Reese and Finch must protect Sabrina and Daniel Drake, a married couple who own a very successful publishing firm. Initially, it appears that the Drakes are the target of an Appalachian militia group who were angry over a book their company published, but it's quickly revealed that the Drakes have taken out a hit on each other. Sabrina contracted a professional hitman by the name of Cyril to off her husband, while Daniel paid off a junkie and former friend to kill his wife. Reese tries to stay one step ahead of the couple's hired assassins, eventually taking both Sabrina and Daniel hostage to keep them safe and talk out their marital issues. Unfortunately, even when Sabrina and Daniel decide to call off the hits and try to reconcile, their hired killers won't take no for an answer. Using the Drakes as bait, Reese lures the hitmen to a Finchian safehouse and takes them down with the help of Carter and Fusco.
Meanwhile, Carter and Fusco make slow progress in their own romantic arenas. During the course of the investigation into the Drakes' assassins, Carter meets Detective Cal Beecher, a handsome narcotics detective, and she eventually agrees to go out for dinner with him. Fusco is forced to take his date, a Jersey girl by the name of Rhonda, out on a stakeout at Finch's request. They end up bonding over his job and enjoying falafel.
In a flashback, we see the early beginnings of Finch's relationship with Grace, the woman he was forced to leave to keep the machine safe. He plans an intricate scavenger hunt, which ends with a beautiful private dinner at the Guggenheim, where Finch shows her Chirico's "The Red Tower," which he anonymously bought and donated for her.