When Jess and Jake meet at a bar after their office Christmas parties, they find they have something in common. They have both been dumped by their exes the week before Christmas, but they have taken a very different approach to their predicament. Jake is ready to move on, while Jess is determined to get her ex, Dylan, back. Still, the two come up with a plan and make a pact - that they will help each other get through all the obligatory holiday parties without looking alone or pitiful. All goes well except for one thing. Jake is falling for Jess, the exact situation they swore to avoid. When they are stranded by a snowstorm on New Year's Eve and forced to spend the night together, Jake decides Jess is the woman for him. Although Jess says she can't return his feelings, fate seems to intervene when a lost dog finds its way to Jake's door and he and Jess decide to care for him together. Jake is sure that this will bring them together as they shop for supplies, walk, and feed the animal. Jakes begins to feel so sure about things, he buys a ring and decides to propose. But the day he has determined to give her the ring, Jess finds Dylan at her door, begging to come back. Jess tells Jake, and when she goes to see him at his house, he is gone. He cannot allow his heart to be broken once again. Jess realizes she has made a terrible mistake but fears it is too late. Will these two ever realize their love for each other at the same time?