The episode begins with Liz getting a call reminding her to attend her high school reunion. She initially refuses to go on the grounds that she would be uncomfortable and wouldn't have fun. Jack eventually convinces her that she has to go, if only to show up the people who used to tease her about being a chubby nerd.
Former GE CEO Don Geiss awakens from his coma and immediately asks to see Jack Donaghy. Jack excitedly believes that this will lead to his being named new CEO, but is devastated to learn that Don has decided that his work is not done at GE and that he will not be stepping down after all.
Tracy and Jenna get annoyed that Kenneth is getting more laughs in the elevator than they are. They eventually band together to get him to stop by doing HIS job since they feel he is stealing theirs. Jenna delivers him a sandwich while Tracy leads a studio tour. Kenneth immediately breaks down and swears he will never tell another joke on the elevator and never meant to hurt them. Tracy is satisfied with Kenneth's sincerity, but Jenna wants him to suffer even more for daring to entertain!
Liz gets to the reunion and makes her entrance, only to receive a hostile greeting from several of those in attendance. It turns out that Liz was actually an acid-tongued bully in high school who used carefully crafted insults to belittle her classmates as a defence mechanism. Jack gets stuck in the same small town because of a snowstorm and needs to blow off some steam due to the frustration of getting passed over for CEO. The town is dry, though (since 1885!) so he eventually ends up crashing the reunion for alcohol. He is charmed by the "simple" folk he meets and envies how happy they seem to be with their "simple" lives. When someone mistakes him for a former classmate, he gives in to the temptation to be someone else for the night. Everyone loves him as he regales them with tales of the old days that they supposedly shared, while Liz is universally despised in spite of her efforts to show them all that she is a nicer and kinder person now.
Her failure to win them over frustrates Liz and she lashes out again at everyone including Jack, with whom she is forced to share a closet for "seven minutes of heaven" after a game of spin-the-bottle goes awry. People get so annoyed with her that they want to humiliate her publicly by staining her with ink ("Carrie"-like, but more prime-time friendly). They stage an award for Liz for best school spirit and call her up on stage. Liz, perhaps sensing a trap, is hesitant but then is powerless to resist the allure of the restaurant gift certificate that goes along with the award. She steps up to the mic and the stage is set for the trap to be sprung, but Jack steps in at the last second and defends Liz, telling her former classmates that while she has her faults, she is a good person at heart. The mean-spiritedness drains from the room briefly, until jack is forced to announce (to avoid a paternity suit) that he is not actually a former alumni as he has led them all to believe. Before the crowd turns on both of them, Jack tosses some insults at them and he and Liz hightail it back to the GE private jet and back to New York.