'Insecure' isn't falling off — we just aren't keeping up

When Insecure returned for its fifth and final season on HBO in October, the collective anticipation on my timeline almost instantly turned to collective disappointment. It's worth mentioning that both my Twitter timeline (the journalists and content creators who made up Black Twitter 1.0) and my Facebook timeline (25-50 year old professionals in music, media and academia) are technically the show’s target demo. From the time we were introduced to an "awkward AF” Issa Dee five years ago, the show had become appointment TV for a group of viewers who have leaned fully into the age of the binge watch.

Yet after a 16-month break that certainly felt longer — because, pandemic — the love was apparently gone. "Reunited, okay?," the official beginning of the end, left the timeline overwhelmingly underwhelmed. Having missed the appointed time for the Season Five opener, the online chatter didn't quite inspire me to jump onto HBO Max and get caught right away. After two more weeks of similar reactions, I finally dove in. And for the past six weeks, I've been silently, shamefully enjoying the show alone, wondering where all of these complaints are coming from.

The primary criticism I've seen about this new season has been about the writing. But for eight episodes now, the show runners have been developing at least six strong concurrent storylines tackling issues including mental health, co-parenting, estate planning and career insecurity — no pun intended.

Then it hit me last night: the quality of the writing hasn’t changed, the characters have evolved. And maybe, hopefully, so have we as an audience.

I confirmed my theory by going back to the very first episode of the show from 2016, where we met a then freshly 29-year-old Issa, smack-dab in the middle of a “quarter-life” crisis. The unfulfilling, micro-aggression riddled job, the stable relationship purgatory, the friend envy: at 29, Issa Dee’s worldview was exactly where many of us found ourselves as we approached 30. In the latter half of our 20s, many of us looked at the top of our next decade as a life goal. You expect to be a fully-formed grownup at 30, one who’s got life fully figured out from career to finances to romance. Then most of us hit 28 or 29 and realize, like Issa when we met her on Insecure, that we still have a lot of stuff to figure out. And only a handful of us are blessed to be close enough to a character like Molly to realize that, even those about-to-be-30-year-olds who seem to have it all on lock, still have strong moments of self-doubt about various parts of their lives.

At its onset, Insecure resonated with so many of us because of its fresh perspective on twentysomething-hood and its South Los Angeles setting, after decades of TV exclusivity to New York City. But it also landed with such a wide audience because many of us were either right in the middle of that part of our lives or had made it to the other side with enough wisdom to realize that we might not ever feel like full grown-ups. The seriousness with which people in their late 20s and early 30s take their lives makes for great TV, especially when presented through a lens that allows viewers a peek into the less-than-perfect parts of the characters' lives.

If you were to revisit S1 E1 of Insecure as someone who’s kept up with these characters over the past six years of their lives — S5 E2 jumped us a year into the future — you would likely find both Issa and Molly unbearable. And you’d be screaming for Issa to remember that she once referred to Lawrence as “the guy I’m not going to end up with.”

Even when last night’s scenes with Molly and Kelli helping the Carters with their estate planning felt like the “very special episodes” of 90s sitcoms, I recognized the conversation that was happening as one that is very real and very needed. I also recognized that those less-than-exciting moments in life are essentially the reality of most people’s mid-thirties. There’s a whole lot of ordinariness to that period of life, even when life is popping, your new relationship is blossoming and your career is on ten. Every co-parenting situation doesn’t have to be toxic or lead to a reconciliation. And sometimes, moving in with your partner can be scary… but not in a “run-for-the-hills” kind of way.

Rewatching the first few episodes of this season evoked the same chuckles at culturally relevant moments and the same memories of parallel life events as I had experienced with previous seasons. Issa and her crew are growing, in a mostly healthy way — something we don’t really see on television too often. And I, for one, am happy that today’s mid-twenty somethings have this crew as a point of reference, versus the ladies of Girlfriends or Sex and the City. Ask almost any woman over 35 who loved those shows during their heyday: we’re unpacking a lot.

For the first time in my career as a fan and amateur TV critic, it looks as though I am being offered a shot at closure for the characters who have become almost as real a part of my life as the countless social media friends I’ll never meet in person. And I love to see it.

If you, like so many on my timeline, have given up on season five, go back and revisit season one and see how far we’ve come.