Vanessa Colway is an uptown girl. Way uptown, Inwood. The kind of place where everyone knows everyone and a murderous tough guy like Jack Driscoll can run his violent protection racket for years without ever setting foot into lockup. Vanessa works hard and tries help her romantic daydreamer of a father run his bar, but she's starting to feel like something has to give.
David Kellen is a master of the universe, a self-styled hedge-fund mega success who has everything he could ever want. But heavy is the head that wears the Wall Street crown, as David has felt his number two, Aston Skinner, nipping at his heels for a long time. His social life is also on ice, which is why he turned to the Swan Club, a top tier matchmaking service for the elite men and women of Manhattan that has only left David, and many of his dates, unsatisfied.
So when David is found on the street, shot dead after another tepid blind date, Goren and Eames assume it to be a crime of jealousy, either personal or professional. However, as the case leads them to Vanessa Colway, the detectives start to wonder how the lives of the downtown titan and the uptown girl ever crossed, and how the dreams of two people simply wanting a normal life could end in murder.