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

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.