Gillian’s Do-Over – Questions for Book Clubs and Groups

  1. Portrait of thoughtful young woman working on laptopGillian, at age 46, never expected to be fired, but that’s what happens. How would you feel in her shoes? Do you agree with her neighbor, Lauren, that it’s high time Gillian did something, perhaps created a bucket list and started checking off the items? Why or why not?
  2. When her son, Quinn, takes it upon himself to help her sign up on a 40’s singles page, is he being pushy, or just extra caring? How would you feel if one of your grown children did the same for you?
  3. Matt Gordon’s life is complicated by his anticipatory grieving for his terminally ill wife and her dependency on him. What do you know about him, given his decision to quit the large law firm and open his own shop on the main floor of his home?
  4. Mo takes little time being attracted to Gillian, though she doesn’t feel quite the same for him, but he becomes a good friend. Should Gillian encourage him or gently let him down and move on? Why or why not?
  5. Gillian decides to create a trust for her future grandchildren. How much of this decision is related to her lack of knowledge about Bianca, Quinn’s fiance?
  6. What about Bianca is different from Gillian and why do you suppose Quinn is attracted to her?
  7. Gillian goes with Bianca and Quinn on a rafting adventure and has the misfortune of meeting yet another man who tries too hard to get close to her. What do you think of Quinn’s actions when he happens to come into the room when Herb has her surrounded?
  8. What is it about Matt Gordon that attracts Gillian’s interest? Is he simply “safe” because he doesn’t appear to react to her as Herb or those on-line guys have?
  9. Gillian gets caught up in helping Bianca and Quinn with their wedding preparations. In what way(s) does this serve to bring Gillian and Bianca closer?
  10. What do you think of Bianca’s parents? Her father’s new wife?
  11. When Gillian learns that Matt’s wife has died, she drops off a sympathy card and some flowers from her garden. Then, when she sees him in the park, she gives him a sympathy hug, which he misinterprets and is horrified that he has done so. His words send Gillian fleeing and Mo stops her from racing into the street. What about her reaction to Matt’s words shows how she feels about him?
  12. The local store that carries Gillian’s note cards and pictures gives her hope that she may have stumbled onto a new career. How would you feel in her shoes?
  13. Mo suspects Gillian likes him only as a friend, but he agrees to accompany her to the rehearsal, the rehearsal dinner and the wedding. What do you think of Mo when he steps in and prevents disaster at the rehearsal?
  14. Lauren, Gillian’s friend, admires Mo. Is it appropriate for her to dance with Mo when he came as Gillian’s escort? What do you think of Gillian’s encouragement of Lauren to see more of Mo?
  15. What do you think about Matt’s grown sons encouraging her to “get out there” and have a social life again? Are they looking out for their father or is something else going on there? How else might they help their father to get over his grief following the death of their mother?
  16. Gillian’s experiences with the on-line guys she meets appear to be a comedy of errors until she meets Hal, and she realizes he is not as he seems. How close to reality is this in the current on-line dating scene?
  17. When Quinn and Bianca insist on meeting with Matt after he has drawn up the trust to Gillian’s satisfaction, Matt takes both down a peg. Was he right in doing so?
  18. Gillian kisses Matt in his office and sparks fly for each of them. Then he comes over to her house and passion ensues. Should Gillian have invited him upstairs? Should Matt have followed her? Why or why not?
  19. Quinn claims he’s got everything backward and that he wants to start dating Gillian. Is he right to conclude that she deserves to be courted? How do you think his sons will feel about it? What about Quinn and Bianca?

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