Book Club Discussion Questions and Guide for Flying Solo by Linda Holmes

1. Out of all of Dot's relatives and friends, Laurie is left to deal with cleaning out Dot's home by herself. She has four brothers, but they all claim to be too busy with their own jobs, children, and spouses to help with the task. Do you think it's fair that Laurie handles all of Dot's affairs on her own? Why do you think she does it?
2. Dot kept a lot of souvenirs and trinkets from her adventures that Laurie finds and uses to piece together parts of Dot's past. What items from your own adventures would you want your family members to find? What stories would they tell?
3. Why do you think Laurie is so determined to figure out the story behind the decoy duck? What does that say about Laurie and her personality? What would you have done if you were in Laurie's position?
4. When Matt first came to Laurie's apartment, she found him to be understanding, trustworthy, and harmless. What did you think of Matt when you first met him? In what ways did his true personality clash with his facade?
5. While they are sorting through Dot's things, Nick, Laurie, and June talk about the woes of online dating. What are your views on the subject? Discuss.
6. As a child, Laurie grew up in a noisy house with a big family and often escaped to Dot's for peace and quiet, and she continues to value that solitude in adulthood. How do you think Laurie's perspective on relationships was shaped by those around her?
7. Laurie and June have two very different perspectives about life, marriage, and family, and they sometimes disagree. Do you and your friends have contrasting views about big life choices? If so, how do you have those conversations with them about them?
8. Nick loves living in Calcasset and has spent his life devoted to the community there. Laurie, on the other hand, has affection for her hometown but no interest in moving back. Have you ever lived in a small town? Who do you relate to more in the story, Nick or Laurie?
9. Laurie ascribes her love for independence and self-sufficiency as reasons she enjoys and chooses to be single. Do you think getting married and having kids means losing that independence and self-sufficiency? Why or why not? If so, to what extent?
10. Did reading this book challenge any of the ways in which you traditionally view female independence, relationships, and the ways they're portrayed in mainstream media?
11. Discuss the title: How do you think the title relates to Laurie's decision at the end? When you first encountered the title, did you think it had positive or negative connotations? Did that view change (or not) as you read?

Unless otherwise stated, this discussion guide is reprinted with the permission of Ballantine Books. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.