Jenks begins his journey, meeting Chad, Kaylin and D-Real for the first time. Chad has autism, Kaylin has cancer, and D-Real is dealing with the recent murder of his brother, but all three of them inspire Jenks by their refusal to give in. CHAD After surprising Chad, a 21-year-old with autism who was a featured subject on WORLD OF JENKS: Season 1, the guys head off to Chad's favorite neighborhood spot: The Castle Fun Center, a place with miniature golf, go-carts and video games. En route, Chad says that he's extremely anxious about the near future, when he'll graduate from school and need to find a job for the first time. Chad and Jenks pay a visit to the home of Chad's girlfriend, Amanda, who is also developmentally disabled. Jenks observes the dynamics of their sweet and caring relationship while learning that Amanda doesn't consider herself to be a disabled person. On their way back to Chad's, Jenks announces that he would like to sleep in Chad's room tonight.

Jenks and his younger brother, Matt, are working out together at a gym. Matt gives Jenks a hard time about being out of shape. Jenks is grateful for his time with Matt because he doesn't get to see him much these days. CHAD It's Chad's senior prom. His girlfriend, Amanda, will be his date and he debates whether or not to kiss her. This would be Chad's first kiss. After picking out their tuxes, getting a haircut, and shaving, Chad and Jenks get dressed and discuss Chad's anxiety about prom. Since childhood, he's used a 'calming stick' that helps settle his nerves. Dressed, now calmer, and pumped for the night, Chad and Jenks head to prom in a stretch limo. On the way to Amanda's, Jenks and Chad make up a song about the upcoming night. They pick up Amanda at her house and surprise her with what will be her first ride in a limo. During their ride to prom, Chad's anxieties take over. He becomes obsessive about taking pictures and being late.

The episode begins with Jenks on his way to see Chad. In the car, Jenks talks with producer Kassie about growing up near Chad and Jenks' less than stellar dating history in high school. CHAD Only a week away from graduation, Jenks joins Chad for one of his last days at Westchester Exceptional Children's School. While there, Chad struggles and complains throughout his least favorite class: gym. Later, one of his teachers, Sylvia, explains to Jenks that while Chad is extraordinarily bright when it comes to maps and geography, he still struggles to read and write. While school has been tremendously beneficial to his development, it is apparent that Chad must continue to work on life skills such as buttoning his own shirt and tying his own shoes. During a counseling session, the reality of having to leave school and change his routine after graduation begins to hit home for Chad, and he talks about the anxiety he's feeling.

The episode begins with a montage of Jenks's college speaking engagements before filming began on WORLD OF JENKS: Season 2. During these appearances, Jenks talked about his first two documentaries, ROOM 335 and THE ZEN OF BOBBY V, and how he got to be on MTV. Jenks plans to use these experiences of speaking in public to help Chad, who must deliver a speech at his graduation ceremony. CHAD Chad's teacher reminds him that he must deliver a speech during graduation. He's not thrilled about it, saying that he doesn't believe in speeches, but goes along and enlists Jenks' help in writing it. The night before graduation, Jenks talks with Chad's parents, Mike and Sheri, about what life will be like for Chad after graduation. They are sad about him leaving school, but excited for the future.

D-REAL D-Real and the Turf Feinz give Jenks a new nickname, Whoa-J (derived from World of Jenks). Jenks likes this nickname much more than his old one, The Gentle Giant, which was given to him in elementary school because he was much taller than the other kids. D-Real gets a call from renowned choreographer, Flii Stylz (Usher, Chris Brown, J Lo) asking if he and the Turf Feinz will come to Los Angeles and meet him. The guys and Jenks fly out the next morning and Flii tells the Turfs that he saw their videos online and want to work with them. Afterwards they all go out to a dance club. The next morning on their drive to rehearse with Flii, D-Real tells Jenks that he has trouble accepting the peaceful vibe of the LA neighborhoods they're in. D-Real's gotten so used to Oakland's violence that it's easier for him to relate to death than to a smile. Then the Turf Feinz rehearse with Flii. They've never done choreography, which presents challenges, but Flii believes that they can learn.

CHAD Chad and Amanda have a date at the Woodstock Farm Animal Sanctuary but moments before Amanda arrives, Chad tells Jenks that he might want to break up with her. He doesn't appreciate Amanda's affection for "Justin Beaver" and her general "immaturity." He enlists Jenks' help in approaching Amanda with his concerns. After some hesitation and stammering, Chad politely describes his frustrations to Amanda who reacts graciously. Chad and Amanda are able to work out their problems without any lingering tension. They all enjoy the rest of the day at the farm. Back in Middletown, Chad's job coach from Occupations, Sean, has set up an interview for Chad at Alfonso's, a local pizzeria. Chad's anxieties are present, but he manages to charm and impress Alfonso and secures a trial run of the job.

CHAD Jenks explains that obsessive behavior is a part of Chad's autism, and that Chad's food fixation is making him gain weight. Jenks sits down with Chad's mother, Sheri, to discuss the reasons for Chad's weight gain and Sheri talks openly about her own struggles with this issue. Soon after, Chad has a doctor's appointment, and the doctor tells him and his family that Chad has diabetes. But if Chad can adjust his diet, increase his exercise, and lose weight, it is possible that the condition will subside. Later that evening, Chad's anxieties about his diagnosis push him to his emotional limits. To help his mood, Jenks stages a cooking show ("Cooking with Lorenzo") in Chad's kitchen as a way to encourage Chad to eat food that's better for him. D-REAL At a dance battle, a fight breaks out between Chonkie and members of a rival dance group. D-Real helps to diffuse the tension, but then gets into an altercation with a security guard and ends up threatening to shoot him.

CHAD In an effort to help Chad lose weight, Jenks wants to take him to the gym. While Chad would rather "die and rot in hell," he goes anyway. After a failed attempt at the treadmill and refusing to try free-weights, Chad finds success on the stationary bike. Chad, Jenks, and Chad's job coach, Sean, return to Alfonso's for a trial run at Chad's potential job. Alfonso puts Chad immediately to work: making garlic knots, folding pizza boxes, and stocking supplies. Chad quickly impresses the staff with his skills and charm. Alfonso offers Chad a job, which he excitedly accepts. Later, Jenks goes grocery shopping with Sheri, Chad's mother. She explains that she and Chad's father have adjusted their eating habits to help curb Chad's diabetes. She then reveals that the family is planning to move into a new apartment in a nearby town, but they haven't told Chad yet. Jenks worries because Chad doesn't do well when his routine is changed.

The Turf Feinz open for Mac Miller; Kaylin faces disaster; Chad struggles with the idea of leaving home.

Chad moves into his new home; Kaylin's clothes make it to the runway; D-Real organizes a dance battle.