As the days pass by, Jack and Jill become increasingly frustrated with their dating experiences. Jack goes out with a woman who talks non-stop, while Jill is set up with a man who only talks about his cats. On Christmas Eve, they both end up at the same ice skating rink, but miss each other by moments.
As New Year's Eve approaches, Jack and Jill begin to lose hope that they will ever find true love. They each confide in their friends about their struggles, and their friends encourage them to keep trying.
On the evening of New Year's Eve, Jack and Jill both end up at the same crowded party. They end up bumping into each other, and as they start talking, they realize that they have more in common than they ever could have imagined.
As the clock strikes midnight, Jack and Jill share a kiss and realize that they are truly meant to be together. They dance the night away, and the movie ends with them walking off into the night holding hands, happy and in love.