Issa Needs to Learn the Importance of Boundaries

We see this play out within the first few minutes of the episode. When we last left Issa, she’d moved in with her old friend (and hookup) Daniel after getting priced out of her apartment. The camera zooms in on Daniel’s smooth backside while he’s having sex with a woman whose face we don’t see, but can only assume is Issa. Seconds later, the truth is revealed: Issa is wide awake on a couch in the living room. Daniel is sleeping with someone else.

Only two weeks have gone by in the world of Insecure, but that’s plenty of time for one to establish what is and isn’t cool with a new roommate. Issa is bothered by the situation, perhaps because it interrupts her sleep, but more likely because she and Daniel have unfinished business. She’s not ready to rekindle what she temporarily had with Daniel, but she’s also not comfortable enough to accept the excessive volume of his late-night trysts, either.

Thus, boundaries are established, and Daniel agrees to shoot Issa a heads up next time he’s with a woman. It’s a simple solution, one anyone who’s lived in a dorm room understands, and yet something feels wholly incomplete about the arrangement. What does Daniel honestly think about Issa? What boundaries did Daniel need to set to accept Issa back into his life? We never learn, as Daniel never expresses his needs. He merely acts out in a passive-aggressive manner (like calling Issa "roommate") and hopes it makes an impact. Being friends with benefits, or even just friends, may be too much for Daniel.

Issa’s best friend Molly, too, has established her own new set of boundaries—and in a pleasantly surprising turn, they’ve been healthy rather than toxic thus far. In season one, we saw Molly’s extreme limits (and biphobia) derail her from having the sort of loving, fulfilling relationship she’s always wanted. In season two, perhaps in response to her season one relationship loss, Molly throws caution to the wind and dives head-first into a complicated "thing" with her childhood friend Dro, who is in an open marriage. Whereas Molly did everything in her power to protect her misguided beliefs about what constitutes the "right relationship" in the past, this season, she’s abandoned her old beliefs.

It was not until last season, when Molly left her toxic workplace full of blatant sexism and racism, that she began a turnaround. Leaving a job that refused to acknowledge and pay her for her talents was a way that Molly set boundaries for herself. No longer would she accept a "good enough" job—Molly knew she was worth and deserved more, and made the necessary changes to make that a reality. Now, she’s established even more boundaries, as illustrated by her beach vacation where she tells the anonymous bae she met there that what they had was only temporary.

But pulling away from Dro would require more effort, confidence, and assuredness in her decisions from Molly. After Dro repeatedly overstayed his welcome and told Molly not to "worry about what me and my wife do," Molly asks him to return her key. Why would Molly have given a non-husband, non-boyfriend a key to her apartment in the first place? And more importantly, why is Dro so hesitant to give her key back? For Dro, boundaries are only valuable when they protect his marriage—not when they interfere with what he wants from Molly.

Molly’s assertion of boundaries is an act of self-love. We’ve yet to see Issa fully inhabit that same self-love in seasons two or three. Instead, Issa has fallen into an excruciating cycle of self-punishment, allowing mistreatment to flourish in her work life, her friendships, and her romantic life. In the office, she lets herself be the scapegoat of her nonprofit's failure to connect with non-Black students. Why exactly, though, should Issa bear the entire burden of connecting with every student? And why does she allow her two white bosses to place her company's failing retention rate squarely on her shoulders as if they are exempt by their position in the company? We know Issa is talented and hardworking, yet she continues to work for an organization she seems to hate. Rather than search for a better, higher-paying job, Issa makes money on the side as a Lyft driver, a position that, among other things, also involves cleaning up other people’s vomit and trying to stop fistfights. How much should one person endure in order to "correct" their past mistakes?

Some of Issa’s self-punishment is warranted (particularly in how she has treated both her ex and Daniel), but when does guilt turn into self-sabotage? When are you no longer able to move forward because you are so stuck on your past mistakes? We are witnessing two sides of the same coin in Issa and Molly, but only one character is embracing real, genuine change in her life.