In a nutshell: Issa’s feelings about her sister are still all over the place.
Who’s the villain: Issa’s nemesis, Barry Williams, aka the founder of Phony Babies, was introduced in the Season 4 finale and is returning with plenty of drama on “Insecure.”
What we learned: Barry is best friends with Issa’s divorce lawyer/girlfriend (and Barry is coming for Issa!), Anika. However, Anika is all kinds of mad because Barry decided to turn over the majority of his Phony Babies to charity. “Honestly, no matter how much money you say you have, it doesn’t matter to me. You didn’t have a dime when you came,” she tells Barry. He even offers her $15,000. “This is not a Zeta Phi Beta thing,” he says. “I don’t have anything to offer you in return. And this is not about money.” Anika promptly denies. “You don’t know that. You don’t have to feel that way about people like me. None of us in this group do. It’s not a betrayal. It’s not keeping secrets from people. We’re just trying to survive right now,” she says.
Issa and Barry have been having issues with each other for a while, and Issa’s feelings about her sister are still all over the place. She’s clearly conflicted over her relationships with both her sister and Barry and which direction she should go in moving forward with her life.
“This is our childhood,” she says. “This is our family. It’s not going to work out and it’s not going to be easy. You don’t have to do this. You don’t have to talk to me. You don’t have to love me. We’re on the same side. We’re not dumb. We’re not stupid.” But she tries to soften things up with Barry with a rose bouquet. “Just remember,” she says. “You’re not different. You’re not a monster.” She pulls out a notebook and is reading a poem her sister wrote about their childhood, which Barry listened to on his headphones. Issa is definitely trying to give Barry a little hope.