The smelly stray dog gets in the car, disgusting Benji and Reggie. When Felix announces that he is adopting the dog, Benji argues that he should buy an expensive purebred instead. Felix insists that encountering the dog is fate. Reggie corrects him, explaining that it is determinism. He suggests that Felix read Baron d’Holbach. Felix offers Reggie an additional $1,000 to watch the dog for the day, and Benji adds another $1,000 if Reggie also gets the dog bathed. Reggie agrees but says they will also need to pay to have his car detailed. Felix names the dog Freebie.

At school, all the students stare at Felix and Benji. Benji tells Felix that they need to be completely honest with each other for the challenge to work. Aidan confronts Benji, complaining that Benji should have claimed he and Aidan found the wallet together. In the bathroom, Benji calls Little Italy Pizza and Pasta and orders 200 pizzas for lunch, arranging for the same order to arrive every school day until December 1.

The free pizza lunch is a huge success in the cafeteria. However, Benji notices that Alma Miranda, a girl he finds attractive, walks past without taking any pizza. He approaches her and offers pizza, but she politely declines, saying that she brought her own lunch. Benji sits with her and awkwardly presses the issue. Alma says that she just does not like to waste food. She jokingly asks if he gets another million dollars for every slice the kids eat, which makes Benji flinch. Unsettled by the one person who has refused his food, Benji leaves.

During an after-school basketball run, Felix and Benji are both made team captains. Felix’s team easily dominates and wins. After school, they find Reggie waiting with a completely transformed Freebie; the dog is now clean and groomed. Reggie hands Felix receipts for the vet, the dog grooming, and the car detailing; the total is over $700. Benji directs Reggie to drive them to the Grand Regency Hotel instead of to their homes.

At the hotel, the desk clerk’s attitude changes when she realizes who they are. Benji rents the Presidential Suite for himself, the dog-friendly Capital Suite for Felix, and a deluxe room for Reggie, paying for all of the rooms in full through December 1. A bellman shows them to Benji’s suite, which features a piano, a fireplace, and a life-sized marble horse statue. Felix sees that he has five missed calls from his mom, so he calls her back. She angrily demands his room number and announces that she is on her way up.

Felix takes Freebie down one floor to his own suite to meet her there. When she arrives, she furiously asks why he has a hotel room. Felix quietly reveals that he does not want to sleep on a couch anymore. His mom’s anger instantly turns to sadness, making Felix feel guilty. She accepts that the situation is temporary and sits down, petting Freebie.

Benji’s parents visit his suite and are not impressed, calling the expense a waste. To appease them, Benji lies about the cost and claims that Felix prepaid for it all, making it nonrefundable. He suggests that they use the time to remodel their home. At dinner, they argue over paying the bill and make him order healthy food.

Worried that his parents will ruin the experience and knowing that they will look at his online journal, Benji writes an entry framing the hotel stay as a practical decision to figure out how to invest the money wisely. He then goes to find Felix and discovers him heading to the hotel pool with Freebie. They go together, deciding to bend the rules that prohibit pets and unaccompanied minors. Benji strips to his underwear and jumps in. He convinces a hesitant Felix to let Freebie swim, and the dog paddles around in circles.

A hotel manager arrives, but instead of throwing them out, he makes an exception because they are special guests. Benji asks the manager to order room service for 9 pm, requesting two of everything from the menu. After the manager leaves, Felix and Benji splash each other in the pool, relieved and happy.

When Felix wakes up, he remembers that he and Benji spent $12,600 on in-app purchases for mobile games the previous night. In the hallway, Felix’s mom meets Reggie and is concerned about the boys hiring a chauffeur. Felix impulsively suggests hiring his mom instead, an offer she angrily refuses; she insists that she is not and will never be his employee.

In the car, Benji suggests that they get doughnuts since they are already late for school. Felix directs them to Downtown Donuts, where his sister Georgie works. Benji orders every doughnut in the store. While waiting for the order, Benji proposes that they all go to Disney World for the upcoming weekend. Felix tells Georgie to set up a standing daily order for 120 dozen doughnuts to be delivered to the school. He then invites Georgie to take the weekend off and join them at Disney World.

Benji and Felix hand out free doughnuts in the school hallway. Alma Miranda approaches, and when Benji offers her one, she politely refuses, saying that she already ate breakfast. Benji blurts out that turning down free pizza and doughnuts is not normal. Alma playfully challenges his definition of normal, then reveals that she is joking. She asks if he would donate food for the drama club fundraiser, which will be held on December 1, 2, or 3, pending confirmation from the drama teacher, Mr. Palomino. Benji eagerly agrees but stipulates that the event must be on December 1, joking that he is moving to Tibet after that date.

After school at open gym, Benji feels insecure about his basketball skills, as more talented kids are attending. In the car, Benji presses Felix for an honest opinion about his chances of making the team, but Felix is noncommittal. Reggie offers philosophical commentary on concepts like truth and the future. Frustrated, Benji suddenly notices Felix’s worn-out shoes and declares that they are going shopping.

At a sporting goods store, they go on a massive shopping spree. Felix is ecstatic about obtaining a new pair of Nike Air Flight 89s. They fill three shopping carts with apparel and gear, spending $15,579.69. When their purchases do not fit in the car, Benji decides that they need a bigger vehicle.

At a luxury car rental agency, the boys rent four vehicles: a Porsche, a Lamborghini, a Range Rover, and a Bugatti Veyron. The Bugatti is exceptionally expensive, with a daily rental of $20,000 plus a $100,000 security deposit and a $60,000 delivery fee from Miami. Reggie calls Benji’s spending hedonistic, referencing the ancient Greek philosopher Aristippus. Felix internally vows to be the opposite of a hedonist when the challenge ends. They drive away in the Range Rover.

Benji nervously asks Felix for permission to stop at Alma Miranda’s house and invite her to Disney World. When they arrive, Alma and her older sister, Ava, answer the door. Ava is friendly and excited, inviting them inside. Benji awkwardly invites Alma to Disney World. Ava eagerly accepts, but Alma is critical of their spending. When Alma learns about the Bugatti rental, she asks why they haven’t done something big and important with their money. Benji grows defensive and accuses Alma of being judgmental, then storms out. Alma tells Felix that she cannot feel sorry for millionaires, and Felix says their situation is complicated.

On Saturday, the group—Benji, Felix, Benji’s parents, Felix’s mother, Georgie, Michelle, Reggie, and Freebie—flies to Florida on a private jet arranged by a travel agent named Betsy. Benji is bothered by Alma’s rejection but tries to enjoy the trip. They arrive at the Magic Kingdom with VIP guides who allow them to skip lines. Freebie is taken to a doggy spa. Felix wants to ride on the Dumbo ride. Benji, who considers it a kiddie ride, reluctantly agrees but is surprised when he has a great time because of Felix’s infectious joy. Georgie and Michelle go off on their own, calling the trip a pre-honeymoon and thanking the boys.

The boys spend hours on rides at the Magic Kingdom and Hollywood Studios. After riding the Rock ‘n’ Roller Coaster, Reggie returns to the hotel to do homework. The boys stay until closing, wanting to watch the fireworks. On Sunday, they return to the parks, ride more attractions, and buy merchandise, including custom-built Star Wars-style droids. At 5 pm, they retrieve Freebie and head to the airport.

On the plane, everyone falls asleep except Felix and Benji. Felix says it was the best weekend of his life. Benji agrees, admitting that this trip was different because for the first time, he had a friend along, almost like a brother. He tells Felix that he is glad they are doing the challenge together.

After school, Felix and Benji shop online to spend money, turning it into a game with a five-minute timer for each purchase. Felix buys a $3,000 puppy perfume for Freebie. Benji buys a $72,000 vintage Hermès handbag. Mr. Trulz calls to verify each purchase. Felix buys a Tyrannosaurus rex skull for $250,000. Mr. Trulz argues that it is not art, but he allows it as a one-time purchase. Benji complains, so Mr. Trulz allows the boys to purchase one fossil each. Benji then buys a Triceratops skull for $65,000.

Felix’s mother arrives to take him to their apartment for dinner; Georgie will also be there. At dinner, his mom announces that she plans to go back to school for her nursing degree. Georgie suggests that their mom should quit her jobs and let Felix buy a house to support them. Felix protests that he can’t do that, and as his mother and Georgie begin discussing how Felix should invest the money, Felix begins to panic internally. His mom says that she will not quit working, but she reveals that she has given notice on their apartment; they will move to a smaller one at the end of December. Horrified at the thought of being unhoused when the money is gone, Felix awkwardly restrains himself from explaining his discomfort and simply asks his mother not to quit her job.

Georgie complains that she and Michelle cannot afford a big wedding. Felix offers to pay for the wedding at the Grand Regency Hotel, insisting that the event must happen before the end of the month. To justify this stipulation, he gives a weak excuse about securing a good deal. His mother is suspicious but does not press him. Georgie is thrilled and asks Felix to walk her down the aisle. She mentions their estranged father, Mark, by name, which makes Felix flinch. However, when he sees his sister and mother happy, Felix’s appetite returns.