Dr. Phil continues his work with six of the most judgmental guests he's ever had on the show -- Shirley, a man-hater, Dick, a chauvinist, Jason who hates society, Kim who's morally righteous, Erin, an elitist snob and Crystal, a self-proclaimed bitch -- whom he sent to live in The Dr. Phil House. He wakes the housemates up at 5:30 a.m. via a video message informing them that they are headed for a day of adventure on the high seas. During the van ride to the marina, tempers flare over Kim’s behavior. When the housemates learn they will be working as a team to sail a boat, Erin and Kim refuse to step onboard. Will the other four convince them to make the journey? Next, find out the shocking news Crystal receives and why she threatens to leave The House. Then, Dick and Jason have a secret conversation. What does Jason really think about Dick’s chauvinistic attitude? And, two surprise guests drop by to see Erin. The first rocks her world, giving her just the wake-up call she needed, and the second comes bearing an emotional message Erin can’t ignore. Finally, in a group exercise, the housemates reveal their personal challenges.