Issa Rae
Appropriately enough, in the Introduction, the author introduces herself by her birth name, Jo-Issa Rae Diop. This memoir-slash-guidebook is the story of her unlikely rise to becoming a YouTube star of a web series viewed by a million people to the successful film and HBO series creator she is today. It is sort of the story behind the story before the story as it reaches back into her childhood to describe how she became the woman who carved out the most seemingly impossible of scenarios taking her to fame.
redbeard19
Issa Rae beginning her climb to greater fame by manipulating the seemingly limited possibilities of YouTube is a story that traces her awareness of the social engagement of the internet all the way back to the days when America Online ruled the roost. Her first online relationship with a person using the screen name redbeard19. She was just twelve years old and he was nineteen. Already by that tender age she was experience enough in online predatory males to have learned exactly how to answer the question that always—inevitably—came up: “what are you wearing?”
Grandfather
At one point, the author distills the entirety of her grandfather’s being to four significant and well-known aspects: a New Orleans accent, wearing bow ties, laid back charm and a penchant for a melodramatic display of temper. He is also judgmental, harboring a deep and profound dislike and distrust of rap music. One of the cruelest moments in the book is when his temper bullies his charm into complete submission and he blames fast food as the reason that she is “gettin’ to be so FAT.”
Dad
A major turning point in the author’s life occurs within the span of just four seconds when she shows up at her father’s place following the breakdown of her parents’ marriage. Nothing is said, but a kind of panicky “Oh my God” by a woman she doesn’t recognize, but in the course that blink of an eye and ambiguous expression her entire relationship with father threatens to crumble into a memory over the revelations of the past of the “other woman” and the stubborn quality of the present condition of her place in the familial chain.
Louis
A cousin calls up asking for permission to give Issa’s phone number to a guy name Louis. He turns out to have the body of a football player with the mixed African and Asian features known as Blasian. After an initial phone call lingering on for five solid hours, she decided he is the one meant for her. They would marry in July 2021.