Kate is getting ready for Halloween with her mom, Rebecca (Mandy Moore), Kevin and Randall. Kate originally wanted to be a veterinarian, but as her mom hands her the costume accessories, she says she wants to be something else this year, something "pretty."
As Jack walks in the door and greets his family with his best evil, eerie laugh, Kate asks him for approval on the new outfit, not seeming to care how much work her mom put into the making of costume No. 1.
“Daddy, do I have to be a vet? I want to be Sandy from Grease," she says. "Pretty Sandy. Not tough Sandy.”
”Ok, you can be pretty Sandy," Jack replies. "Mom can handle that, right?”
Rebecca and Jack then speak privately, where she explains to Jack that he needs to "stop doing that with Kate," saying yes to anything she wants. She claims that by doing that, he's not preparing her for the real world, college or her 20s. He retracts by telling Rebecca she does the same with Randall, treating him "like a glass figurine."
We see that's true when Kate and Kevin go trick or treating with their father, while Rebecca takes Randall on a separate route. Jack is confused when Kate runs off to meet up with a boy unexpectedly, but Kevin quickly fills him in:
Kevin: "She's gonna ask Billy Palmer to go through the haunted house with her, and if it gets scary, he might hold her hand. She has a crush on him."
Jack: "Come on, that’s ridiculous. She’s 10.”
Kevin: “It's ridiculous because he’s Billy Palmer. He’s almost as popular as me and no way is he going to hold her hand."