Oscar ends up ruining Penny and Kareem's date night when shows up at the theater they are attending with a big cup of popcorn, making too much noise and neglecting to turn his cell phone off, emphasizing to Felix that Trudy asked him to look after the couple. Penny is so distraught over the event that she wishes she was grown up and living out the rest of her life in college. While scrolling through her phone, she sees an advertisement for an Al Roker Special and clicks on it, revealing Roker. Roker offers to make life better for Penny when she wishes to have her and her friends living the good life as sophomores in a co-ed college. Roker agrees, but not before giving Penny a contract stating that the effects will be permanent after a week.
A now nineteen year old Penny wakes up on the lawn of Peoria University, where she finds her friends, who have matured both physically and socially - Maya is an outspoken activist with dozens of supporters, LaCienega has a new car, Zoey had a glowup that leaves her almost unrecognizable, Michael is the leader of a cheer squad and on a basketball scholarship, and Dijonay has her hair puffed up. Kareem is also in the college too and his dorm room is right next door to Penny's and DiJonay's. Penny is generally committed to studying at first, but thanks to some coaxing from her friends, she ends up partying like there's no tomorrow at cost of her own expenses and her grades.
By the end of the week, Dijonay and the others hitch a ride in LaCienega's car to head back to the real world, not wanting to miss the last four years if their teenage lives, leaving Penny behind to her ultimate fate of being stuck in a 19-year-old body. Penny soon realizes that college is a lot harder than she realizes when she receives an eviction notices telling her that she fails as a human being. She learns from Myron, who has also been aged, that the "Big Guy" is the one in charge. Penny is horrified to discover that Roker is the dean. Even after asking Roker to send her home, he reminds her that she has a debt to pay, both personal and for the school. Only then, after selling a ton of items like a mixtape, DVDs, candles and incents, she will she be able to go home, but if she doesn't, she will remain in college forever.
None of the proprietors on the campus want to buy any of Penny's items and her keeping up with her studies gets even worse. She even tries to sell her books back, but gets $3 instead, enough for a Wiz Burger. Just as things start to look hopeless for her, a younger version of Oscar, who calls himself Big O arrives thanks to Dijonay giving him the contract to send him in, and he challenges Roker and four of his pint-sized henchmen to a basketball game. Following a short game and overcoming all obstacles, Oscar manages to win by default and Roker allows them to leave.
With everything back to normal, Penny and Oscar make up and they celebrate their escape by singing the opening number of Benedict.
- Kyla Pratt voices Penny Proud
- Tommy Davidson voices Oscar Proud
- JoMarie Payton voices Suga Mama
- Paula Jai Parker voices Trudy Proud
- Cedric the Entertainer voices Bobby Proud
- Keke Palmer voices Maya Leibowitz-Jenkins
- Alisa Reyes voices LaCienega Boulevardez/Freddy Frito
- Karen Malina White voices Dijonay Jones
- Soleil Moon Frye voices Zoey Howzer
- EJ Johnson voices Michael Collins
- Raquel Lee Bolleau voices Nubia
- Artist "A Boogie" Dubose voicesKG
- Asante Blackk voices Kareem Abdul-Jabbar Brown
- Logan Browning voices College Penny
- Jeremy O'Harris voices College Michael
- Karrie Martin voices College LaCienega
- Lena Waithe voices College Maya
- Desus Nice voices College KG
- Holly Winter voices College Zoey
- Jaden Smith voices College Myron
- Bresha Webb voices College Dijonay
- Al Roker voices Himself/Little Rokers
- Lamorne Morris voices Himself
- Roker references the events of Tween Town and Twins to Tweens in this episode.
- A clip of the latter episode is also seen
- LaCieniga mentions she's leaving with the others because she is not missing her quincinera. She celebrates it two episodes later in Raging Bully.