On the 12th Date of Christmas

The film opens with Jennifer Holloway, a meticulous and talented game creator from Iowa living in Chicago, preparing cookies for her boss, Tony, to thank him for a recommendation for the Head Game Creator position. Simultaneously, Aidan Walsh, a cynical but skilled colleague, is helping his sister Shannon and niece Emma with their crumbling family home. The plot kicks off when Tony suddenly quits, leaving the firm's owner, Alastair, in a lurch with a massive client: Wanda from the Devonshire Hotel. Alastair pairs Jennifer and Aidan together to create a Christmas-themed scavenger hunt by Saturday. Jennifer pitches 'The 12 Dates of Christmas,' a concept where each clue corresponds to a line from the song and leads to a romantic Chicago location. Aidan, who prefers working alone, is initially dismissive of Jennifer's 'outsider' perspective, but they begin scouting locations together. They visit Chinatown for 'two turtle doves' (based on a historical turtle race), a cidery in Lincoln Square for 'partridge in a pear tree,' and a French restaurant for 'three French hens,' where they bake a Buche de Noel together. Along the way, subplots emerge: Aidan is desperate for the Head Game Creator promotion to fund repairs for his grandfather's historic house so his father can retire there, while Jennifer struggles with her family's pressure to return to Iowa. After Jennifer takes Wanda's advice to 'speak up,' she formally asks Alastair for the promotion. The tension peaks when Alastair meets with Aidan privately, leading Jennifer to believe she lost the job. However, the scavenger hunt is a massive success, featuring a drum line for the '12 drummers drumming' finale. At the gala, Alastair reveals he has promoted Jennifer to Head Game Creator and Aidan to a new executive role, 'Wizard of Operations,' which provides the salary he needs for his family home. The film concludes with Aidan leading Jennifer to the hotel roof for a surprise '13th date,' where they confess their feelings and kiss.