The first time we met Issa Dee in the Insecure pilot, she was turning 29, and felt stuck in a relationship with longtime boyfriend Lawrence (Jay Ellis.) When the stylish HBO sitcom returns on August 12 for season 3, Issa (played by co-creator Issa Rae) is phasing into her 30s. Professionally, she’s hitting a wall: Reduced to a desk job at edu-charity We Got Y’All, part-timing in the gig economy as a Lyft driver. Her romantic life is worse than messy. It’s boring. Ex-boyfriend Lawrence is nowhere in sight. She’s couch-crashing with Daniel (Y’Lan Noel), her own personal It’s Complicated, who spends nights having loud sex while she tries to sleep in the living room. She’s struggling in every direction. You could say that [pushes glasses up nose] she lacks security.
It’s a low point for Issa. But the first four episodes of Insecure‘s third season are all highs, sending the characters in new directions. Previously, Daniel was a tantalizing temptation. Now he’s a three-dimensional character, and I love how Noel shades his pursuit of rap-game success with nerdish sensitivity. (Forget those played-out bass beats, Daniel’s all about the strings!)
The second episode follows Issa and Daniel to a night out at a club, a perfect venue for their unique will-they/won’t-they/what-they dynamic. And no show on TV does “going out” as well as Insecure: The embarrassing chitchat, the struggle to look like you’re not struggling to look cool, the seductive possibilities of drinking (responsibly) and dancing (irresponsibly). The fourth episode is a different kind of semi-date scenario. On a long sunny lunch break, Issa takes a dream-eyed new love interest on a local-hotspot tour. There’s her favorite bookstore in Leimert Park. There’s that great BBQ joint frequented by the mom from Family Matters. The sweet flirty banter merges seamlessly with a romantic vision of South LA splendor.
As a performer, Rae has a tangible comedic awkwardness that masks a deep well of self-confidence. She’s perfectly matched by Yvonne Orji, who plays Issa’s best friend Molly with brash assurance that can’t hide a burgeoning confusion. Molly’s starting a new job at an all-black law firm, a utopian-seeming office with its own brand of workplace politics. She’s still seeing Dro (Sarunas J. Jackson), Mr. Open Marriage, so that’s another It’s Complicated.
Insecure juggles these complications marvelously, blending swoony-sexy swagger with laugh-out-loud comedy. The four episodes I’ve seen push the central characters to moments of change, some minor, some life-altering. And then I love when Molly and Issa get to just hang out, going Full Squad with Tiffany (Amanda Seales) and Kelli (Natasha Rothwell, so hilarious she’s heroic). There’s a big plot tease in the first half of this season. The four women are planning to attend a certain desert music festival beloved by the worst people on Instagram. Holy Millennial Hell, can Insecure survive Coachella? I can’t watch. I must watch. A