Louis tries to help Jessica with holiday planning; Eddie, Emery and Evan find themselves on the naughty list for breaking an expensive gift.

With a little help from Louis' business advice, Jessica lands her dream job as a private school dean. Yet, after learning she was the token diversity hire, she quickly discovers a way to flip the script and use her title to make a difference. Meanwhile, Eddie and Emery teach Evan the hard way that it's okay for the brothers to have their own "things" at school.

Jessica grapples with her vision of the future as the boys are each realizing what their own goals.