The first that came to mind was Jesse and Celine -- our beloved Before Sunrise and Before Sunset characters. After Richard Linklater created a billowing, world-wide sigh with the ending of the second film, audiences have been itching to find out what happens next, so why not a thoughtful piece that takes place over the course of the holidays? It wouldn't work to add a million people into the mix, but I'm sure the pair would find a lot to say about Christmas, and maybe we could finally see how the pair survive in the real (albeit Santa-laced) world.
Beyond the realm of indie romance, can you imagine a certain Miles and Jack taking a New Years Eve trip back to wine country? Pineapple Express getting hidden in a Christmas gift? The Wonder Boys going on a new snow-filled adventure?
Are there any characters you would love to see in the holiday setting? Are any just perfect for dealing with a Winter Wonderland?