Tess and her opinionated older sister Lauren are spending the week after Christmas at the snowy Evergreen Lodge in Vermont and they aren't happy about it. Their stern grandmother, who owns the holiday resort, is not known for her warmth and good humor. But when shy, straight-laced Tess meets Christopher in the lobby, things are suddenly looking up. And when she decides to get out of her comfort zone and create a bucket list of things to accomplish before the New Year-like singing in public and skiing a black-diamond slope-Christopher is happy to help, even as he keeps a secret that could turn everything upside down. When the ball drops, will Tess and Christopher share a magical kiss-or will Tess start the new year off alone?