‘Insecure’ Season 5, Episode 1 Recap: No Time to Be Insecure

During the first episode of the final season of HBO’s “Insecure,” we meet “Throwback Issa,” the college-aged version of Issa staring back at her in the bathroom mirror.

This time, Issa doesn’t rap to her reflection. Instead, they catch up and she looks at her younger self endearingly. “I forgot how cute I looked with twists,” Issa says to her reflection. And the younger version of herself is struck by who she’s become. “Issa?! Is that me?” she asks.

After they spend a minute admiring their teeth, they awkwardly cut one another off, as if they are both thinking and doing the same thing. In this tango you can tell that while Issa does not look like she used to — now she has a more auburn hair color and doesn’t wear braces — she is very much the girl she used to be, in essence.

“Throwback Issa” was the most literal reflection upon the past in an episode set at Issa and her L.A. crew’s 10-year-reunion at Stanford, their old stamping ground. The crew looks as good as ever. Kelli and Tiffany in Gucci? Yes. (Tiffany only wore pink and green the entire episode). Issa and Molly in classed up Stanford sweaters? An aesthetic I can subscribe to.

It was a weekend that involved plenty of time traveling. We saw college Issa admiring but also being slightly disappointed in current Issa. Later, on an alumni panel, current Issa worries about future Issa’s time to do the things that she wants to do. Molly finds herself thinking back about her younger, more bullish self. Kelli flies too far into a future where she no longer exists, and doesn’t like her legacy. The characters are looking back to see how far they’ve come and learn where they want to go.

The episode also picked up the pieces of the more recent past. Last season, we left Issa in an entanglement with Lawrence, who had recently found out that his ex, Condola, was pregnant. At the time, Issa was considering moving to San Francisco with Lawrence, who had just found a job there. The pregnancy was a brick thrown through the window of their relationship.

Issa and Molly’s relationship, the one viewers tune in for, was on thin ice and the heaviness of their love lives threatened to fracture it. Their dreamy hangout scenes were gone — now there was only awkwardness.

This week there was movement on each of these fronts. Issa and Molly are in agreement on what they want: to move forward, to grow past the obstacles in front of them. They are done trying things on, they know more about who they aren’t and what they don’t want in their lives. “I know you’re a big-time lawyer now,” reflection Issa says. “No, I never really wanted to be a lawyer,” current day Issa responded, with a certainty that escaped her younger self.

During the panel, Issa is joined onstage by a filmmaker, a start-up founder and the advertising art director at Coca-Cola, all alumni. Issa was invited as an entrepreneur and founder of “The Blocc” — we don’t know much about the company (and it’s not clear if she does either) but I love this for her.

When the moderator asks the panelists when they found stability in their life, Issa doesn’t have an answer. She is honest with her audience and tells them that she’s unsure and that she may be wasting her time, but she’s also talking to herself. It’s as if by hearing herself talk about her latest endeavor, she comes to understand the risks associated with it in a way she hadn’t before.

Throughout the episode, Issa is so focused on her future and past that she is incapable of being present. Whenever she is asked what the name of her company stands for, she stammers, unable to remember. She may have her own company now, but she is still managing apartments and driving a Lyft. This all appears hard for Issa to reconcile but I get the impression that she eventually will. This isn’t “Game of Thrones.”

Back in the quad, Molly, three-months after her break up with Andrew, is trying to be a good friend to Issa because that’s what Molly needs from her. After the struggles of last season, Molly now seems ready to triage the friendship, softly asking Issa, “Are we going to be OK?”

Molly also seems to be caught in a flashback on campus. While on a walk with Issa she remembers the confidence that she used to have. “Freshman year, we thought we had it all figured out.” The fire that used to define her, her tenacity and ambition, is absent. But I doubt that it’s gone forever.

Kelli, on the other hand, is believed to be dead by the organizers of the reunion — she was marked as deceased in the program and even appeared in an in-memoriam video. (“Stanky Legg” by the GS Boyz plays in tribute when her face appears.)

At first, she thinks it might be good for her to “go off the grid,” but then something else sets in. When she realizes that she is only remembered for her allergy to kale and solid stanky leg, it stops being fun for her. Kelli’s modus operandi has generally been to go with the flow, but maybe it’s time to swim upstream.

When the girls are on their way to Reggae Gold, an old haunt in Oakland, Kelli is not as amped as the other girls. She is obviously disturbed and interrupts a singalong to The-Dream’s “I Luv Your Girl,” an on-the-way-to-the-club ritual, to let them know why she isn’t feeling the party vibes. She is quickly dismissed. Maybe playing pretend dead hit too close to home for her.

The next morning at a diner, they give Kelli an appropriate in-memoriam tribute. When they leave, Molly and Issa walk past three young giggly girls, one carrying a poster that read “take action.” The girls apologize for bumping into them. Issa looks back at them as if they seemed familiar, it was like seeing their younger selves walk right past them. As those girls fade behind them, Issa and Molly tell one another they want to move forward.

Then Issa proceeds to do so. When she flies home, Lawrence is waiting for her at LAX in a black hoodie, looking sorry and feeling sorry. (Yes, I’m still mad at Lawrence for getting Condola pregnant while trying to mend things with Issa.)

What is different about Lawrence’s pitifulness is that Issa is no longer willing to take part in it. She breaks up with him and he immediately understands. The breakup was quiet — no arguments or shock, just an understanding between two adults. It was a more mature and cleaner breakup than their traumatic first one.

Time is running out for “Insecure” and perhaps also, the premiere seemed to suggest, for maybes and half-steps as the characters consider the direction of their lives, beyond young adulthood. There’s not much time left to be insecure.

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