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The Peril of Issa and Molly’s Fractured Insecure Friendship

Issa Rae and Yvonne Orji in Insecure.
Issa and Molly, finally together again. Photo: HBO

There’s very little that’s quite as traumatic as a friendship in decline.

HBO’s Insecure, which concluded its fourth season Sunday night, took great pains to demonstrate just how emotionally damaging it can be when you fall out with your friends. After ten episodes of tense negotiation around the changing nature of their relationship, Issa (Issa Rae) and Molly (Yvonne Orji) ended the season by finally making the time to have the hard conversation they should have had weeks ago. But not before everything else in their lives had imploded first, forcing their ongoing friction into sharp relief.

Issa and Molly’s friendship has always been the linchpin of Insecure. Despite their squabbles and messy, awkward behavior, the show has always been — or at the very least, always tried to be — about the relationship between these two best friends. But everything worth fighting for is hard-won, and this season, the show was brave enough to truly examine their dynamic.

The main plot of Insecure’s fourth season has been Issa and Molly’s largely unspoken conflict. What started as small digs and shady remarks culminated in a full-blown screaming match at the block party that represented a critical moment for Issa’s career. But as bad as the women’s relationship became, it was obvious to everyone outside of it — both viewers at home and any character within their orbit — that all they really needed was to take the time to air their grievances and listen to each other. Instead, they let it fester, slight after slight piled up into a towering heap of hurt and resentment.

One of the obvious issues with Issa and Molly’s relationship was that, essentially, they had both grown. Over the course of the show, they’d each made personal strides that made them more desirable friends and lovers. But change isn’t easy, and it’s hard to acknowledge progress in others when you’re insecure about the changes in your own life.

Their conflict began as an equitable squabble. Issa was unkind about Molly’s budding relationship, and Molly was dismissive of Issa’s new career ambitions. Each of them was comfortable seeing the other in a very specific role they had begun to outgrow. To Issa, Molly was the one with the messy love life who couldn’t figure out a way to settle down long term. To Molly, Issa was the unfocused loser without any solid career ambition. But while those things might have been true for each of them in season one and even in season two, by season four, Molly had found a generous man who wanted to be serious about their time together, and Issa had finally found the thing that she shined at.

When you’ve known someone as long as Molly and Issa have known each other, it’s hard to imagine them as anything other than the way they’ve always existed in your imagination. For both women, their friend’s growth was an affront to the relationship they had established with each other — growing into themselves upset the delicate equilibrium of their relationship. Predictably, they both handled it poorly. Each felt attacked when the other didn’t acknowledge how they had grown and attacked the other in turn. Instead of cheering each other on for working on themselves and making improvements that brought them closer to the people they wanted to be, they quietly resented each other for changing. Without the reliable and established roles of their friendship, they were unmoored.

Brilliantly, Insecure showed how each woman’s myopia affected the relationships they had with other people. For Issa, it meant an insensitive handling of former flame Nathan’s (Kendrick Sampson) mental health issues when he suddenly reappeared in her life. But for Molly, the consequences were far more dire — the dissolution of her most significant romantic relationship to date.

Molly’s arc with Andrew (Alexander Hodge) has been both a joy and a terror to watch. Clearly infatuated with the beautiful hunk of a man that he is, Molly found herself in the relatively new situation of having to incorporate a serious relationship into her working life. Andrew was patient and kind and always on her side, but he spotted Molly’s stubborn streak early. By the back half of the season, he had tired of pushing against it, making their breakup in the finale bitter, but inevitable.

The breakdown of Molly and Andrew’s relationship was a reflection of her issues with Issa. Molly’s primary problem is that she does not bend. Perhaps a function of her law career or maybe just a personality streak, Molly demonstrated over the course of the season that she could not conceive of the possibility that she was at fault. Over and over again, she behaved as though she held the moral high ground and deserved to be treated as such, despite that not being the case. Her inevitable blowup with Issa over securing talent for her community block party didn’t acknowledge that refusing to help a friend in need was a shitty thing to do, regardless of the state of their relationship at the time.

It’s not as though Issa wasn’t also at fault: Asking for a favor without ever addressing the tension that had built between them was foolish at best and brazen at worst. But when Molly refused to help her, she drew a line in the sand that couldn’t be erased with vague platitudes or uncomfortable silences. It was then that their relationship moved from awkwardness to full-on feud.

After the block party, both women were so caught up in their ongoing issues that they missed the warning signs of Tiffany’s (Amanda Seales) postpartum depression. When the finale brought the two back together in search of their missing friend, it was a wake-up call that led them back to the Ethiopian restaurant that grounded their relationship, so they could finally face each other and hash out the unpleasantness that had built up between them.

It was a fitting end to a season that saw each woman try and fail to be happy without the other in their life. Importantly, it was Molly who reached out this time, finally bending and allowing herself to make the first move. After letting things get so bad that their friendship was almost irreparable, they made the choice to try again, knowing that there were no guarantees. With Molly’s breakup and Issa’s shock of learning that Lawrence (Jay Ellis) got Condola (Christina Elmore) pregnant, there’s no way to know what the next step of their relationship will look like. But the important thing is that Insecure allowed itself to examine the fallibility of that friendship and imagine a future in which it no longer existed. Thankfully, from the looks of it, that future won’t be their reality.

The Peril of Issa and Molly’s Fractured Insecure Friendship