In Search of a Midnight Kiss (2007) on Netflix

On New Year's Eve, Wilson, a twenty-nine-year old guy has just had the worst year of his life. He emigrated to Los Angeles, has no date, no concrete plans and every intention of locking the doors and forgetting the last year ever happened. That is until his best friend, Jacob, browbeats him into posting a personal ad on Craig's List. When Vivian, a strong-willed woman hell bent on being with the right guy at the stroke of midnight responds, a chaotic, sometimes hilarious, sometimes touching journey through the black and white streets of L.A. begins. In the waning hours of the year, emotional vulnerability and bitterly honest humor seem to be waiting around every corner.