revisiting insecure: the complex dynamic of Issa & Molly.

who was wrong?

Rewatching Insecure as an adult is an insanely different experience compared to when I was in my teenage years/early 20s. As a 25-year-old woman who is not only Black, but also a passionate creative– I see Issa Dee’s character and her experiences mirror mine, so much so to the point where it scares me. Transitioning into adulthood (more specifically your mid-20s) is no easy feat. Your frontal lobe is finally developed, you’re somewhat aware of your flaws, you start seriously wondering about your future, and you’re constantly in this state of wondering where you fit in. At 25, I approach friendships and relationships differently, and my realizations about life have become a shocker to me largely because my brain didn’t work this way a year ago. Friendships, in particular, have become important for me and a priority, as community is essential to survival. While we all want to believe that we’ve healed and done the work on ourselves, that can never be truly tested until you are in relation with others.

Insecure does a wonderful job at portraying the complexities of life as an adult. Adulthood doesn’t come with a handbook and all of our journeys are diverse and abstract. You meet different people in your life from separate backgrounds with different communication styles, quirks, flaws, and personalities. You are then tasked with the challenge of learning how to properly navigate friendships and relationships while keeping all of that in mind. It can become difficult. 

What stuck out to me was the friendship dynamic between Molly and Issa. While at first, I hated Molly when I initially watched these episodes, I see that Issa had to do with the demise of their friendship as well. If we’re arguing about who was the shittier friend, it was definitely Molly in my eyes. However, they both contributed to the end of their friendship. 

From my perspective, Issa was always a carefree, open-minded, and fearless woman. Even in spite of her personal insecurities as far as her living situation, finances, and love life– she was so obviously passionate about life and her professional success. She looked at life through an optimistic lens and had this ability to humanize people, even in spite of their fuck-ups. Take the situation with Nathan, for example. We learn later on in the series that he ghosted her because of his bipolar disorder, yet Issa is open to understanding him, showcasing her ability to see the nuances in people’s lives—a trait that both aids and complicates her own existence. Conversely, Molly’s more rigid demeanor often contrasts sharply with Issa’s empathetic and nurturing approach, creating a rift between them, particularly during critical moments. When Nathan shows up to her apartment with intentions to apologize, Molly catches him– urging him to go away, as it was Issa’s birthday. Molly presents as the stoic, stern, and anal one of the two– which explains their disconnect. Eventually, Molly tells Issa that Nathan showed up, to which Issa expresses disappointment that Molly did not tell her.

Throughout the series, Issa relies on Molly for… a lot. Every time Issa finds herself in a sticky situation, the first person she calls is none other than Molly. Her life seems to be the very definition of chaotic, messy, and unhinged. She stayed with her ex, Daniel– as she looked for housing, she cheated on her boyfriend, and she eventually begins to work with Condola– Lawrence’s new girlfriend– during her block party project. She does Lyft for a while to support herself and we always see Molly in the background seemingly supporting her as she navigates these changes. Molly is always the friend that Issa goes to through her trials and tribulations, serving as her savior. 

What I realized while watching, was that Molly actually loved the fact that Issa was a tragedy. Molly seemingly had her life together. A car, a college degree, a condo, a great corporate job, financial stability, and a conservative approach towards life. Compared to Issa, she’s uptight and has an image to uphold– being sure not to let anything get in the way of that. She even idolizes her parents’ marriage, putting them on a pedestal while seeking to model the exact bond that they have. Molly idealizes life and everything is curated for her. She puts up a facade in public, despite her equally messy life behind closed doors. She engages in a casual relationship with Dro– a married man who happens to be in a polyamorous relationship, she entertains Jared– a Rent-A-Car employee– way below Molly’s pay grade, and her love life is in shambles. Even with all of her mess going on, she maneuvers through the show as if Issa is the only one who is constantly in mess and looks at Issa with a judgy disposition that is evident throughout her body language and tone. It was almost as if Molly looked at Issa with this perspective that she was above her. She felt this need to put up a facade that Issa simply never had to do. Issa was open and honest about her shit, yet Molly failed to do the same, even in her interactions with others. There was this incessant need to control everything and to show up as the best curated version of her that could possibly exist. Regardless of all her mess, it becomes clear that Molly subconsciously found joy in the fact that Issa was experiencing turmoil, while she had the luxury of having others believe she had everything together. Molly reveled in being the ‘savior’, and enjoyed the fact that from the outside looking in— her life sounded like a breeze.

If we have to be real, Molly was unapproachable, critical, and draining to be around. She took pride in being stoic and withdrawn. She equally took pride in the fact that she had standards– and while those are great things to have– having them to a point where you are unable to hold empathy for others nor see the error in some of your unrealistic approaches to life– is harmful not only to you, but everyone else who is around you. Molly always had something to say about what Issa was doing with her life– and while holding friends accountable should always be something that is embraced– there is a way to do it tactfully. Her critical approach towards Issa often veers into judgment, manifesting in backhanded remarks and a condescension that is unsettling. This not only weakens their friendship but also poses challenges in Molly's romantic and professional pursuits, as men and coworkers often perceive her as overbearing and annoying. In contrast, Issa’s laid-back yet honest approach to life allows her to navigate her messiness with an authenticity that Molly struggles to replicate. The dynamic between them exemplifies the struggles of adult friendships, where disparate personalities collide and create tension. Molly, while well-intentioned, often loses sight of the importance of empathy and compassion, leading to an unapproachable persona that drains those around her. Issa's natural charm and ingenue appeal stems from her authenticity and her ability to embrace her journey— full of detours and stops. She handles life's challenges with this radical honesty, building genuine connections with others and inviting in opportunities that her friend often seems to miss— both in the workplace and in her romantic life. As a result, Molly finds herself struggling with the realization that her pursuit of perfectionism has not enhanced her desirability, especially when compared to Issa, who, despite her own social awkwardness and instability, remains sociable and engaging. People are intrigued by Issa’s depth, rawness, and unique sense of humor— making her likable.

During Issa’s mixer event at her apartment complex for the Block party she was working on, audiences witness Molly’s passiveness and backhanded compliments regarding Issa in a conversation she has with her new fling, Andrew, before they enter the event. She forewarns him that the event may be a little too “homegrown” and to brace himself for a different demographic, ending the conversation with “she’s trying though”, undermining Issa’s career win. Molly even used Issa’s event to talk about an issue she had with Andrew, obviously annoyed that Issa dismissed it and prioritized her event over her concerns at that moment. Keep in mind, this event was important as it was Issa’s opportunity to pitch to investors and vendors for her block party.

As Issa begins to forge valuable connections and experience professional growth, Molly finds herself feeling sidelined. Her initial resistance to Issa's progress stems from her own insecurities; she struggles to accept that her friend can thrive amidst chaos while she feels compelled to maintain a facade of control and perfection that she clearly is not comfortable with. Molly hasn’t exactly mastered the art of letting go and not being in control of everything— something we see that she slowly is breaking through during her relationship with Andrew. While Issa embraces her flaws and chaotic nature, Molly’s strive for perfection causes her to inadvertently resent Issa’s freedom and unapologeticness, as well as how far it takes her.

For the first time in their friendship, Issa was finding professional success and Molly was finally in a healthy relationship. Both friends were adjusting to their new roles in their personal lives, and while Molly is clearly a control freak and can be a snooze fest to be around– I want to be clear that Issa was no angel either. I just don’t believe she was as horrible to Molly as Molly was to her. From my lens, Issa was flighty and inconsistent. She was also a tad bit self-centered, which can honestly be attributed to the things she was going through in her life– financial instability, housing issues, and unemployment. Though Issa’s choices may be questionable—like the ill-advised "Broken Pussy" anthem—she possesses a trait that Molly lacks: the capacity for accountability. This distinction in character becomes a crucial element in their relationship, as Molly often deflects criticism and resists reflecting on her flaws, choosing instead to maintain her facade of perfection. Issa always apologized and continuously ignored Molly’s passive aggressive digs, while Molly was comfortable being the stern bitch that she was, rather than using the feedback to reflect. This becomes even more obvious in Molly’s therapy sessions. Molly is always right, never wrong— constantly rejecting any valid critique from her therapist.

During their Self Care Sundays, Molly opens up to Issa about Andrew’s emotional unavailability. Issa responds by saying that Molly finds an issue with everything, failing to see the new Molly that is right in front of her. At that moment, Andrew calls Molly and apologizes for being too distant– and after the phone call, Molly tells Issa that it was her job that called her, not feeling comfortable enough to share that it was Andrew. Issa then goes on a tangent about herself and her ending with TSA Bae, making the conversation about her. The camera pans to Molly's face, where we clearly witness a disconnect– as she is no longer in the same space as Issa. 

The lunch scene with Condola was a major fuckup on Issa’s end. Issa invites Molly for lunch after finishing up a conversation with Condola, and when Condola insists that she leaves the two alone to enjoy each other’s company– Issa encourages her to stay, not taking Molly’s feelings into consideration. Once again, Issa is not showing up for Molly at this new point in her life, and we are witnessing a drift in their connection. Molly is rarely able to open up about the relationship, as Issa is still clinging on to old Molly. Issa is now in a new stage where her career is center stage– and rightfully so, after a tumultuous year. However, this focus on her professional journey sometimes comes across as self-centeredness. Regardless of her intentions, Issa’s actions leave Molly feeling isolated and neglected. It’s essential to recognize that while Issa may not be aware of the emotional impact of her behavior, the lack of transparency in Molly’s communication exacerbates the issue. Molly’s tendency to express herself in passive-aggressive ways, instead of being upfront about her feelings, creates a situation where Issa assumes everything is fine. Issa isn’t a mind reader. So, can we really blame Issa for Molly’s inability to express her discomfort towards Issa’s actions? In a loving friendship, your needs will never be met if you fail to voice them. This is where Molly encounters a significant hurdle—her silence creating an issue that ultimately falls on her, not Issa.

Undeniably, however, Molly genuinely cared about their friendship. In the grocery store scene, where Issa points out the fact that things have been weird between the two– they come to an agreement that they would talk about it during Thanksgiving at Molly’s mother’s house. Molly is eager for them to have the conversation, but Issa flakes on Molly, reinforcing this theme of unreliability in their relationship. In every season, Molly has always been there for Issa when she is going through something, yet in this chapter of her life, Issa is failing to reciprocate that same energy. Issa’s flaky behavior suggests that the friendship is not a meaningful prioritization, and even if these are not her intentions, her actions tell a different story. 

Ultimately, what really nailed the end of the friendship was when Issa reached out to Andrew (Molly’s boyfriend) for help with a headliner for her festival, since Schoolboy Q dropped out last minute. Initially, she asked Molly to ask him– to which she declined due to her not wanting to ‘mess up a good thing’ or bring Issa’s problems to a relationship that was exciting and healthy to her. Issa respects her decision and instead asks Nathan (Andrew’s roommate and friend) to ask him. At the festival, Molly finds this out and confronts Issa about it, where Issa explains that she didn’t ignore a boundary by finding an alternate solution that did not involve her. An argument erupts and Molly calls Issa selfish, messy, and a backstabber, with Issa telling Molly that she’s always finding an issue with everything. At this moment, I didn’t understand what Issa did wrong as a viewer. Boundaries were clearly respected and she went about getting what she wanted without involving Molly. She never tried to persuade Molly even after she declined her request. Issa respected it. I found it off-putting that Molly refused to help Issa, however, with a small favor after witnessing Issa struggle for the entire year with homelessness and unemployment. It made me wonder: did Molly really care about protecting the sanctity of her relationship? Or did she hold some resentment towards Issa’s success?

I believe that Molly was used to Issa always relying on her for help, and in this moment since she found an alternative— that was an issue for Molly.

I recently went through a friendship breakup that strikingly mirrored this exact dynamic down to the T. In revisiting the show, it has provided me some comfort and solace in knowing that my experiences are not only exclusive to me. Friendship breakups happen all the time and the show did a phenomenal job at exploring the friendship dynamics of Black women, as well as the different ways that insecurity and miscommunication can manifest into hidden resentment and the outgrowing of a friend. With each episode, I am reminded of the importance of open communication and mutual support.

What can’t be denied, however, is the love that both of these women had towards each other. They fiercely protected one another even if they were beefing. The drift was created because both of these women lacked boundaries, and Molly had trouble speaking up, as well as her own insecurities. Molly felt a pressure to always show up as the ‘strong Black woman’, which makes sense— especially considering the fact that she worked in corporate America and was a Dark skin Black woman. Molly was always on defense and it made her hypercritical, while also making her less enjoyable to be around. Issa was experiencing a period of instability which then translated into her communication and tendency to be unreliable. As the show progresses and both ladies experience a break from one another, they eventually come back— seeing the error in both of their ways and approaching the friendship with a soft, tender approach.