Issa Rae’s ‘Insecure’ Says Goodbye With a Vivid Sense of How Lives Transition and Keep Going

Alci Rengifo

There are many ways to define closure. It can mean saying goodbye to life one used to have or it can simply mean a transitional period into uncertain but changing territory. The series finale of HBO’s “Insecure” touches on these points with the same kind of welcoming, vivid sense of Black millennial life that has made it such a unique show. Since its first season, star and creator Issa Rae has defied TV convention by daring to forgo the usual plot devices. Instead “Insecure” captures the very rhythms of life in a modern city like Los Angeles, where lives are ambitious and plagued by insecurities. The series finale doesn’t contain shockers but it does have the kind of surprises any viewer could experience during transitional periods. For people in the real world, a “season finale” can mean finally charting a definitive path towards a particular life goal.

“Everything Gonna Be, Okay?!” begins with Issa (Issa Rae) having a final, defining car ride back home with Nathan (Kendrick Sampson), who feels dejected after a scuffle involving Issa’s ex, Lawrence (Jay Ellis). Nathan feels caught in a toxic triangle where it’s obvious Issa hasn’t let go of her feelings for Lawrence and so he decides it’s time to step back. For Issa this means falling into another one of those moments of limbo, where she sees herself as stuck while everyone else appears to be moving on with life. She begins to feel maybe she should get away from Los Angeles for a while. Molly (Yvonne Orji) tries to raise her up by pointing out how far she’s come. Even if her love life is a mess, Issa’s drive to continue building her company, Blocc, is paying off. At a birthday thrown by her friends, donors quickly give $5,000 to the venture. Nathan also arrives to apologize for the way things ended, because not all relationships have to end in full acrimony. The rest of the episode will progress this way, with individuals simply transitioning into new phases without bombast.

“Insecure” has worked as such a sharp representation of Black life in L.A. by being a broad portrait. Rae wanted to tap both into a community’s experiences as well as those of an entire generation. The trials of being Black in America for millennials also combine with the overall need to compete in an unforgiving economy, in this show it happens in a city where everyone is defined by career, income and looks. Issa is a Black woman finding her own rhythm even as everyone else seems to skate by through convention. Tiffany (Amanda Seales) and Derek (Wade Allain-Marcus) are now living in pristine Denver suburbia, although Tiffany complains her daughter is the only Black student at school. She also isn’t keen on the idea of being a housewife without a job. Molly seems to have found real happiness with Taurean (Leonard Robinson) and before the episode is over they tie the knot. Kelli also finds romantic stability with boyfriend Desmond, and at her birthday dinner announces she’s pregnant. Kelli has always been one of Issa’s friends so full of life, but now she admits being with Desmond has helped her open up in new ways to new possibilities, like motherhood. Kelli also takes a job offer from Molly. For Molly a major life change also occurs when she receives a call from her brother informing that her mother has died. Joy can also come with heartbreak. It’s just the way it is.

With all of these personal changes going on around Issa, she remains the underdog we root for because it’s not easy and simple for her. She meets a new man, Nasir, at her birthday party and he seems like the match anyone in this city would approve of. He’s handsome, fit and has a good job. And yet Issa is still tormented by the projection of herself in the mirror always pointing out her faults and missteps. Just as she’s about to spend a night with Nasir the phone buzzes and it’s Lawrence. Something that plagues Issa, and makes her so human and relatable, is that she knows what she wants, yet there’s always that insecure hesitancy that holds her back from these major leaps. But the leap comes when Issa is working on the new Blocc office and Lawrence drops by and they have a definitive talk, the one where they decide to finally, really give it a try.

The final then leaps a year and here is where the show reaches a proper conclusion. We make our decisions and see how they pan out. So a year later Molly and Taurean are having their big wedding reception, Issa and Molly have a tearful moment sharing how much they mean to each other. It’s that kind of goodbye we all have to go through, where it’s not a final parting, but we just know a friend is moving into a new phase. Yet Molly isn’t the only one going through an important transition. The closing scenes give Issa the curtain call she deserves. We see her driving off from the new Blocc office in a Lexus, past  living and work spots and coming home to Lawrence and his young son, Elijah. Success has arrived. 

“Insecure” never tried to be a socially radical series, and thus provides an ending that captures a particular idea of arrival and contentment for millennial society. We define finally finding our footing in having a good salary, a decent home and all those other check marks of the American capitalist dream. But we can’t fault Issa for getting there. She never sold out and worked hard. She always marched to the beat of her own drum too. The final moments also define a different kind of happiness. She talks to Molly, who is also content, vacationing in Greece with Taurean. Two friends share their joy and a bond that distance can’t break. “Insecure” ends on a note that is almost the perfect millennial daydream. In a society where climbing the ladder is such a challenge, bliss can mean not worrying about the rent while sharing carefree laughs with your best friend over the phone. Rae’s show will be an interesting time capsule to revisit over the years. Viewers will look back at it not wondering about possible plot twists, but about how we in this time period thought, wanted, dressed, associated and felt amid expectations and deep insecurities.

“Insecure” series finale airs Dec. 26 at 10 p.m. ET on HBO.