After discovering the truth behind defiance, Fitz is still struggling to figure out whom he can actually trust. Meanwhile Olivia is trying to move on with her life, and she meets a handsome stranger, Jake Weston, who sparks her interest. But when she and Fitz are forced to be in the same room again, real sparks fly and things get heated. Back at Pope & Associates, the team handles a new case, and for the first time they're working with David Rosen instead of against him.

Olivia and the team are hired by an up and coming politician, Peter Caldwell, but this time instead of fixing a scandal, they're playing high-powered matchmaker. Meanwhile, David is trying to leave the past behind him, but when he feels like he's being followed, he finally turns to the team at OPA for help. Back at the White House, Fitz is still struggling with whom to trust and how to handle a delicate hostage situation, and Jake just won't take no for an answer when it comes to dating Olivia.

Olivia finds herself in the middle of a media storm, but this time she's on the opposing side of the oval office when Fitz's pick for Supreme Court Justice is caught in a torrid affair with Liv's new client, high-powered CEO Sarah Stanner. Meanwhile, Olivia and Jake continue their flirtatious relationship, while Huck takes Quinn under his wing and Harrison and Abby try to figure out where they stand with their friendship. Back in the White House, Cyrus and Mellie continue to fight for Fitz's attention, but someone else may already have it.

The team find themselves working for the devil when Hollis Doyle's daughter is kidnapped and held for ransom. Meanwhile, David is still in danger and is forced to seek shelter at Pope & Associates; Olivia and Jake take their flirtatious relationship to the next level even as the President continues to rely on Jake for intel; in the White House, Cyrus will stop at nothing to get back into the President's good graces; and Mellie's claws come out when she tells Fitz he needs to make some changes.