Goodbye to Issa, Molly and the Complex Friendship Love Story at the Heart of ‘Insecure’

·5-min read

SPOILER ALERT: This column includes spoilers from “Everything Gonna Be, Okay?”, the series finale of HBO’s “Insecure.” Read Rae’s breakdown of the episode here.

The cliffhanger going into the series finale of “Insecure” was only a cliffhanger if you hadn’t been paying attention. As ever, Issa (Issa Rae) had to choose between two men: her longtime love Lawrence (Jay Ellis) and, well, someone else (this time, Kendrick Sampson’s Nathan). As charming as Nathan is, and as right as he and Issa can be together, he was always doomed. Ending “Insecure” without Issa and Lawrence ending up together would’ve been a huge curveball — one the show could pull off, sure, but all signs have pointed to Issa and Lawrence going down this road together since the show’s 2016 debut. No matter how many complications “Insecure” kept throwing at them, it was obvious that Issa and Lawrence would be together once they got out of their own way.

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And lo, after the series finale fast forward through birthdays, milestones, and enough missed calls between them to keep them yearning just a little bit longer, they finally admitted their feelings in a quiet conversation that felt downright anticlimactic after all this time. Despite this ostensibly enormous decision Issa had to make, this final season of “Insecure” still felt remarkably low-key — probably because the show’s already resolved the show’s most crucial relationship, which isn’t between the most indecisive of lovers, but the best of friends.

Though the Issa and Lawrence saga always formed the romantic backbone of the show, the pairing of Issa and Molly (Yvonne Orji) has always been the most palpable and pressing heartbeat of “Insecure.” Their friendship, born in college and solidified as adults in Los Angeles, thrives on fun, loyalty and champagne toasts. They can crumple under pressure whenever they allow themselves to be truly honest, to catastrophic consequences. Their love isn’t especially patient, but is still overwhelmingly kind, coming through when both of them need it most. By the time “Insecure” was in its fourth (and best) season, Issa and Molly found that their friendship had come off its tracks — not enough to completely derail it, but enough to feel, as both kept putting it with increasingly miserable disbelief, “off.” What once seemed effortless, they complained to everyone except each other until it was almost too late, now felt like a chore.

That wasn’t exactly true, though. Even as the very first episode of “Insecure” sets up the main conflict as being between Issa, a depressed and complacent Lawrence, and the temptation that another man represents, the episode’s most immediately interesting friction is between Issa and Molly. While the episode bears plenty of the typically pilot hallmarks of a show still figuring itself out, their friendship is immediately a deep and complex thing. While Lawrence sits basically catatonic on Issa’s couch and Molly unsuccessfully dates around, Issa and Molly make up the show’s central relationship. They’re each other’s closest confidantes, but disagree on enough fundamentals that they ended up having the pilot’s most explosive and personal fight. Molly can’t stop unloading all her feelings even when it’s supposed to be Issa’s time; Issa drags Molly into a messy night and ignores her advice; and so it goes, from this first episode through most the series to come.

True to best friend life, this particular argument foreshadows all the other ones we’d see between Issa and Molly going forward. It establishes each of their gripes with the other, the specific kind of miscommunication that kept them mad, and the eventual peace offering that (usually) brings them back together. As these fights became more frequent and frustrating throughout the series, though, both Molly and Issa grew tired enough that giving up and moving on felt like a legitimate option. Their estrangement didn’t come as a shock; it almost just felt inevitable. Maybe, as Molly suggests in the fourth season’s penultimate episode (“Lowkey Trying”) as Issa blinks back tears, the people they had become didn’t make sense as a pair anymore. After everything they had been through, this moment made for the show’s most devastating breakup scene, period.

In the fifth and final season, though, the question of whether Molly and Issa would remain friends was immediately answered with a resounding “yeah duh.” As a (rather convenient) time jump slid past any initial awkwardness, their previous dynamic of prickly disagreement vanished almost entirely in favor of genuine maturity and understanding, leaving “Insecure” free to focus elsewhere. Molly, perpetually successful at work and a disaster at romance, threaded both needles by falling in love with her stable coworker. Issa, constantly plagued by indecision, rejected a glitzy sponsorship and doubled down on her community work. With both of them more secure in themselves than they’d ever been before, their friendship followed suit. Even if Issa and Molly’s newfound growth took the show’s most compelling tension with it, watching Rae and Orji relax into a comfortable rhythm after years of agitated back and forth makes for a solid payoff to all their character work. Growing up doesn’t mean figuring everything out, but it does mean figuring out your priorities — and Issa and Molly decided together that their friendship is, in fact, non-negotiable.

The series finale (“Everything Gonna Be, Okay?”) makes for a joyful, fitting end to a relatively gentle, predictable season of “Insecure.” Molly gets married; Issa gets back together with Lawrence; even Kelli (standout Natasha Rothwell) finds love and gets pregnant with a kid she hopes will one day marry the daughter of her best friend Tiffany (Amanda Seales). But even as the episode resolves the show’s remaining romantic threads, its best and most satisfying scenes still belong to Issa and Molly, whose friendship keeps changing but is no longer in any question. It’s Issa and Molly who get the episode’s climactic, tearful “I love you” exchange, and the final scene of the entire series: a casual phone call that conveys the kind of intimacy only people who know each other inside and out can share. No matter which man Issa ended up with, “Insecure” always understood who the true love of her life is, and will be, through it all.

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