While swimming in P.E., Pepper Ann claims that she does not need to use the kiddy dive and wants to try the high dive instead. Unfortunately, Pepper Ann chickens out as she could not even climb the first couple of rungs and the fire department is called to get her down (Milo adds that she threw up in the truck). At lunch, Dieter invites everyone to his "unsupervised" birthday party. Pepper Ann at first likes the idea, but when Trinket mentions that kissing is involved, Pepper Ann becomes nervous. She agrees to go but admits to her reflection that she prefers a supervised environment. She tells Lydia about the party in an attempt to be prevented from going, but she ends up supporting her decision to go because as her mom she knows that life is always unsupervised.
Pepper Ann decides to practice kissing and after numerous failed, and comical, attempts is finally satisfied. She, Milo and Nicky arrive at the party together and end up having an average party there with festivities like pin the tail on the donkey and musical chairs. As soon as Dieter's mother leaves, he immediately sets up the game spin the bottle. As the game begins the bottle spins and supposedly lands on Pepper Ann. She gets up and admits that she hates being unsupervised and liked the more kid friendly games that they were playing and refuses. However, Nicky shyly reveals that the bottle landed on her and not Pepper Ann severely embarrassing the latter.
The party erupts when they learn that Dieter got the latest game console and Trinket calls spin the bottle "so last year" and asks if they can put on some music. Pepper Ann asks Nicky what it was like to kiss a boy and she admits that it was not that great as she had no emotional attachment to that person. Everyone leaves with Milo the only one who was disappointed (he tried to impress Gwen who was still into Dieter). Pepper Ann once again brags about being okay with kisses when her grandmother, Lillian, arrives and gives Pepper Ann a giant kiss on the cheek, freaking her out.
- Kathleen Wilhoite as Pepper Ann Pearson
- Jeff Bennett as Dieter Lederhosen, Additional Voices
- Danny Cooksey as Milo Kamalani
- Clea Lewis as Nicky Little
- April Winchell as Lydia Pearson, Mrs. Lederhosen, Grandma Lillian
- Kathy Najimy as Coach Doogan
- Jenna von Oÿ as Trinket St. Blair
- Kimmy Robertson as Gwen Mezzrow
- Lauren Tom as Alice Kane
"Wow, a dreidel!"
- This is the first time there's evidence that Dieter is German, aside from his accent. It's also the first time we find out who Klaus is.
- This episode starts the running "Lydia is baking" joke.
- When Dieter's mother leaves, she utters "I won't be back" in her thick accent. This is a reference to Arnold Schwarzenegger's famous line "I'll be back" from The Terminator.
- This episode continues the Milo x Gwen subplot first seen in "Crush and Burn".