Bob breaks down a 7-year marriage in which he never told his ex-wife he loves her. Sherwin continues to break the brick incident and callers weigh in on whether they should or shouldn't help in a situation like this.

Sherwin introduces a trivia game he posted on his Facebook page for listeners. Do you think you can answer all the questions. He also discusses how we might already be receiving reparations.

Sherwin discusses dating a subordinate or a coworker. He shares his own experience in this and what he has witnessed over the years. This all comes on the heels of Governor Tony Evers' Chief of Staff who was found to be dating a subordinate but neither he nor the governor stated they care.

Ms. Shack recounts her birthday shenanigans, which include a wild night at JD the Poet's poetry night, a gas station with naked women and going to the strip club with her son. Again, happy birthday Ms. Shack

Mitch McConnell was once again struck frozen while speaking at a press conference. Sherwin dissects growing old when it comes to politics and when is the right time to retire. He also reminisces about his late grandmother and when it is right to intervene and the start of the process of dying.

Sherwin continues his conversation about age and elders. He also receives a very passionate and probably personal call from Al regarding his taking care of your elders who are passing on. Also, happy early birthday to Ms. Linda Shack!

XL Property and Contracting owner Al Cole stops in to talk Sherwin about property management, roof inspections, and his services. He also addresses the recent passing of the 11-year-old who was put in critical condition while bike riding in the hit and run. He talks about what it's like to bike ride in Milwaukee and going to the gym.

Sherwin discusses incarceration rates and stats and how they impact the black community. He dissects racial divides in our society and how racism and unwanted black children are more susceptible to being incarcerated.

Sherwin breaks down intersectionality of the various forms of oppression black people can face. Sherwin also addresses the housing issue in Milwaukee. And Sherwin tries to buy Dave Chappelle tickets on the air but forgets his password.

How clingy is too clingy? Sherwin talks about some dos and don'ts for men when it comes to building a relationship with a woman. He also tackles navigating dating women with children.