'Twas the Date Before Christmas

This Christmas, Jessie Chamberlain feels the need for stability as she has begun dating again via a dating app as the first Christmas "post-Shaun", thus far all her dates having been duds. So when her mother Laura tells her that she and Jessie's Aunt Lilly are scaling back their family's all-day Christmas Eve tradition, domineering Aunt Lilly the day's organizer, Jessie, solely in a move to keep the Chamberlain Christmas Eve as is this year, lies to her mother saying that they can't scale it back as she has invited a plus 1 telling him all about that tradition. Thus, Jessie pivots her online profile looking for someone who will agree that their first date will be to attend that Chamberlain family Christmas Eve and all its craziness, she believing that anyone who answers such a dating request being just off-kilter enough to be a potential longer term match. The one person who answers is Bryan Mattison. While Bryan has solely been on the app on the impetus of his friends and thus has not been invested in the online dating process, he is intrigued by Jessie's request in he never having experienced a true family Christmas. Professionally, Bryan was the heir apparent to his now deceased father's property redevelopment business, but hasn't felt yet prepared to be at the helm, leading to his colleague Don temporarily acting as CEO until Bryan decides what to do. While Jessie and Bryan do make a connection with each other, a second more traditional date is affected by whether Jessie is truly ready to move on from Shaun, the events of the day placing pressure on both of them in her family believing he to be her boyfriend and not a first date, and Bryan learning that his company's latest redevelopment project will negatively affect someone in Jessie's family severely.