‘Insecure’: Issa Rae Is as Relatable and Conflicted as Ever in Final Season 

HBO’s “Insecure” is so sincere and true to a sector of daily life that it’s almost hard to believe this is already its final season. There’s little sense of any particular storyline winding down, because the rhythm of this series has always been so particular, as if we’re watching the characters grow and advance in real time. Creator and star Issa Rae remains at the center, still trying to figure things out in her 30s, like much of the millennial generation. Yet so is everyone else, even the characters who seem comfortable and stable in jobs that allow them to pay rent in Los Angeles. A unique portrait of the Black American professional class, “Insecure” may prove to be timeless for how it looks at life as a quirky series of steps as opposed to one seamless, confident stride.

As the season opens, Issa (Rae) is still juggling trying to be an entrepreneur while mending and breaking particular relationships. There’s lingering tensions with Molly (Yvonne Orji) and both are single again. Some funny self-reflection happens when Issa, Molly, Kelli (Natasha Rothwell), Tiffany (Amanda Seales) and Derek (Wade Allain-Marcus), attend their 10-year college reunion at Stanford University. It’s as if now 10 years isn’t the biggest game changer as everyone still seems the same in terms of attitude, although Kelli is mistakenly labeled in the program as deceased. A panel where Issa is invited to discuss her company, BLOcc (Black Lives, Opportunities, Culture and Connection), becomes more stressful and humiliating than she imagined, not least because the host and audience don’t connect with her ideas. Did she make the right choice in pursuing a dream? 

It may seem simple, but this is why “Insecure” is such a strong show. It opens a new season with characters not embroiled in plot points, but life developments. For Issa the tension of the narrative is in that relatable stress of not knowing if we’ve made the right choices in our life paths, especially when everyone else seems so set and successful. In a world where everyone is expected to get set degrees and charted paths towards financial nirvana, Issa is winging it. This means having to endure hassles like the host of the Stanford panel mispronouncing BLOcc as “Blow CC.” When Issa gets a major company to sponsor a local Black artist, she has to satisfy the (mostly white) sponsors and deal with the artist demanding his authentic voice to be left intact in a fashion show loaded with social commentary on race. But just as Issa panics, the company seems to be thrilled with such a woke radical angle. Life has its hits and misses. Issa and Molly reconnect not through the old talk where feelings are shared, but on a night out where they go partying with old Stanford friend Cheyenne, who ends up mugging both women. That’s how it happens sometimes. A battered friendship gets reunited thanks to some wild circumstances.

In this final season the early episodes don’t linger too much on the old obsessions with hazardous romance. Issa and everyone else have learned many lessons over the years and are more cautious now. Lawrence (Jay Ellis) meets Issa at LAX after her Stanford trip, but it’s not a fairy tale ending. Viewers will recall last season Lawrence impregnated Condola (Christina Elmore). Issa has become so affirmative that she admits this is just not going to work out and walks away. Later in the season Lawrence will get his own, comically wrenching episode where he deals with his consulting job and fatherhood. Having a baby with Condola is its own storm because they are not together anymore and she begins to resent his more easy-going approaches to raising a child, from quickly giving the kid solids to hoping to have him at his place for the weekend. Issa meanwhile does start moving on and gets closer to Nathan (Kendrick Sampson) the handsome owner of a barbershop she’s also supporting through BLOcc, but she’s not moving too fast, even sexually. Molly is the one fully committed to taking a break from the dating battlefield, even if her mother insists on trying to connect her with the wide-smiling, goofy church musician she’s known since childhood.

None of this sounds remotely like a show building up to some climactic finale. “Insecure” has always worked best as a chronicle of daily life for the collegial sector of Los Angeles, the residents who live on their laptops, drowned in Starbucks coffee, hoping life advancement and social change can come through startups and nonprofits. In terms of Black representation, Rae’s show offered a refreshing alternative to other, worthy but more formulaic attempts at portraying the Black middle class, like “Black-ish.” Yet its real charm is precisely in how not everything works out to perfection. We root for Issa because she’s one of the most sincerely human characters on TV. She still doubts herself and talks with herself in the bathroom mirror. She gets into bed with Nathan, but breaks down into tears, because getting over past heartbreak and life disappointments is not so easy. She has good friends who have their own baggage and hurdles. After the season premiere, the narrative even jumps ahead two years in the next episode, to show just how much and how little can change, even in a fast-paced city. “Insecure” doesn’t feel like it’s ending, even in this last round, because life is one big beat that goes on.

Insecure” season five premieres Oct. 24 and airs Sundays at 10 p.m. ET on HBO.