Jessica says she believed that once she married her Prince Charming, Jerry, she would never have to work as an escort again. Well, flash forward 27 years later, and Jessica is still keeping men company for money! Her husband, Jerry, says he is just fine with Jessica's profession, but claims that he and Jessica are on the verge of divorce because Jessica doesn't trust him and thinks he's cheating on her! Jessica claims her husband is a lying, uncaring, unsympathetic psychopath, as she has been abused multiple times by her clients. Can Dr. Phil help save this atypical marriage?

Dr. Phil investigates a controversial new law known as "bail reform," where judges will no longer have the power to set bail for a long list of misdemeanors and nonviolent felonies. Dr. Phil meets two esteemed judges, Rosemarie Aquilina and Darrell Jordan, who are in strong opposition to each other on this issue. Then, hear from Akeem Browder, whose brother Kalief took his own life after spending three years in a violent jail for a crime he did not commit because he could not afford bail, and a woman whose nephew died in a car accident caused by a drunk driver who was released from jail weeks after his arrest. Plus, Duane Chapman, aka "Dog The Bounty Hunter," who strongly opposes the new law claiming it favors criminals over the safety of the general public, will join the conversation. How will bail reform affect the average citizen?