Issa Rae’s Insecure has been one of the most accurate depictions of the Black millennial experience since its debut in 2016. From its portrayals of work, love, and family, the HBO show is almost too real — who gave Rae permission to spy on me like this? Its fourth season chronicled the all-too-relevant demise of the long-standing relationship between Issa (Rae) and Molly (Yvonne Orji), with each episode spelling out exactly how the ties between the former best friends came undone.
Season four began with a flash forward of Issa telling someone (who we later discovered to be her ex-boyfriend Lawrence, played by Jay Ellis) that she wasn’t really rocking with Molly like that anymore. We were shocked by the revelation, but we quickly discovered that the friendship between Issa and Molly was at its most unstable. While our plucky protagonist poured her energy into planning her first community event, she was unconsciously neglecting her relationships; Tiffany (Amanda Seales) had finally given birth, Kelli (Natasha Rothwell) was still being Kelli, and Molly was tentatively trying to make progress with her new boyfriend Andrew (Alexander Hodge).
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As Issa and Molly continued living separate lives, the distance between them grew wider and wider, leaving space for misunderstandings and passive aggression. It didn't take long before the relationship hit its boiling point, and the showdown unfortunately took place at the last place that Issa wanted it to happen: her block party.
"Nobody has more drama than you, Issa," spat Molly in front of their friends. "You need to figure out your shit and stop using people."
"You are so miserable," Issa countered. "I've been stopped fucking with you!"
Several episodes (and no apologies!) later, Issa meets her former friend in their favorite Ethiopian restaurant, the sounds of Tyler the Creator's "Are We Still Friends?" playing over the somber reunion. Let Insecure's writers tell it, Issa and Molly are endgame, and we're supposed to just accept that.
"We wanted Issa and Molly to learn these friendships don’t grow on trees and don’t take it for granted," showrunner Prentice Penny tweeted after the finale. "We wanted them to be humbled and be appreciative."
"[Issa and Molly] need each other," Penny continued. "That’s the love story in the show. Their life without each other isn’t as good. They need each other."
We wanted Issa and Molly to learn these friendships don’t grow on trees and don’t take it for granted. We wanted them to be humbled and be appreciative. #InsecureHBO
— Prentice Penny (@The_A_Prentice) June 15, 2020
We wanted to get Molly and Issa back together. They need each other. That’s the love story in the show. Their life without each other isn’t as good. They need each other. #InsecureHBO
— Prentice Penny (@The_A_Prentice) June 15, 2020
Call me a cynic, but I'm going to go ahead and call BS. These two haven't been right from the start, and the older that they get, the more obvious it is that they're not a good fit friendship-wise, especially at this point in their lives. At her core, Molly genuinely believes that she's better than Issa; she's judged her on everything from her career to her love life to even her choice in clothes. And Issa does have a demonstrable issue with respecting boundaries — let us not forget the broken pussy debacle that played out in the show's very first episode. Their relationship has been fraught and low-key toxic from the beginning, but it's taken time and distance to see that clearly.
We saw the demise of their connection coming from a mile away. All season, Issa and Molly had been stewing in their respective issues with each other, every passive aggressive comment or pointed look adding to their mile long list of grievances. And the words spoken at the block party weren't just said out of anger — that was how they truly felt. For the first time, it was made very clear that these two had fundamentally disparate ideas of what it meant to be a friend, and that difference really couldn't be reconciled.
It's not that we'd never watched friends fight before, but something about this beef feels like it can't be undone. Even if the writers think differently, Issa and Molly's friendship will be a hard sell in the future. We've seen too much go down to expect this to pan out well.