1. Take a Chance on Me opens with a letter Ingrid writes to her oldest son, Darek, expressing her concerns and prayers for him. Do you think Ingrid should have given Darek the letter—or that she should at some point in the future? Why or why not? How do you work through your prayers or worries, whether for others or for yourself?
2. In her letter, Ingrid tells Darek, “You never seemed to question the beliefs your father and I taught you. Perhaps that is what unsettled me the most, because without questioning, I wondered how there could be true understanding.” Do you agree that beliefs need to be tested, questioned, to be fully understood? How do you see each of the main characters—Darek, Ivy, Jensen, and Claire—questioning their beliefs over the course of the story? What are the results?
3. As “the most ineligible eligible bachelor in town,” Darek frequently wishes he could start over without the baggage of his past. What circumstances keep him from moving on? Have you ever wished for a new start? Darek sees a relationship with Ivy, a woman unburdened by his history, as the key to his second chance. What would a second chance look like in your own life? A new job, a move to a new place, a new relationship?
4. After growing up in the foster care system, Ivy is used to being on her own; she’s determined to stay impartial in her work and cautious in her relationships. But at the same time, she longs to belong somewhere, to be part of a family. How do these conflicting desires play out in her actions?
5. Jensen sees himself as a pariah in Deep Haven, unforgiven for his role in Felicity’s death. How does his perspective change by the story’s end? Have you ever had to reconsider a long-held belief about yourself?
6. Darek and Jensen were best friends from childhood, but even before their friendship broke apart, they competed for hometown glory and for Felicity’s affection. Similarly Claire is devastated by Felicity’s death but still resents the attention her friend always got from Jensen. Is there anyone in your own life with whom you’ve had a complicated friendship—one tainted by jealousy or rivalry? How did you handle that dynamic?
7. After Felicity’s death, Darek gave up his dream of firefighting to work at Evergreen Resort. Years later, he’s determined to help the family business survive but still angry over the way his life has turned out, sticking him in a role he never wanted. How do Darek’s feelings for the resort change over the course of the story? Have you ever felt burdened by a family legacy? How do you feel about it now?
8. Claire watches as two of her friends get engaged, happy for them while at the same time feeling pain over the inertia of her own life. Why do you think Claire feels so stuck? Have you ever felt as though life was moving forward without you? What did you do about it?
9. As a single father to Tiger, Darek feels he’s doing his best to raise his son on his own. But in others’ eyes—particularly Nan Holloway’s—Darek appears to be negligent or incapable of parenting well. Whose point of view did you agree with? What do you think Darek was doing right as a parent? In what areas did he seem to need help?