Dawson have the Bonners followed? Do you think he goes too far?

10.) Amanda admits to Dawson that she went to Tuck’s place to be alone after her father died. Why does Tuck’s home hold so much significance for Amanda? Are there any places you feel a strong emotional attachment to?

11.) Compare Abee and ted’s motivations throughout the novel. Why is it so important to Ted that he teach Dawson a lesson?

12.)  Why did Tuck plot to get Dawson and Amanda back together? Why did he wait until he died to do so?

13.) In his letter to Dawson, Tuck says that memories are funny thing because, “sometimes they’re real, but other times they change into what we want them to be” (192). Have you ever realized you were remembering the past differently than it actually happened? Do you think Amanda’s marital problems affected her memories of Dawson?

14.) Throughout the novel, Dawson repeatedly makes sacrifices for others. Do you think that he sacrifices too much? In what situations is it fair to put yourself before others?

15.) What do you think Amanda learns from her reunion with Dawson? How do you understand her choice at the end of the novel? What would you have done if you were in her shoes?