Jann is shocked to discover her family have all made plans for the holidays that don't include her. With her assistant Trey (Tenaj Williams) for company, she reminisces about Christmases past – the good, the bad, and the humiliating – and it soon becomes clear there's more than one way to holiday. The special also showcases Arden performing classic holiday standards and features guest appearances by Michael Bublé and Bryan Adams.

Despite Jann's no drama rule for Thanksgiving, there is plenty of it when an amorous Michael Bublé shows up.

Jann becomes determined to figure out who anonymously donated a large amount of money to her crowdfunding campaign.

An eccentric wealthy couple offers Jann the money to fund her new album in exchange for promoting their gender reveal company.

Jann, Nate, Max, and Dave go on a romantic mountain getaway, but Max has a problem with Jann's new boyfriend.

Jann surprises everyone by going on a date with someone new: a much younger man.

Jann and Max spy on their mother Nora as she goes on a date.

When Jann's record label refuses to help her make a new album, she vows to find another way.

On the season premiere, Jann decides to take back control of her life and career, starting with hiring a personal assistant.