Pepper Ann is unexpectedly invited by Sketch and her friends to an eighth grade party while adding "totes your amigs". Pepper Ann and her friends quickly deduce that she means "bring your friends" and are excited. She brings this up with Trinket and Cissy and asks if they are going, but admit that they are not because they do not need that pressure. Cissy adds that she would need to bring a date this time around, which concerns Pepper Ann as she has never asked or brought a date anywhere. Pepper Ann and Milo work together to interview possible candidates to be their date.
Nicky arrives and tells Pepper Ann and Milo that she has invited Stewart Walldinger. This news shocks Pepper Ann as she thinks that he is the least cool person at Hazelnut and therefore a terrible choice to take. While Milo tries to continue with the candidates, Pepper Ann does everything she can to deter Nicky from taking Stewart to the party, though all of her efforts comically fail. Pepper Ann is ultimately forced to take Milo as her date and tries confronting Stewart, only to learn that he is not a bad guy and even shares similar interests to her and leaves embarrassed when Nicky arrives.
On the way to the party, Pepper Ann tries to be upfront with Nicky and Stewart and inadvertently reveals their feelings for each other; cementing their relationship. Seeing how happy they are, she gives up and arrives at the party to defend Stewart's honor, only to learn to her embarrassment that everyone already knows Stewart and are cool with him. Sketch nevertheless, congratulates Pepper Ann for bringing her friends and she pats herself on the back, but loses her glasses; resulting in dancing with a hat rack she thinks is Milo.
- Kathleen Wilhoite as Pepper Ann Pearson
- Jeff Bennett as Pink-Eye Pete, Noah, Additional Voices
- Danny Cooksey as Milo Kamalani
- Clea Lewis as Nicky Little
- Karen Duffy as Sketch
- Meredith Scott Lynn as Tank
- Brittany Murphy as Poison
- Luke Perry as Stewart Walldinger
- Kath Soucie as Cissy Rooney, Additional voices
- Cree Summer as Tessa and Vanessa James
- Jenna von Oÿ as Trinket St. Blair
"Cool, a singing Dieter doll!"
- First appearance of Stewart Walldinger after first getting mentioned in "Vanessa Less Tessa".
- This episode originally aired as part of One Saturday Morning's "Stuart Day".
- When Pepper Ann and Milo are at Greezy 'n' Cheezy, the waiter tells them if they do not pay their check and leave he is calling mall security. When they leave, they are on the street.
- Nicky and Stewart become a couple.