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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…