Convinced that the only explanation for Claire’s non-interest in him is that she’s a mole, Dean tells Stewart that Claire is sharing secrets with a rival firm. Although Stewart dismisses the accusation, Dean is set on proving his brother wrong. Meanwhile, Deb and Claire strike up a friendship, the gossipy nature of which propels Stewart to question whether Claire can be trusted after all.

Just as Dean prepares to give up on what he thinks is a hopeless search for love, he is reunited with Gail, an old flame who restores his belief in romance. Meanwhile, Deb encourages Stewart to change his strict ways and let Lizzie have a supervised date with Joel Zadak.

When Ethan chooses to audition for the school play instead of following in his father's footsteps by joining the tech crew, it highlights the differences between those who seem destined for the spotlight and those who live their lives in the shadows. Meanwhile, Stewart confronts Dean Sr. about how he gave his two sons very different life advice.

Stewart convinces Dean he can’t keep using his celebrity if he really wants to be a “regular guy.” But when the brothers find themselves in serious trouble, Dean’s fame might be the only way to bail them out. Meanwhile, Debbie gets an assistant, and ends up being more of an assistant to her.

After spending several holidays away from the family, Dean is thrilled to be reunited with them for his first real Thanksgiving celebration in a long time. But his overexcitement and meddling brings a major, unexpected family secret to light. Meanwhile, a series of flashbacks reveal the chain of events that led to Dean's departure from his hit TV drama.

“The Grinder: New Orleans” -- a spinoff of the original hit series, asks Dean to film a scene giving closure to his beloved character, Mitch Grinder. Not surprisingly, Dean struggles with being replaced by his TV brother, Rake. Meanwhile Stewart, who has also been feeling replaced by his brother in Ethan's eyes, jumps at the opportunity to get Dean back into acting and out of his hair.

After Dean catches Timothy Olyphant making out with Claire, he thinks he can "win her back" by taking the lead on a case - and using very questionable tactics - representing a friend of hers. Meanwhile, Stewart is excited that a reporter is writing a story on him, but becomes upset when Dean steals the spotlight.

Stewart and Deb tell Dean it's time for him to find his own place. Meanwhile, a rival law firm attempts to poach Dean from Sanderson & Yao. Also, Deb becomes reliant on Andre, Dean's former stand-in, who's crashing with the family

After their fallout, Dean and Stewart find themselves on opposing sides during a divorce case. Meanwhile, back at home, Ethan and Lizzie are seeing the impact of life without Uncle Dean, and Stewart and Debbie quickly take notice.

Timothy Olyphant is back in Boise and the rivalry between Dean and him continues when Stewart invites Olyphant to spend more time around Sanderson & Yao. After getting into an argument about who is closer to being a real lawyer, the two "Grinders" decide to go head-to-head in a mock trial.

When Dean scares off a big prospective client by being too dramatic, Stewart tells him maybe it’s finally time to let go of his “Grinder” persona and come down to earth. He tries to convince Dean he should go to therapy. Dean reluctantly agrees, but in typical Dean fashion, he overcorrects and begins “therapizing” the whole family, including Debbie, who is now tempted to quit her grueling job.

Dean's therapist, Jillian, encourages him to, once and for all, shed his Grinder persona and find out who the real Dean is. Through his therapy exercises, he ends up making others around him evaluate their own issues, much to Stewart's frustration.

Stewart becomes certain there's a larger conspiracy against the firm. It’s the first time Sanderson & Yao has ever been involved in a truly dramatic situation, but Dean has shed his “Grinder” persona and refuses to listen to Stewart’s “paranoia.” Instead, Dean decides to focus on being the office intern, so Stew has to take matters into his own hands.

As the conspiracy surrounding Sanderson & Yao reaches a boiling point, the only man who can get to the bottom of it has abandoned the "grind" and enrolled in law school. Stewart, desperate for Dean's help, will go to any lengths to turn his brother back into "The Grinder".

Post-therapy, Dean finds that he has lost the ability to grind. To get it back, he decides to crack the case of the office being ransacked. Meanwhile, in flashback, we see a younger, struggling Dean Sanderson as he must decide whether to embrace a simple life, or pursue his destiny and become the Grinder he was always meant to be.

Stewart is concerned about Dean Sr.'s anger issues complicating their case, so Dean arranges some focus-group testing to see what the masses really think.

Dean and Stewart receive a surprise visit from their mother. Stewart attempts to get reservations to a hot restaurant for his and Deb's anniversary dinner.

When Stew learns that his father is guilty, he wants to settle, but Dean tries one of his old "Grinder" tricks to solve the case. Meanwhile, Stew is concerned that he is now "infected" by "The Grinder".

Stewart becomes sidelined at Dean Sr.'s malpractice trial, causing the rest of the Sanderson & Yao team to try and save the firm.