When Tom is dumped by his fiancee, friends Cal and Bruce force him back into the dating pool at Mix, a high-end bar in Manhattan's meat-packing district. Out on the town for the first time in a decade, his first encounter -- with a beautiful but brutal attorney -- ends in tears, and things get worse from there. Other members of Union's chic crowd include an engaged-for-now woman, an aggressive single mom, a bubbly waitress, a mysterious bartender, and a failed entrepreneur, who is having the worst night of his life.