Pepper Ann appears in a school production of Guess Who's Coming to Dinner, and P.A. worries that her mom (who is dating the handsome country line-dancer, Bernie) and her father (who now has a girlfriend) will embarrass her with their new dates.
Pepper Ann is starring in a musical adaptation of Guess Who's Coming to Dinner. Upon returning home, she learns that Lydia is going to see the play with Bernie. She gets a call from Chuck saying that he will be able to go as well. Pepper Ann's reflection informs her that this will be a disaster because Chuck does not have a date and him seeing Lydia with Bernie will make things awkward. Pepper Ann tries to say that the play has been cancelled, but Chuck sees right through it. Meanwhile, Nicky accidentally eats meat and decides to take advantage of it by going on a meat eating binge.
With the help of Milo, Pepper Ann puts out an ad for single women and picks the first one she sees, a clumsy girl named Sarah (pronounced Ser-ah "like the song"). Pepper Ann sees that Chuck and Sarah get along well, but suddenly gets a terrible thought of both couples fighting with each other over at the play and is hit with a new conundrum. Completely blowing Nicky's advice out of the water, she sends Lydia and Bernie to a diner to stall them and then has Chuck and Sarah sit behind a pole so that no one can see them.
Lydia and Bernie make it to the play while Chuck and Sarah decide to move to the front row. Sarah and Bernie meet and end up hitting it off while Lydia and Chuck see each other and casually greet each other. Pepper Ann sees them in the audience and faints. After the show, Bernie and Sarah leave together and Pepper Ann admits to her plans for the night. Lydia and Chuck tell her that she should not be worried about them as tonight was her night. Chuck offers that they eat out together with Nicky asking to join so that she can continue her meat binge.
- Kathleen Wilhoite as Pepper Ann Pearson
- Jeff Bennett as Dieter Liederhosen, Bernie Guberstein, Waiter, Additional voices
- Danny Cooksey as Milo Kamalani
- Clea Lewis as Nicky Little
- April Winchell as Lydia Pearson, Abriola Stark
- Maurice LaMarche as Chuck Pearson
- Megan Mullally as Sarah
- Cree Summer as Tessa and Vanessa James
- The title is a play on Guess Who's Coming to Dinner, which is the play Pepper Ann is starring in.
- This episode revealed that Nicky has not eaten meat for 6 years, meaning her last taste of meat was sometime before or during 1st grade.
- The song that Sarah is referring to is most likely "Que Será, Será (Whatever Will Be, Will Be)".