In this interview special, Diane talks to Prentice Penny, who ran INSECURE with Issa Rae, his comedy writing credits also include BROOKLYN 99 and HAPPY ENDINGS. Penny talks about the groundbreaking comedy of INSECURE and his thoughts about how comedy is changing as the industry sloooowly has more POC in decision-making positions. The second chat is with journalist Amy Odell, who writes the Back Row newsletter and wrote the wonderful book ANNA, about fashion empress Anna Wintour. Diane and Amy talk about Fashion on TV in INSECURE, AND JUST LIKE THAT and SELLING SUNSET.