1. The cover of The Ride of Her Life is unique. What does it say to you? In just looking at the cover, what type of story did you anticipate reading? What types of covers appeal most to you?
2. Friendship plays a big role in the story. What do you think has made Marguerite, Lilly, and Emily such fast friends? Have you ever been blessed with close friends like that? Share something about them.
3. After being reared in the Westing home as the daughter of household servant, much of The Ride of Her Life revolves around Lilly’s struggle with insecurity. What things led to her insecurity? In what ways can you relate to her security issues? Do you think women struggle with this more than men? Why?
4. Lilly, like most parents, wants what is best for her son. She wants him to have what she did not—a home. How important is a physical home to a child? As a parent, how do you deal with the desire to want something for your child/children that you did not have? How has this concept influenced our society and how we rear our children?
5. There were some unusual romantic scenes in this book –riding a camel, picking mushrooms, fishing with Levi, and visiting in the Squirrel Cage Jail. What are some of your most unusual dates or ones that you’ve heard about? How important do you think it is for a couple to share new and unique experiences? What would you like to do or where would you like to go on a date that you’ve never done before?
6. In The Ride of Her Life, there were several different mothers: Lilly, Evangeline Hart, Emily, Marguerite, Nick’s mother, and even Lilly’s own mother, Alice. How did each of these women parent? Who made the most difficult choices? Which is most like you as a mother or like your own mother? How is being a single mother today different than it was back then?
7. Lilly felt the Lord sent Eugenia to teach her patience. Could you have worked with a young woman like Eugenia? What things try your patience? Have you ever felt the Lord was teaching you something in a concrete way?
8. The roller coaster was a big part of this book. Roller coasters in 1906 were a far cry from today’s thrill rides, but how do you think people of that day felt about this new invention? What did the roller coaster symbolize in the story? How do you feel personally about roller coasters? Share one of your own roller coaster memories.
9. Nick says, “Trust is a fragile thread and easily snapped.” Lilly believes in God, but her trust in Him is shaken. What role did trust play in The Ride of Her Life? Has anyone ever broken your trust by a single action? How did you handle the situation? In today’s society, is trust valued? Why or why not?
10. Sean asks Nick about his prayers. He asks him if he’s praying a “God-doing-the-leading prayer” or a “wish-list prayer.” What do you think Nick’s answer would have been? What’s the difference between the two? In which way are you more likely to pray?