Critic’s Notebook: Saying Goodbye to ‘Insecure’ and Its True Love Story

The series finale of Insecure, which airs Sunday on HBO, will conclude one of television’s most charming, frustrating and at times disappointing love stories. I’m, of course, talking about the relationship between Issa Dee and Molly Carter, whose feuds and reconciliations, side-eyes and giggles anchored Issa Rae’s masterful show about contemporary Black adulthood.

When Insecure premiered in October 2016, America was inching toward electing an authoritarian president and coming down from the euphoria of a Black man’s ascension to the land’s highest office. “Black Girl Magic,” a hashtag coined by CaShawn Thompson, had blossomed into a movement, but television shows focused on Black women were still few and far between. Insecure, inspired by Rae’s phenomenal web series The Misadventures of Awkward Black Girl, felt like a welcome escape and a breath of fresh air.

The show wasn’t radical — as Doreen St. Félix astutely notes in a recent review, Insecure is indebted to Black sitcoms like Girlfriends — but it was exciting. Over the last five years, Rae, along with director Melina Matsoukas, showrunner Prentice Penny and cinematographer Ava Berkofsky, has constructed an inviting world textured by a chic visual style and an expert use of Los Angeles locales. Digestible plotlines, topical witticisms and Issa and Molly’s string of sexy romances were enough to guarantee Insecure’s prominence within a certain Black cultural milieu.

But it was the relationship between Issa (played by Rae), a nonprofit employee who felt trapped by her job and relationship, and Molly (Yvonne Orji), an ambitious and self-sabotaging corporate lawyer, that kept me tuning in week after week. Their friendship possessed an easy energy and warm familiarity. They randomly called each other to gossip and vent, honored rituals in the form of date nights and spoke their own language (“Malibu” was a word they frequently invoked when they wanted to confess a blunt, potentially painful truth). In a culture starved of considered portraits of Black friendship, Issa and Molly’s platonic love story offered a nonjudgmental map of two people trying (and sometimes failing) to see and be seen by each other.

The early episodes of the first season acquainted us with the rhythm of their imperfect bond, revealing the faint cracks that would eventually become fissures. Although the two relied on one another, they had fallen into an unsustainable pattern: Molly often came to Issa to lament or complain about her romantic troubles, and Issa would dutifully listen and occasionally offer a meek reality check. At the end of the series premiere, when Issa raps about an inside joke they shared earlier, Molly feels betrayed and belittled. “That’s the problem, Issa, you don’t stop to think about the shit you do,” she yells. The accusation prompts Issa to bitterly protest that she is always listening to Molly. Later, when Issa suggests Molly might benefit from therapy, the latter feels offended, and it culminates in a heated exchange that leads the two to briefly stop speaking.

Although Issa and Molly always managed to kiss and make up, communication issues plagued them, eventually pulling the duo apart. Insecure’s gift was its ability to rigorously capture the nuances of these failures — to show how Issa and Molly let problems fester and took each other for granted. Season 2 featured their relationship at its strongest, when Issa, in the wake of her break up with Lawrence (Jay Ellis), leans on Molly for support. The pair gossip about Lawrence’s alleged new lover and scheme to get more information. Molly fakes a run-in with Lawrence at his new job to try and get him to forgive Issa. By the end of the season, when Issa realizes that her relationship is really over, it’s Molly who plans an elaborate Moroccan-theme date night to cheer her up.

By the third season, however, life changes (or the lack thereof) began to wear the women’s relationship down. Molly assumes a chastising maternal role, frequently berating Issa for her life choices. She stops listening to her friend, and the impact of that becomes clear in the season finale, when Molly dismisses Issa’s idea for a career pivot and confesses that she turned her friend’s new love interest, Nathan (Kendrick Sampson), away on her behalf. “I know you were trying to help,” Issa scolds, “but b***h, I’m not you.”

The implications of that statement governed Insecure’s confident fourth season, in which the show leveled up both its aesthetics and its character development. Issa and Molly, now in their 30s, were growing up, and growing apart. Not listening, making assumptions and choosing to ignore tensions combined to erode what always felt like a guaranteed intimacy. Their friendship devolved into one big missed connection, their attempts at confrontation or even low-stakes conversation feeling ill-timed and inconvenient. Issa, who in some ways had less of her life figured out than Molly, embarked on new career ventures. Starting her own business consumed her, making her less available to her friend.

At times, this study of a relationship unraveling made for a sluggish season, but I didn’t mind. Issa and Molly saying the wrong things, crossing boundaries and struggling to apologize or extend grace seemed like a natural development. The season acquired the gravity of a romance in which two lovers repeatedly ambush their own relationship.

But Insecure wasn’t always just about Issa and Molly. Hovering near and around the duo were auxiliary portraits of camaraderie. Tiffany (Amanda Seales) and Kelli (Natasha Rothwell), close confidantes outside of the quartet, served as both comic relief and reminders of alternative ways of navigating companionship. Kelli and Tiffany initially seemed, at least to me, incompatible, the former comical and liberated and the latter stiff-lipped and bougie. But they gelled more smoothly than Issa and Molly because they prioritized, above all else, being there for each other. “When you and Tiff had your issues,” Molly asks Kelli during the fifth season’s premiere, “how long did it take for you guys to get back-back?” “Just keep being there for her,” Kelli suggests. “Like, what does she need right now?”

I came to Insecure already a fan of Rae. I had stumbled upon Awkward Black Girl in high school, and religiously tuned in when new episodes dropped. I would then dissect each one — they were never more than 10 minutes long — with two friends on our Facebook walls. (We have since, thankfully, moved to a regular group chat dedicated to the same exercise for Insecure). Awkward Black Girl comforted me by dramatizing experiences and feelings I found familiar.

Insecure provided that too, but for friendships. Molly and Issa were temperamental, dramatic, prone to saying regretful things to one another and just plain messy. But the show, similarly to ABG, attached no judgement to these less flattering tendencies, choosing to fold them into the plot and illustrate how the growth or regressions in the central relationship impacted other parts of these characters’ lives.

In reflecting on the last five seasons, I couldn’t help thinking about the late scholar bell hooks, who, in All About Love, writes: “friendship is the place in which a great majority of us have our first glimpse of redemptive love and community. Learning to love in friendships empowers us in ways that enable us to bring this love to other interactions with family or with romantic bonds.” Molly and Issa’s relationship not only sustained them; it was the fertile ground on which the two women grew into better versions of themselves.

It was disappointing, then, to watch Season 5 miss an opportunity to portray the disjointed and strenuous nature of reconciliation. After the previous season, Molly and Issa’s friendship hung in a fragile balance. Could they find a way forward? The short answer was yes, of course, but tidying that up with a convenient time jump two episodes in partially betrayed the show’s journey. Why recycle Issa’s stale romances with the same underwhelming men instead of delving into the relationship that kept her afloat? Wouldn’t it have been far more satisfying to see how Issa and Molly arrived at recommitting to their relationship?

The season did offer glimpses of growth. Molly and Issa’s lives were not any less complicated, but their friendship was different. Sprinkled throughout these new episodes’ dramatic turns were signs of that change: Molly taking Issa’s advice, for example, and neither being so quick to judge the other or assume they know what is right.

These moments grounded this epochal series, which ends with a declaration far more poignant than either Lawrence or Nathan could ever give Issa. “Thank you for everything,” Molly tells her best friend during a teary moment in the finale. “For being you, for loving me while I was me. Girl, I don’t know where life is going to take us, but I just know that as long as you’re around, I’ll be ok.” If that’s not true love, I don’t know what is.

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