Almost in her thirties, Sloane Benson (Emma Roberts) finds herself dreading the holiday season, primarily due to the relentless judgment she faces from her family for being single. After experiencing a recent breakup, her mother, Elaine (Frances Fisher), relentlessly attempts to set her up with new suitors, much to Sloane's irritation.
During a Christmas dinner hosted by her family, Sloane's younger brother, York (Jake Manley), gets engaged to Liz (Cynthy Wu), his girlfriend of just three months, leaving Sloane as the only unmarried individual at the gathering. In another part of town, Jackson (Luke Bracey), an Australian golfer, finds himself spending the holidays with a date he has no real interest in. When his date becomes frustrated over the lack of Christmas gifts, which they had mutually decided to forgo, Jackson leaves her in a state of anger.
After the holiday, fate intervenes when Sloane and Jackson cross paths while returning unwanted gifts. Jackson proposes a unique idea: they should become Holidates, only seeing each other for holiday events to escape the burden of clingy partners. After some initial hesitation, Sloane agrees, and they share New Year's Eve together, only to part ways again without further communication.
Valentine's Day brings them together once more, this time with Jackson pretending to be Sloane's boyfriend when they encounter her ex and his glamorous new partner. Their friendship blossoms as they continue to meet during various holidays. However, complications arise when, after a mishap during a July 4 celebration where Jackson loses a finger, he begins to doubt his worthiness as a partner for Sloane. In an effort to push her towards someone “better,” he sets her up on a date, resulting in a heated argument at her brother's wedding where their respective dates get involved with each other.
Their relationship hits another bump at a Halloween party when Sloane unwittingly consumes laxatives, leading to Jackson caring for her until they end up spending the night together. The following morning brings chaos as Sloane’s married sister arrives and mistakenly assumes something inappropriate has happened, prompting Sloane to shove Jackson away, much to his chagrin.
Thanksgiving sees tensions rise once again when Jackson shares his feelings with Sloane. Their back-and-forth culminates in Sloane's comment about Ryan Gosling while shopping, leading to an argument that ends with them breaking off contact.
As Christmas approaches, Sloane visits Jackson but falters when it comes to expressing her feelings. A serendipitous meetup at the mall presents her with one last chance, and amid a crowd, she boldly confesses her love for him. Their emotional reunion finalizes in a heartfelt embrace.
In the end credits, we see that all couples remain together. Not only are Sloane and Jackson off to Australia for the holidays, but Aunt Susan (Kristin Chenoweth) is officially engaged to Faarooq (Manish Dayal), while Wally (Alex Moffat) and Sloane's mother are dating, alongside Neil (Andrew Bachelor) and Carly’s Mom (Meeghan Holaway). The story wraps with a sense of connection and love, showing that the holidays indeed bring people closer.
