On ‘Insecure,’ Molly and Issa’s Friendship Is at Its Breaking Point

A relational therapist analyzes their toxic dynamic

After an almost two-year hiatus, HBO’s hit comedy Insecure returned with a vengeance for season four. We typically follow best friends Molly and Issa as they navigate awkward dates and somehow even more awkward sexcapades, irritating co-workers, and other personal and professional snafus. However, the opening words of this season, “Honestly, I don’t f — with Molly anymore,” uttered by Issa four months into the future, offer a glimpse into the possible deterioration of one of the most seemingly stable aspects of the show — Issa and Molly’s friendship.

Throughout the duration of the series, we’ve watched (and debated) each character as individuals and their friendship as its own entity. Though Issa and Molly’s relationship has never been free from conflict — remember Malibu and, more recently, Issa’s last birthday celebration? — the two often demonstrate an evident love and appreciation for one another, which makes this season all the more intriguing. As both Issa and Molly fight to change detrimental personal patterns, this season highlights what happens when friends attempt to adjust their roles and how the friendship, as a dynamic system, responds.

In the beginning, Issa is the friend who doesn’t have her life together, returns clothes days after wearing them, and stays working passionless jobs to make ends meet. Molly, conversely, has a professional life as a successful and sometimes too ambitious corporate attorney but struggles with translating that confidence to her romantic life, where she tends to find herself in unhealthy and unsatisfying situations. In a sense, Issa and Molly’s roles are dependent on one another. While Issa’s credit score may be laughable, at least she doesn’t fall into the same unhealthy dynamics that Molly does. And while Molly may do the most when dating, at least her work affords the opportunity to buy as many avocados as she wants and take international vacations whenever time permits, unlike Issa.

While these roles may seem flattening and limiting, they also offer a pattern that leads to a sense of safety and familiarity even if these consistent patterns are dysfunctional and constrain individual and collective growth. Interpersonal systems theory (IST), a view of systems theory specifically applied to interpersonal relationships, proposes that relationships rely on forming and following patterns to maintain system stability. As relationships evolve over time, they can become dependent on these patterns, and people are often unwilling to change for fear of creating instability or a lack of familiarity. When a member of a friendship attempts to change their role in a relationship by engaging in novel behaviors, other members in the system may fight to maintain the system as it previously functioned.

Because Issa and Molly are so accustomed to the other’s self-sabotaging patterns, they have trouble acknowledging and supporting each other when they seek to better themselves.

So what happens when these roles change? In Insecure, we witness this unfold as Issa and Molly each try to interrupt their individual patterns. For Issa, this is depicted in her desire to finally commit to her professional growth, follow through with her block party idea, and pursue a friendship with someone who’s dating her ex-boyfriend without engaging in her typical messiness. For Molly, we see her attempts at growth by entering a romantic relationship with the goal of intentionally developing a deeper emotional connection rather than merely a physical one. As Issa and Molly begin to reveal these changes to the other, they are met with harsh judgments masked as honesty and tough love. Because Issa and Molly are so accustomed to the other’s self-sabotaging patterns, they have trouble acknowledging and supporting each other when they seek to better themselves.

Historically, society has created an hierarchy for various social connections, prioritizing romantic partnerships and familial bonds and situating them above platonic friendships. But for many women who are socialized to nurture and value their social worlds, friendships offer intimacy, psychological safety, and consistency that is often experienced differently than familial and romantic relationships. These same traits, when unexamined, can also harm our friendships and quickly turn them into toxic and chaotic dynamics. When our familiarity with our friends disallows us from being surprised by them, we run the risk of placing implicit limitations on our friends based on who we believe them to be or who we believe we need them to be.

One avenue toward understanding the breakdown in friendships is conceptualizing the friendship as an evolving system. Systems theory, which has been applied to everything — families, groups, organizations, communities, and interpersonal dynamics — posits that the whole is greater than the sum of its parts. Meaning that friendships are not solely individuals coming together but that friendships are living and breathing systems with their own goals and life cycles. Specifically, this holistic perspective toward understanding relationships and communities suggests that changes to one individual within the relationship affect other individuals and aspects of the relationship.

If Issa and Molly continue to focus on their individual growth (and what the other’s individual growth means for them and their role in the friendship) rather than their relationship’s growth, there is a higher probability that the two of them will grow apart. However, if they use these changes as an opportunity to communicate the unspoken without passive-aggressiveness (or straight-up disrespectful aggressiveness) and conceive of their friendship as something larger than the two of them as separate individuals, they can translate their individual growth into collective growth. Thus, they could create a stronger friendship that’s much more complex, flexible, and accepting of their various life changes and stressors.

While friendships are often extremely powerful and even life-altering, when we conjure up images of heartache and loss, we’re conditioned to associate these feelings with romantic partners. But for many women, the pain of a friendship breakup, especially a breakup with a best friend, is like none other. Most people can readily accept that individuals grow, change, and have personal needs, yet we struggle more with the idea that friendships similarly grow, cycle, change, and have needs. Implementing a systems perspective toward friendships offers a framework that examines friendships beyond the individual level and invites us to interrogate the foundational beliefs and roles of the friendship with the opportunity to readjust them from a communal lens.

Black woman, mental health counselor, researcher, wellness consultant, PhD in counseling psychology, and Beyoncé stan. IG: black_and_woman_IG

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store