Tom, a down-and-out bond broker, struggles to keep his business afloat, a legacy of his brother who passed away on 9/11. Claire, a fledgling actress from a small town, starts over in New York after a personal tragedy of her own. As their lives cross, Tom must face the decision to either let go of his fear of loss and acknowledge deeper feelings for Claire or retreat to a darker place. Tom's best friend, Simone, has an identity crisis and an appetite for short-term gratification. Mario, Tom's wingman and a wine enthusiast, must contend with trappings that come with being a womanizer. In the urban maze of New York, the four struggle to say goodbye to old ways to find a better tomorrow.