Skip to Content

I Thought You Said This Would Work Book Club Questions

There is so much complexity and poignancy in this book that I Thought You Said This Would Work makes an excellent choice for any book club read.

I wish I had a club to discuss this with myself, just to dive deeper into a discussion about this book!

Dive Deep with Discussion Questions

If you do choose I Thought You Said This Would Work for your reading group, here is a list of questions I know I would personally love to get into.

These questions get pretty personal, but hopefully, lead to some really deep discussions. Wine is not discouraged before tackling them.

I Thought You Said This Would Work Book Club Questions

(Warning, if you haven’t read the book yet, these questions do contain spoilers)

1. We are introduced to the uncomfortable relationship between Samantha and Holly very quickly. Did you have any early ideas for why they might have fallen out?

2. Meeting Drew at the hospital seems to awaken feelings in Samantha she thought had long since died out as she put her daughter first her whole life.

In what ways can you relate (or not relate) to that rediscovery of self post-kids?

Source: Unsplash

3. Samantha talks about how flirting is easier in text messages because she can choose her words carefully and there is less pressure.

Are there other types of communication made better with technology? Made it worse? What’s an example of a conversation you wish you had had in-person vs. text, or wish you had had over text vs. in person?

Source: Unsplash

4. This road trip starts because of Katie’s need to have her dog with her to help her battle her cancer. Pets and their relationships overall get a lot of focus in the book.

Why do you think people bond so strongly with animals? Do you relate?

5. Summer essentially invites herself on the road trip and becomes an important part of the trio.

Have you ever had a stranger enter your life and just cause things to start happening? Or even had an important conversation with a stranger for a brief time while traveling?

Source: Unsplash

6. A lot of what happened between Samantha and Holly in the past was due to miscommunications and missed connections.

How do those make you feel? Do you blame either of them for not working harder to connect sooner? Do you understand where they are coming from?

7. Samantha says she never dated after her husband because she feared she wouldn’t be strong enough to be the one to leave a bad relationship.

Is there anything in your life you have stopped yourself from doing because of fear?

Source: Unsplash

8. The ending is quite abrupt after the end of the road trip. Did you find the ending satisfying? Surprising? Were there any topics you wish Ann Gavin had talked about more?

9. If you were going to gift this book to someone else to read, who would you give it to? Why?

Don’t have a book club yet? Why not start your own! Check out my article on How to Form a Book Club for tips on creating the ideal club for your lifestyle.

Did you read I Thought You Said This Would Work for your book club? What did you think? Leave me a comment below about how the questions and book worked for you!