Gather initial thoughts and broad opinions about the book.

1. What was your initial reaction to the ending, where the boys fail to win the $10 million? Do you think this was a more satisfying conclusion than if they had succeeded? Explain your answer.

2. How does McAnulty balance the fantasy of sudden wealth with the realistic middle-school problems the characters face?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. At the start of the story, Felix is a rule-follower, while Benji loves to “bend” the rules. Which of the two boys’ initial perspectives did you identify with, and why?

2. The friendship between Felix and Benji is tested by their newfound wealth, especially during the basketball tryouts. Think about a time a friendship of yours was challenged by a new situation. How did you and your friend(s) navigate it?

3. Which of the boys’ many purchases did you find to be the most outrageous or wasteful? If you were given the same challenge, what would you buy first?

4. Benji feels a lot of pressure to live up to his parents’ athletic legacy. In your own experience, how have family expectations influenced your own life choices?

5. What do you think was the most valuable non-monetary benefit that Felix and Benji gained from their experience? What cherished aspects of your own life transcend the concept of financial gain?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. How does the story use Felix and Benji’s home lives to explore the impact of socioeconomic disparity on the values and choices of young people?

2. What message does the novel send about financial literacy? Did the boys’ chaotic spending spree teach them anything meaningful about the value or purpose of money?

3. The fight at Georgie’s wedding goes viral, turning the boys into the “Billionaire Bratz” online. What commentary does the novel offer on social media, public judgment, and the power of a story to take on a life of its own?

Dive into the book’s structure, characters, themes, and symbolism.

1. How do Felix and Benji change by the end of the novel? 

2. How does Freebie’s accident force the boys to move beyond their focus on wealth?

3. How does the basketball court function to expose the boys’ different anxieties and render their financial power irrelevant?

4. Compare the premise of this novel to that of other stories, such as Brewster’s Millions? How does Millionaires for the Month adapt this idea for a contemporary, middle grade audience?

5. Several secondary characters, like Alma and Aidan, have different reactions to Benji and Felix’s spending. How do these interactions develop the novel’s examination of the difference between genuine friendship and opportunistic connection?

6. Is Laura Friendly a mentor who teaches a valuable lesson, or is she a cruel antagonist who puts two children in an impossible situation? Use examples from the text to explain your interpretation.

Encourage imaginative and creative connections to the book.

1. Benji and Felix pitch an idea for a mobile game based on their experience. What features would you include in the “Penny Doubled Challenge” game to make it both fun to play and educational for its users?

2. You have been tasked with designing a new cover for Millionaires for the Month. What imagery, symbols, or scenes from the book would you feature, and why?

3. At the end of the challenge, all the items the boys bought are repossessed. Choose one scene involving one of their lavish purchases and rewrite it from the perspective of an adult who witnessed it, such as Reggie, a parent, or a hotel employee.