Two Major Crossroads — And a Shocking Twist — on “Insecure”

By Terrance Turner

June 15, 2020

Tonight’s episode of Insecure (“Lowkey Lost”) was even more eventful than last week’s. Tonight’s jumbo-stuffed episode threw viewers more than a couple curveballs: two main characters’ relationships reach major crossroads, and one supporting character faces a very real crisis — one that affects millions of women across the world.

At a market, Lawrence informs Issa that he got the job in San Francisco. Issa is elated for him, but Lawrence questions what this means for the relationship. “Is the distance a deal-breaker?” he asks.

“No, it’s not,” Issa responds. “San Francisco’s a 45-minute flight, and you know, if things stay good between us, who knows? Maybe I could [move],” she suggests.

“What about your work? Or your family, your friends?” Lawrence asks. 

“I can make new friends,” Issa responds. “I might need to.” 

She approaches Lawrence with a dead-set gaze. “Honestly, I’m at a point in my life where I just want to cut out the bulls–t and surround myself with things that make me happy. Like you. So if we want this to work, it’ll work.”
“Good. ‘Cause I want it to work, too.”

Having just left her lovey-dovey meeting with Lawrence, Issa travels to Nathan’s barbershop. For what reason, I wondered? Was this going to be the moment that Issa sabotages her chance for happiness with Lawrence (again)? Would Nathan make a move and force Issa to choose? No. It turns out that Issa just wants to evaluate Nathan’s barbershop space for a future event. (Event planning does seem to be a potential career path for Issa these days.)

He apologizes for throwing shade at Lawrence in the previous episode (calling him “sometimey”, like Nathan didn’t turn into Casper the Ghost last season). “I get that I messed up,” Nathan admits, adding that hearing news of her getting back with Lawrence hurt him more than he expected. Issa understands that, but she’s not about to offer him any false hope.

“I really want to be a good friend to you,” Issa says, “but I’m with Lawrence now. So if that’s too much–” 

“It’s not,” Nathan interrupts. “I just wanted to be honest about how I felt, and the last thing I want to do is make your life more complicated.” 

So what we thought would lead to a betrayal of Lawrence turns out to be perfectly benign: Nathan is respectful of Issa’s relationship and content to be her platonic friend…at least for now.

Molly brings Nathan to a work event and a colleague invites her to an after-party of sorts. Andrew doesn’t want to go, but Molly sweetens the deal by offering to have the bartender play one of his artists. Andrew agrees, but it’s yet another inconvenient sacrifice for the relationship, and his resentment is building. Later, when they return to the apartment, Andrew wants to watch the ”Looking for Latoya” reunion. Molly is tired and just wants to lay down. ”I won’t give anything away,” Andrew promises. But she doesn’t want him to watch without her. It’s yet another instance of them not being on the same page. 

“You know, if it was me who wanted to stay out longer today, it would have been a whole thing,” Andrew says. So… what’s the problem? 

“Every time I mention something that bothers me, you just dismiss it,” he complains. “But I’m supposed to bend over backwards when it’s about you.” Molly somehow doesn’t see how Andrew’s “bending over backwards.” Like he hasn’t been doing that since the minute they met.

“I do whatever you want, Molly,” he complains. “It’s getting old.”

Their fight (the second one they’ve had in two episodes!) is interrupted by a (frantic?) call from Kelli (Natasha Rothwell). Their mutual friend Tiffany DuBois (Amanda Seales) is missing. Molly joins Issa, Kelli, and Tiffany’s husband Derek in a frantic search for the missing mother. They spend nearly all of the episode’s midsection looking for Tiffany, visiting bars, restaurants, and surveillance cameras. And when they finally find her, she’s nothing like the Tiffany they used to know.

* * *

The signs of postpartum depression have been there all season — Tiffany not properly bonding with her baby, joking about leaving her at the fire station — but everyone missed them. (Which speaks volumes about the depth of her friendships with these girls.) So the (wo)manhunt for Tiffany exposes a blind spot that everyone involved seems to have.

The search for Tiffany is also a nifty way of bringing Issa and Molly back together. They’re forced to coexist while on the hunt. And Derek’s words about losing Tiffany parallel what these two friends have been through this season. “I knew she wasn’t happy,” Derek muses, “but I thought time would fix it.” While listening to him, Issa and Molly realize what their friendship means to them.

They eventually reconnect at the episode’s end, after both have been blindsided by game-changing news about their romantic relationships. That was part of the design, according to writer/director Prentice Penny:

The problem is that we viewers (at least this one) are no longer invested in Molly and Issa’s friendship. They clearly aren’t on the same page: Issa is frustrated because she’s the only one putting in effort, while Molly seems bothered that Issa hasn’t asked for an apology on bended knee. It’s crystal clear that the only reason we see these two (finally!) talking it out at the end is because both their relationships have hit the skids. Which is such a healthy foundation for a friendship to be rebuilt on.

And that’s just that on that.

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