‘Insecure’ Season 5: What’s Next for Issa’s Relationships With Lawrence & Molly?

Insecure Issa Rae HBO

As Insecure‘s cocreator Issa Rae and showrunner Prentice Penny discuss the fifth and final season of their South Los Angeles–set comedy, a theme emerges: “What do you do when you’re not dealt the hand you [were expecting]?” Penny says. “How do you define happiness?”

In last year’s finale shocker, buoyant Issa Dee (Rae) learned her boyfriend Lawrence (Jay Ellis) is going to be a dad; his ex-girlfriend Condola (Christina Elmore) is pregnant.

Insecure Issa Rae Season 5

(Credit: HBO)

“I don’t want to give anything away, but I will say we tried to be very truthful to how all three characters would react,” he teases.

The duo also wanted to show what it takes for Issa and saucy Molly (Yvonne Orji) to heal their friendship, and move creative, self-employed Issa’s career in a new direction: up!

“We’ve always seen her struggle,” says Penny. “We wanted to see how Issa handles success.”

Insecure, Season 5 Premiere, Sunday, October 24, 10/9c, HBO