Book Club Discussion Questions

Questions and topics for book club discussions 

* Chris is available for “author chats” with your book club. Arrangements can be made for both in-person and virtual meetings. To schedule, please email

1. In Chapter One, John travels to Las Vegas for the job of his dreams, but has no idea what the opportunity is—only that the offer came from his childhood friend, Mark. What does this tell you about John and his feelings toward his friend?

2. When John is shown the video for prospective clients in Chapter Two, it’s revealed that Timeless Arts’ mission is to observe historical and artistic events of the past. If you were given the choice of visiting any event in the past, where would you go and why?

3. Lillian explains that prior arrangements must be made for each Observation, and the arrangements could change depending on the number of clients traveling to an event. In her preparations for Don Giovanni, Lillian had met Casanova multiple times, but Casanova only met Lillian twice. What are the potential dangers this kind of arrangement?

4. How does the story deal with the problem of time-travel paradoxes?

5. Timeless Arts employees are reminded multiple times not to time travel with any modern items, yet all of them break this rule. Why is it not strictly enforced?

6. After meeting Alexander Hamilton, John laments Hamilton was the “shell of the man” he expected—presumably because Hamilton’s chance for distinction never materialized. Do you feel talent will always rise, or are we shaped by the circumstances surrounding us?

7. In order to save George Washington’s life, John and Mark face the prospect of joining the British army they know will be decimated in battle. Were there better options that might have been safer than subjecting themselves to the dangers associated with the battle?

8. Mark reminds John not to befriend any of the other soldiers because of the temptation to protect their lives and possibly change history. What was John’s response? How would you respond in a similar situation?

9. When John returns to his own time, Harrison Meade acknowledges he’s always known about Washington’s vest prompting John’s realization that his experience was always part of history. Had Meade told John beforehand, do you think John would have made the trip to the past?

10. John encounters Gisçard twice during his travels. What might have happened if they had never crossed paths?

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