A school assignment prompts Pepper Ann to think whether she enjoys Christmas with her father or Hanukkah with her mother.
Following the holiday season, Pepper Ann gives an oral report in Mr. Finky's class on what she learned during the break. Pepper Ann celebrates Christmas with her father and Hanukkah with her mother and thus chooses to represent both holidays for the school pageant, much to Ms. Stark's concern. She learns that Nicky plans to be charitable for the holidays, but this backfires with her unwillinglly losing everything and not getting anything in return while Milo plans to travel to Hawaii to see his dad, but after his step-father injures himself, he has to fill in as a delivery person for his mom's bakery instead of going.
Pepper Ann starts to notice holiday overlap from both sides of her family which she feels is impeding on her practicing for the pageant. As the night of the performance comes, Pepper Ann comes out as a menorah, but accidentally begins singing a Christmas song; derailing the play. She begins to feel bad about it, especially after seeing Grandma Lillian hyperventilating during the performance and overhears her parents saying that "she" will have to choose by the time Christmas comes around. Her reflection convinces her that her parents are making her choose a holiday to celebrate.
Not able to make a decision, Lydia tells Pepper Ann to make a pros and cons list, though Pepper Ann is discreet on the subject. She proceeds to go back and forth between Lydia and Chuck's houses and celebrating both sides of Christmas and Hanukkah. While at a soup kitchen, Pepper Ann sees Nicky having lost her charitable spirit after a basket of muffins gets donated in her name and Milo helps out a group of homeless people and introduces them to Crunch Pod. Pepper Ann has an internal argument with the personifications of Christmas and Hanukkah and comes to the realization that she loves both holidays because of family and decides not to choose.
Pepper Ann returns home to tell her family that she will not decide on which holiday. Confused, they reveal that they were mostly concerned about Lillian as she was the one who needed to choose which doctor to go with after seeing what she thought was a rat; explaining her hyperventilating. Pepper Ann begins to hyperventilate over her mistake. Back in school Pepper Ann wraps up her story when Sherrie Spleen comes in to announce that Milo was the most charitable person during Christmas, frustrating Nicky. Milo wins a trip to Hawaii, but gives it to Nicky who admits that she had been selfish. Spleen splits the prize among them, with Pepper Ann shoehorning herself in, as all their families go to Hawaii.
- Kathleen Wilhoite as Pepper Ann Pearson
- Jeff Bennett as Christmas Tree, Grandpa Leo, Pink-Eye Pete
- Danny Cooksey as Milo Kamalani, Baron Von Gus, Wind
- Clea Lewis as Nicky Little
- Pamela Adlon as Moose Pearson
- April Winchell as Lydia Pearson, Sherrie Spleen, Grandma Lillian, Abriola Stark, Over Protective Woman
- Kenny Blank as Malik, Lamar Abudabe
- Tino Insana as JoJo Diggety, Earl
- Don Lake as Sherman Finky
- Maurice LaMarche as Chuck Pearson, Menorah, Colonel Delaney
- Kath Soucie as Cissy Rooney, Nicky's Mom, Grammie Pearson
- Susan Tolsky as Janie Diggety
- Jenna von Oÿ as Trinket St. Blair
"No way! Frosty! ...Oh well..."
- Only appearances of Grammie Pearson and Milo's biological dad.