It’s been almost a year and a half since the Season 3 finale of “Insecure,” creator and star Issa Rae’s funny, tragic ode to adulting. That adds up to nearly 80 Sundays without the hilariously familiar and infuriating antics of the HBO show’s central characters: Issa; her BFF, Molly; her ex-bae Lawrence; and the rest of their South Los Angeles crew of 30-somethings on the verge of being grown. So even the most zealous Team Lawrence (raises hand) or Team Issa fan can be forgiven for having a few questions. Where does Issa live again? Is she working? Did Tiffany have that baby? Is Dro still lurking in the wings? Consider this “Insecure 101,” a prerequisite course before this Sunday’s season premiere.
Season 3 began with Issa crashing on Daniel’s couch and ended with our girl finally organizing her new apartment. Let’s hear it for Issa’s personal growth — even baby steps like taking the plastic off her couch and organizing her record collection.
On the relationship front, Issa had finally ended things (all things) with Daniel and grown close to Nathan, an L.A. transplant she met while making her Lyft rounds. But things were left uncertain between Issa and Nathan after he ghosted her — a subplot that was only kind of resolved in the season finale, when a contrite Nathan confessed he had isolated himself because he was struggling with depression. Issa certainly could have handled the revelation with more compassion than calling it “a bad mood,” but she didn’t completely shut the door on her latest love interest.
Of course, this wouldn’t be “Insecure” if Issa wasn’t still attached to Lawrence. Their connection is on display every time they run into each other — like their sweet and easy banter at an outdoor screening of “The Last Dragon” that served as Issa’s low-key 30th birthday party. We expect the fourth season to escalate the tension between these two, and we have at least one idea of how the “Insecure” writers will do that: Issa became fast friends with Condola, the woman who organized “The Last Dragon” event, and felt renewed excitement about her vision of a block party celebrating black L.A. Condola also happens to be the woman who went on a date with Lawrence at the end of the finale.
If “looks good on paper” was a woman, it’d be Molly. She’s the gorgeous and ambitious lawyer with the perfect highlights, designer clothes, CB2-decked-out apartment and cute dog. But having it all has never been in the cards for dear Molly. Since Season 1, our intrepid career girl has never been able to find a man who checks every one of her many, many boxes. If she isn’t dumping a good guy (Jared), she’s ducking into a bathroom stall with the wrong one (Dro). It’s her superpower.
At the end of Season 3, Molly is left confronting her instincts after canceling yet another potential match (Andrew) for the mysterious crime of “doing too much” and burning bridges at her new firm in the name of climbing the corporate ladder. “This is just how I have to be,” Molly tells Issa in their last scene together. “Is it?” asks Issa. “What’s your end goal?” It’s one of the pair’s many come-to-Jesus moments, and more proof that Molly and Issa’s relationship is the core one of the series. Season 3 leads us to believe Molly may have finally gotten the message, though: She calls Andrew after writing him off and explains that maybe she was wrong.
Like his ex, Lawrence is still trying to find his true path. He seems to be on the right track, working his way out of underemployment and trying the dating thing in earnest instead of being a cad (see: Season 2). He and Issa have finally reached that awkward, post-relationship stage of interaction, but their chemistry is still there. As we saw in the Season 3 finale, Lawrence also has chemistry with Condola, who has absolutely no idea that she went on a promising date with the man Issa dated for five years.
The resident bougie girl of the “Insecure” crew, Tiffany never minces words. When we last left her, she was basking in the glow of her pregnancy (complete with a Beyoncé-inspired photo series). At her baby shower, Issa, Molly and Kelli learn that Tiffany, the only married one of the group, has an entirely separate clique — “the crazy crew” — reinforcing the idea that Tiffany’s life as a wife and mother will veer away from the rest of the girls. When Issa and Molly complain about being left out of the shower-planning loop, Tiffany counters that neither of them asked to throw her one. Issa, who quit her nonprofit job in Season 3, claims she had too much going on. “So. I’m having my first child,” responds Tiffany. “We’re always going to have life s---.”
Kelli’s just out here living her — and probably your — best life, okay? She’s also godmother to Tiffany’s child, which should be interesting to see, especially alongside whomever Kelli is dating in Season 4. Because you know there will be at least one new (completely smitten) guy in her life.
All the boys they loved before
Dro, the married childhood friend who Molly got involved with, is having a baby with his wife — a fact Molly learned at Tiffany’s baby shower. Needless to say, the pair are not on good terms. Jared, another one of Molly’s near-misses, is happily in a relationship (from the looks of things) with a woman (a blow to Molly’s dysfunctional gaydar). And then of course there’s Daniel, the “itch” from Season 1 that blew up Issa’s entire relationship with Lawrence. Daniel swooped in when Issa needed a couch to surf on following her financial downturn, but the two never got an actual relationship off the ground. The music producer simply faded into the background as Season 3 went on and Issa moved on with a pre-ghosting Nathan.
Issa hasn’t lived at the instantly recognizable Inglewood apartment complex since Season 2, but it’s still part of the show’s DNA, along with the oddball characters who live there, like our favorite resident of the com — er, bomplex — Thug Yoda.
“We Got Y’all”
At the beginning of the series, the audience is introduced to Issa through her work at “We Got Y’all,” a well-meaning after-school program serving “inner city youths,” where Issa is the only black woman. Halfway through Season 3, Issa, who’s still searching for her passion, quits, breaking up with the place like a boyfriend gone bad. “I’m sorry, I can’t do this anymore.” Her next move? The block party! Oh, and also property managing — it’s how she’s able to afford that mid-century one bedroom.