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

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.

When a new couple, Lyle and Vanessa Gerhart, comes into their life, Stewart and Deb deal with "The Dean Effect" - people liking you only because you have a famous brother. Meanwhile, Dean finds himself in a similar situation with Claire, the first person he's ever met who isn't affected by his celebrity

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.