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‘Insecure’ Is Reexamining All Relationships, Past and Present

A run-in with her longtime ex-boyfriend and a fraying relationship with her best friend leaves Issa searching for someone to connect with

HBO/Ringer illustration

“I just wish it wasn’t always one piece missing, man,” Insecure’s Lawrence says while driving through Los Angeles. “If it’s not the relationship, it’s work. If it’s not work, then it’s some other shit.” Six weeks into a worldwide quarantine, I’m going to say Lawrence doesn’t know the true extent of “some other shit.”

If any character on Issa Rae and Larry Wilmore’s Insecure has earned the right to grumble over the relentless calamities of adulthood, it’s protagonist Issa Dee. We’re not far removed from her days working at We Got Y’all, a nonprofit that seemed to churn out less community support than coworker microaggressions, nor are Issa’s failed flings too far in the rearview either. Some, the show teases, might not stay in the past. Who knows? Through four seasons, Issa’s never been less concerned with love.

Instead, Issa is focused on her long-conceived passion project, a block party to showcase community artists and local businesses. It’s all-consuming; Issa is too absorbed with planning the event to give her full attention to anything—or anyone—else. Three episodes in, the only romance Issa indulges in is a dick appointment with a TSA agent who leaves immediately after the act. Refraining from new affairs doesn’t absolve Issa from past bad relationships, though, or from their ensuing drama. It just gives space to reexamine the people already in her life.

In Sunday’s “Lowkey Thankful” episode, which takes place around Thanksgiving and induces much nostalgia (the Insecure world is still gathering in large groups, grocery shopping without armed guards, and posting IG videos of other people, not sourdough starters), the actual planning for the block party is put on pause. Issa runs into Lawrence, her ex, at a lunch spot. They begin cracking jokes before Lawrence’s current girlfriend, Condola (who is also Issa’s consultant for the block party, a partnership that happened before either realized the other’s involvement with Lawrence), walks in. There’s obvious unease all around, despite the three of them trying to will the situation to normalcy with smiles and small talk. In Episode 1, Issa insisted that everything was fine. But you can’t erase history, or in Issa and Lawrence’s case, five years of history.

The discomfort manifests differently for both women caught in the triangle. After Condola’s Friendsgiving prompts Lawrence to ask whether she’s over her ex, she turns the question around. “If anyone should be worried about an ex, it should probably be me,” she says, mentioning his and Issa’s familiarity in the restaurant. “You and Issa have little jokes, and you have the same friends. How do you think that makes me feel?” Meanwhile Issa tells her brother Ahmal at Thanksgiving dinner—consumed at a Mexican restaurant after the two opt out of family time—that the interaction with Lawrence and Condola left her with understandable resentment.

“The person he is now is not the person he was with me,” Issa says. “Like they were out to lunch, and I’m pretty sure he was going to pay. I never got that.” If that sounds like the bare minimum, welcome to #TeamLawrence vs. #TeamIssa. “I got the work-in-progress,” she says. “It took a lot of support and patience. And I feel like she’s reaping all the benefits of his time with me.” It’s a common feeling after seeing an ex, if you can get past seeing red or feeling blue, and in Issa’s case, the bitterness is justified. The new version of Lawrence fixes the sink, wears expensive shirts to dinner parties, pays for meals, works for a tech company, and complains about his promotion being delayed. Issa’s Lawrence was unemployed and fastened to their couch.

“You have a right to feel however you want to feel,” Ahmal says after Issa opens up about Lawrence. “Seriously.” It’s a tender moment for Issa and Ahmal, whose “love you/hate you” sibling bond is usually exhibited in sarcastic remarks and playful one-offs at the expense of the other. That the show chose for Issa to confide in Ahmal and not Molly, her longtime best friend, speaks to their actively fraying connection. This season, Issa and Molly’s friendship is Insecure’s most exhausting relationship—old friends without the free time or fresh perspective to understand the changes going on in each other’s lives. They’ve clashed in past seasons, but the underlying tension is stronger than before. In Episode 3, after exchanging a series of shots and slights in the grocery store, Molly and Issa agree to talk through it later over pie. At the episode’s end, Issa asks, once again, if they can settle their differences at another time. Her relationship with Molly has been taking more energy than it generates, and the day’s already been long and full of feelings.

In the restaurant, Issa looks at her brother with gratitude, like she’s been heard, like she feels validated, like it’s the first time in a long time that a confidant has made her feel that way.

Disclosure: HBO is an initial investor in The Ringer.