Jenee Desmond Harris, Slate’s “Dear Prudence” columnist and podcast host, joins Damon for a discussion rooted in divorce and giving relationship advice during a time when it feels like couples from all walks of life are splitting up. Then, Panama Jackson returns to help Damon advise a young man with cash flow issues who wants to know if he should pursue dating while broke. 

Deesha Philyaw, author of "The Secret Life of Church Ladies," joins Damon for a discussion about making money on the heels of Deesha's two-book seven-figure deal. Morgan the Producer then makes her Dear Damon debut talking tipping etiquette. 

Mitch Jackson, Pulitzer Prize winning author of "Fly: the Big Book of Basketball Fashion," joins Damon to discuss the impact of the NBA on the black community's fashion decisions. He and Damon also share bumps in the road in their own respective fashion journeys.