- If Side Trip was made into a movie, who do you see playing the roles of Joy and Dylan?
- Which character’s journey did you relate to more, Joy or Dylan? Discuss why.
- If you were in Joy’s situation, would you have given Dylan a ride? If you were in Dylan’s situation, would you have asked Joy for a ride? Was Joy too trusting to share a ride? Would you be willing to share a ride with a stranger?
- Can you relate to the guilt Joy felt over the loss of her sister? If so, how did you deal with it? What do you think about the way Joy handled her guilt?
- Joy makes many choices to honor her sister. Have you done something you wouldn’t normally do to honor someone you lost? Discuss what and why.
- What was your favorite side trip Dylan and Joy went on and why?
- If you chose a side trip, where would you go? Who would you travel with, or would you travel alone?
- What are your thoughts about Joy’s and Mark’s relationship? Do you think she really loved him or loved the idea of him because of Judy’s bucket list? Did his controlling nature bother you? Have you been in a similar relationship? If so, how did you handle it?
- What was your reaction to the big twist toward the end of the book? Were you caught by surprise or did you see it coming?
- If you could peek into your future, would you have made some decisions differently? What one decision have you made that you regretted? Share what you would have done differently and why.
- Have you ever lost someone and felt the need to finish a dream for them? Would you be willing to give up your own happiness to live the life you thought your lost loved one would have led?
- How does Dylan’s interaction with Joy dissolve the adamant feelings he holds regarding love and his profession?
- What’s on your road trip bucket list?
- Joy and Dylan agreed to three road trip rules: they don’t exchange last names, what happens on the road stays on the road, and if one of them wants to take a side trip, they both must agree. What would your road trip rules include?