After the end of this week’s episode of Insecure, Natasha Rothwell, who plays Kelli and is also one of the show’s writers, joins Issa Rae for “Wine Down,” the weekly post-show discussion that airs on HBO. Rothwell describes Issa as a human game of Jenga, with the writers taking pieces from the character over the course of “Hella Disrespect” until she’s spent and unstable. As Rothwell puts it, “It’s gotta crumble at some point.”
The episode’s main event, Derek’s (Wade Allain-Marcus) birthday party, proves to be an emotional powder keg for the show’s protagonists. Exes Issa and Lawrence (Jay Ellis) must endure each other’s presence, and Molly (Yvonne Orji) plays an awkward third wheel to Dro (Sarunas J. Jackson) and Candice (Gabrielle Dennis). But Issa bears the brunt of the evening’s discomfort: By episode’s end, she’s closer to rock bottom than we’ve ever seen her, due in part to a deluge of emotional blows and turbulent arguments.
Issa’s troubles extend beyond the scope of Derek’s birthday party. At the beginning of the episode, she’s still reeling from last week’s “surprise facial.” Issa vents to Molly, “I’m embarrassed I let [Daniel] embarrass me.” Issa put herself in a vulnerable position in “Hella Blows,” and she’s peeved when she feels her trust was violated. Later, Daniel (Y’lan Noel) calls to apologize, but the conversation takes a turn when he jokes, “I guess we’re even now.” Issa is livid and, in her anger-fueled paranoia, concocts a theory that Daniel planned it all as a sort of revenge-porn fantasy.
This concept feels inconsistent with the characters’ motivations: Daniel isn’t cruel enough to plan a long-game “revenge cum,” and Issa isn’t naïve enough to think he’d be capable of doing something like that. Issa catches plenty of L’s in “Hella Disrespectful”—hell, she has been all season—but it’s hard to sympathize with this one loss when she’s being so needlessly accusatory.
The only win Issa does rack up this week is in regard to her job, and it isn’t a particularly big one. Issa finally begins making an effort to enroll Latino students at East 41st Street High School, a sea change that’s catalyzed when she learns that Vice Principal Gaines (A. Russell Andrews) has actively been discouraging non-black students from taking part in We Got Y’all. She tells her co-worker, Frieda (Lisa Joyce), “I was in a weird place for a minute and…got away from myself.” As an explanation, it’s a bit hollow, but it’s still nice to see Issa finally taking a less passive approach to a season-long conflict.
Issa’s small success at work is eclipsed by the anxiety surrounding Derek’s party. When she finds out Lawrence will be attending, her response is natural and immediate: to scour his Facebook page. Upon learning that he’s blocked her, Issa delivers her most incensed mirror rap to date. Things don’t get better that night, as the soiree turns out to be an intimate dinner party, replete with custom cocktails, assigned seats, and name cards featuring a font supposedly designed by Tiffany (Amanda Seales) herself.
So it’s to Issa’s added chagrin that Lawrence arrives with an uninvited date: his co-worker, Aparna (Jasmine Kaur). This sort of behavior reinforces Tasha’s (Dominique Perry) assertion back in “Hella Open”: Lawrence is “a fuck nigga who thinks he’s a good dude.” Lawrence may have thought inviting a date was an innocuous gesture, but let’s not forget that this is the first time that he and Issa have seen each other in weeks. Moreover, the party is made up primarily of his ex’s friends. The awkwardness seeps in when the dinner guests have to shift their chairs over in order to make room for Aparna, disrupting Tiffany’s planned out seating arrangement.
Tiffany’s precise execution of her husband’s party makes the scene an ideal setting for all of the simmering tensions at play throughout the episode. She and Derek hold court in the middle of the room, putting their supposed perfection on display. It’s been implied that they’ve had problems before, but Tiffany is above all concerned with creating an image of perfect coupledom, which flies in the face of their single, philandering, or heartbroken guests; none of them are close to achieving Tiffany and Derek’s lofty aspirations of foreclosing on a fourplex in Inglewood. It’s also significant that the party is made up entirely of couples, save Molly, Issa, and Issa’s younger brother. And due to a tepid argument between the two friends at the beginning of “Hella Disrespectful,” they barely speak to each other at dinner; Issa brought her brother as a faux-date buffer, leaving Molly to fend for herself.
Molly’s comparative loneliness leaves her in a particularly vulnerable position at the dinner party. It’s the first time she’s seeing Candice since she and Dro began their fling (formerly a one-time thing, now more of a “17-time thing”), and the two women share some incredibly awkward small talk during cocktail hour. When Molly meets Dro in the bathroom for a mid-party romp, it becomes clear that Dro isn’t treating his open marriage as admirably as he should be, if in fact the open marriage alibi is even true. And when Dro slinks back to the table and suggests that Molly wait behind as to not rouse suspicions, Orji’s face expertly morphs from pleasure to regret. The relationship is beginning to stink of sleazy affair more than idyllic polyamorous romance, and Molly finally calls it off. But not before she calls back her mother, whose advice pushes her to end things with Dro.
While things end on the upswing for Molly, Issa continues to crumble. She gets into a bitter fight with Lawrence outside of the restaurant, each of them hurling insults at the other and exposing deep-seated resentments. She brings up his failed app and former financial dependence on her, to which he calls her a “fucking ho.” It’s a nasty exchange but ultimately the most honest they’ve ever been to one another.
When Issa returns home, she’s met with a rent-increase notice. That, and a glance at the burn mark on her ceiling, sends Issa into a rage, and she trashes her apartment. That Issa reaches her breaking point is justifiable, but it seems like her fight with Daniel is mostly on her, and that undercuts the severity of her tailspin. The final moments of “Hella Disrespectful” set up two options for Issa going forward into Insecure’s season finale: Either she’ll be resigned to her station and her apartment will remain in ruins, or she’ll take ownership of her actions, clean up, and move on.
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