When his long-running hit series comes to an end, Dean finds himself at a crossroads in life and decides to move back to his small home town thinking he has the experience to take over his family’s law firm, where he butts heads with his brother, Stewart.

After the exciting and victorious Krantz case, Sanderson & Yao gets flooded with cases. Dean, in his usual fashion, wants them to pick the next big case. Stewart disagrees, but he realizes that telling Dean he can’t do something only will make him want to do it more. Soo Stewart decides to encourage Dean and the plan backfires. Meanwhile, Dean inspires Debbie to go for a promotion at work using a “big dog” approach, which puts her job in jeopardy

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.

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.

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".