1. How did the book’s format influence your read? Were you surprised the first time that an email was forwarded?

2. This book is a scarily realistic portrayal of dating and communication these days. Do you think having the book be written by two authors made the book even more realistic? Why or why not?

3. Did you have a favorite character among Elliot, Madeline, David or Emily? If so, why did that person resonate with you?

4. Which email/text exchange rang the most true to you and your experiences? Please share that story!

5. Were you rooting for Elliot and Madeline to make it as a couple, or did you have reservations about the relationship from the beginning? How did watching their relationship unfold in real-time work for you versus just hearing about it from a third person narrator?

6. This book is just as much about modern friendship as it is about modern dating. Which friend are you in your inbox: the Madeline or the Emily; the Elliot or the David?

7. Did you see the ending coming? Were you happy about it?

8. Share your own nightmare dating story with your book club!

9. What do you think Madeline or Elliot could have done differently to avoid relationship hell? Or are relationships like theirs part of life?