Rachel Martin, the dynamic host of NPR's Wild Card, invites Issa Rae, the talented actress and creator behind Insecure, for a playful yet profound conversation. They dive into childhood pride moments and how to stay connected with those we've lost. The discussion reveals how simple questions can unlock deep connections and reflections on joy, grief, and the impact of personal memories. Through humor and honesty, they explore the beauty of imperfection in life and creativity, creating an intimate space for sharing life's biggest questions.