The next section focuses on a series of misadventures in Noah's romantic life as he transitions into adolescence. His mother has always tried to give him advice about women and speak frankly to him about love and sex. When Noah is twelve, he has just started at a new school where Valentine's Day is taken very seriously. Some girls in his grade suggest he should choose Maylene, a girl with whom he sometimes walks home from school. At H.A. Jack, Maylene is the only colored student, and Noah is the only mixed student, so people assume they would be a good match. After going through the socially regimented process dictated by their friends, Noah asks Maylene to be his valentine, and the two of them kiss. Excitedly, he buys her a selection of gifts, only to arrive on Valentine's Day and find that Maylene has agreed to be the valentine of a white boy named Leonardo.
In Grade 8, Noah starts middle school at Sandringham, a huge school that is racially and economically diverse. Noah has experienced intense poverty growing up with his mother and has become more self-conscious about income over time. He doesn't fit in with the white kids because of his lack of money, and while he feels most comfortable with the poor Black students, they live in far-away neighborhoods, so he can't socialize with them outside of school. At lunchtime, the students rush to line up to buy food. Being fast, Noah begins taking orders from wealthy white students and taking a cut in exchange for standing in line to get their food for them. Although he still feels isolated and lonely, he now has a function within the social hierarchy of the school.
Being useful is important because Noah is poor, afflicted with bad acne, and wears ill-fitting clothes. He resigns himself to never having a girlfriend. He is friends with a girl named Johanna who is also close friends with a beautiful colored girl named Zaheera. Noah has a crush on Zaheera and imagines that if he can stay friends with her for years, he might someday be able to ask her out. He supports her as she dates a different boy, and Noah and Zaheera begin to talk on the phone regularly. One day, Noah unexpectedly learns that Zaheera and her family have moved to America, and that, worse, she had a crush on him but was always too shy to say anything. Noah realizes that he should have taken a risk, and he learns that regret is always worse than failure.
At the time when Noah is attending Sandringham School, he and his family have also moved to primarily white Jewish neighborhood called Highlands North. The neighborhood is quite far from school and also very isolated. The only kids he can find to befriend are the black children of the black domestic workers who sometimes live with the families they work for. One of these children, Teddy, also goes to Sandringham, and Noah and Teddy become close friends. They often go to a local mall together and they discover that they can easily steal chocolates from a small shop there. One day, Noah gets caught by a security guard and the two boys run off, chased by security. Noah is able to get away, but Teddy is caught. A few days later, Teddy's parents show up at the house and speak with Patricia. They explain that another boy was with Teddy, but that he won't say who and he insists it wasn't Noah. The next day at school, Noah is questioned because people assume that since he was Teddy's best friend, he might know about Teddy's other friends. Finally, Noah realizes why he is not being accused: the video footage of the theft and running away appears to show a white boy, and despite all evidence pointing towards Noah having been the other thief, no one can see past their conviction that they are looking for a white boy rather than a colored one.
As Noah gets older, he acquires a computer and CD writer and builds a business selling pirated CDs. He works alongside two other boys named Tim and Sizwe. Tim is connected to rougher black neighborhoods, accustomed to hustling and scamming. For example, he passes Noah off as a famous American rapper in order to make money from selling tickets to the fake performance. When Noah confides his disappointment at not having a date to senior prom, Tim promises to find him a beautiful date in exchange for a better cut of the CD sales. Noah is suspicious, but a few weeks later, Tim introduces him to a stunningly beautiful girl named Babiki who has agreed to go to prom with him. Noah is delighted, and he and Tim hang out with Babiki and her family a few more times leading up to the dance.
Excited, Noah is able to negotiate borrowing his stepfather's BMW, getting a new outfit, and getting a new hairstyle. However, disaster strikes on the night of the prom: Abel refuses to let Noah borrow the BMW, and by the time the two have finished arguing, he is an hour late picking up his date. He then gets lost driving to the location, and when they finally arrive, Babiki refuses to get out of the car. People gather around, commenting on her appearance, and Noah grows increasingly panicked. Finally, Sizwe points out that Babiki does not speak English. Noah finds this unbelievable, but then he realizes that he has never actually spoken directly to Babiki. Since no one at the dance speaks the only language Babiki knows, Noah finally gives up and drives her home in silence. Unexpectedly, she kisses him before she gets out of the car.
Noah's early experiences with girls are unsuccessful for a number of reasons. For one thing, he seems to lack confidence. He passively accepts that Johanna would prefer to be Leonardo's girlfriend, and he cannot imagine that Zaheera might return his feelings even though there are hints that she likes him as well. He is too shy to try to talk with Babiki, which leads to the confusion about what language she speaks. However, Noah's insecurity is also rooted in racial and socio-economic factors. Everyone assumes he and Johanna should be together simply because they resemble each other in skin tone. If Noah had more flexibility to choose a girl based on what they had in common, he might have found someone more compatible who would have returned his feelings. His sense that he is unattractive and does not have fashionable clothes also plays into his insecurity. Nonetheless, Noah does learn lessons from these early romantic experiences. He comes to see the value in being brave, and also in being genuinely interested in the women he dates.
While his love life is largely unsuccessful, Noah does establish himself as a shrewd entrepreneur. Growing up in relative poverty spurs him to be creative about how he can earn income, and his self-confidence and creativity push him to think outside of the box. He's willing to do whatever it takes and he has a natural ability to figure out what people around him want and then provide that. While there are economic benefits to running his small businesses, Noah's work also gives him a purpose and a sense of belonging. Because he lacks strong social ties, he focuses on making himself useful instead. Other students might not necessarily like him or feel that he belongs in their community, but he serves a purpose. Rather than dwelling on loneliness or a sense of isolation, Noah leverages his ambition, creativity, and intelligence to make the best of his situation.
While Noah's racial ambiguity can lead to isolation, it can also grant him privileges. Ever since he was a child, the fact that his skin tone approximates whiteness has allowed him to get away with things. In the episode shoplifting with Teddy, Noah sees the stark evidence of how race is used as a way to determine guilt and evidence. Because his appearance does not match the racial profile the police and school officials are working with, he is never even considered as a suspect. While Noah is shocked and somewhat guilty that he is getting away with the crime while his friend is being punished, he chooses not to confess. Because Noah has always had to be resourceful and look out for himself, he knows to avoid trouble at all costs, so he does not speak up.