The show begins with Liz arriving to work and Kenneth reading her messages – that company running the bike tour in South Carolina says no singles, her credit card called to make sure she's the one buying crème soda in bulk and her landlord called and he said, "It's not your toilet, it's you." The last message is from Gene from Liz's high school reunion committee inviting her to the reunion. Liz doesn't want to go but Kenneth, Tracy and Jenna are very excited about it.
In the same building, Jack helps a photographer take a picture of Kathy Geiss for the cover of the quarterly reports. She is recognized as head of the company while her father Don Geiss is in a coma. Jack thinks something is brewing when Kathy does something strange – she stares out the window and claws at the glass. That moment, Don Geiss wakes from his coma and asks for Jack.
Kenneth and Tracy are in an elevator filled with people. Tracy says a joke but no one laughs. When Kenneth cracks a joke, everyone laughs hysterically. Everyone but Tracy.
Jack comes into Liz's office with news – Geiss is awake and Jack will soon be CEO. He is very excited for his meeting with Geiss and thanks his lucky coin. After seeing Liz's reunion invite, he, too, insists that she go. Liz tells him of her unpleasant memories of high school as the school nerd. She has a memory of the most popular girl, Kelsey Winthrop, asking her a question, Liz mumbling something and the cool kids laughing. Jack says that she should go show them that "the ugly duckling turned into a vaguely ethnic swan." He even offers her the GE jet. Liz hesitates but he reminds her of the popcorn in the plane and immediately she "wants to go to there."
Later, Jack and Don Geiss meet. Geiss tells him that he was shaken out of the coma by a beam of energy that told him to continue working. Jack will still be Geiss's number two until Geiss dies.
At the studio, Tracy is sitting in his angry chair and yells at Grizz and Dot Com for not being there to laugh at his joke. He says that their job is to save him from embarrassment. They are going into the elevator with Kenneth so they laugh at Tracy's jokes.
Jack finds Liz in the hallway and tells her that he's still the number two. To drown his sorrows, Jack decides to fly to Miami after dropping off Liz. However, a snowstorm in Liz's hometown stops his trip to Miami.
Tracy is back on the elevator with Kenneth and a crowd. Tracy cracks a joke but everyone is disgusted except Grizz and Dot Com who "laugh." Again, when Kenneth cracks a joke, everyone begins to laugh - even Grizz and Dot Com.
In Liz's hometown, she walks into her reunion and struts to the bar. She sees the popular girl Kelsey and says hello. She mistakes Kelsey's reaction as surprise that Liz has become a "butterfly." In reality, Kelsey is surprised that Liz would come since she made life a living hell for everyone. There is a flashback to the same memory Liz had, but in this memory, Liz terrorizes the girl with her biting sarcasm. She then realizes that she was the mean nerd – her nickname was the "White Haven witch."
At the bar, Jack converses with some of her old ates. Liz finds him to tell him who she really was in high school. Another ate confronts her – she used to tease him about being gay. She insists it was only because she wanted to make it more comfortable for Rob to come out. But he insists he wasn't gay and introduces Liz to his wife.
Meanwhile, Jack chest thumps with his new friends and wishes he was them. At that moment, a ate mistakes Jack for a Larry Braverman and Jack decides to assume this new identity. All of Liz's ates like Jack or "Braverman" – he was apparently the cool guy at Liz's high school. Jack is then approached by Jessica who wrote Larry love letters. Jack pretends to know her and they share a moment.
Back at the studio, Tracy warns Jenna about Kenneth. She tells Tracy there is nothing to worry about – they are the stars here. However, when Jenna gets on the elevator with Kenneth, he tells a joke and a woman tells him that he should be on the show. Jenna then bursts into song – "Wind Beneath My Wings." Right after, Kenneth begins a sing-a-long of "99 Bottles of Bear." Everyone in the elevator joins in – except Jenna. She finds Tracy and they decide Kenneth is a monster and they need to stop him.
In White Haven, Jack and Jessica decide to play seven minutes in heaven. Jack spins the bottle and accidentally gets Liz. When they're in the closet, Jack says that they are not going to make out since that would be social suicide. He tells her that she hasn't changed – when he didn't get CEO, she made a joke out of the situation. She feels attacked and tells him that he's 50 years old and he printed out business cards for a job he would never have. Jack runs out of the closet crying – "why is she so mean?"
At the studio, Jenna and Tracy do Kenneth's job to prove that it doesn't feel good when someone else does your job. Kenneth cries and says he would never do anything to hurt Tracy and Jenna. He apologizes and Jenna asks him to keep crying so he won't ever make this mistake again.
Back in White Haven, Liz's ates decide to "Carrie" her. A woman announces that Lemon has won an award and a $50 gift certificate to Outback. Lemon needs to go to there. As she walks up Jack notices the bucket above Liz's head. Jack intervenes and defends Liz. Jack says that no one is perfect including him. Jack says he is proud to call Liz his friend.
Then, Jessica also thanks Larry and introduces him to his son. Jack immediately proclaims he isn't Larry Braverman. The audience boos them both as they escape to their jet to New York City.