The movie: Elf (2003)
The player(s): Will Ferrell and Zooey Deschanel

In order to fully embrace Jon Favreau's Elf with all its charms, you must believe that an attractive young department store employee (Deschanel) would agree to a date with Buddy (Ferrell), a seemingly insane Christmas enthusiast who claims to be an elf from the North Pole. And this is after he busts into the bathroom where she's showering to turn a Christmas carol into a duet. At least he introduces her to the world's best cup of coffee.