As fate would have it, Jennifer and Aidan both work at the same Chicago scavenger hunt company. Yes, a company that plans and executes scavenger hunts on behalf of anyone crazy enough to pay them – typically as corporate team-building things, which is a sad and terrible market around which to build a business. Not only do Jennifer (Mallory Jansen) and Aidan (Tyler Hynes) both work at the same place, they’re vying for the same promotion. Aidan has more experience, but Jennifer has a certain creative spark, which does not go unnoticed by their new client who is relaunching one of the city’s swankiest hotels. This means that these two rivals, one a Christmas fiend, the other a self-described lone wolf, will have to work together on the firm’s biggest project to date.
The theme is the 12 Days of Christmas, but their inspiration leans more toward the romantic – the 12 Dates then. And for some reason instead of just thinking of clues in their heads or brain-storming at the office, they decide the only thing that makes sense is to hit the town and do the dates themselves. Strictly as professionals of course, just a couple of colleagues who realize that incorporating their date selfies into the pitch is a needless but brilliant way to expense wine tasting on company time. Who could have guessed that going on a bunch of romantic dates together could make you fall in love?
Script writers Christine Conradt and Jamie Pachino take the time to set each clue in a unique location of Chicago, all twelve in different historic districts so the scavenger hunters will have the opportunity to enjoy the whole city before eventually being led to the luxury hotel’s grand opening in its ballroom, all decked out for Christmas (where, incidentally, Jennifer and Aidan’s boss also awaits to announce the promotion). Unfortunately, the siren song of tax breaks and nearly year-round snow cried out to director Gary Yates, who filmed the thing in Winnipeg, Manitoba. So if Chicago looks good to you, fly to Canada instead.