1. Hannah has ongoing issues related to her archnemesis from high school, a girl by the name of Jacquie Goldfarb. Has there been a “Jacquie Goldfarb” in your life? If so, how did you get over any feelings of angst toward him or her?
2. Hannah's father is loaded with tall tales from their family's history. Does your family have any tall tales that have been passed down? If so, what are they?
3. Several awkward or embarrassing things happen to Hannah—and often in public places. What's the most awkward or embarrassing thing that ever happened to you in public?
4. Hannah is determined to win the favor of Bella Neeley, Galveston's most famous wedding coordinator. Can you relate to her people-pleasing ways? If so, how?
5. Hannah's family has an ongoing love affair with Bing Crosby and Bob Hope. Which of those two is your favorite, and why? Or is there another musician or song that has significance for you or that you find particularly romantic?
6. If you could capture the happiest moment of your life in a photograph, what would it look like?
7. Is there any such thing as a picture-perfect family or relationship? Why or why not?
8. Hannah's father claims that there's a long-standing feud between the McDermotts and the Kincaids. Has your family ever feuded with another? If so, how did you work out your differences?
9. Hannah's chief competitor is the guy she ends up falling in love with. Do you believe that would-be rivals could eventually fall in love? Why or why not?
10. At the Bing and Bob party, guests enjoy yummy British and Irish foods. What is your favorite British or Irish food? Or does your family celebrate food from a particular location or culture that has meaning for you?