“You frame a lot of things in your life with ’should,’” Dr. Rhonda Pine (Denise Dowse) says to Molly (Yvonne Orji) toward the beginning of “Hella Questions,” the latest episode of Insecure. The therapy session is considerably different from the one we saw in “Hella Great,” in which a tight-lipped Molly assured her therapist that everything was fine. Spurred by the realization that she’s making less money than Travis (David Hull), her colleague and physical manifestation of white male mediocrity, Molly begins to open up to Dr. Pine, revealing more about herself than she realizes. Dr. Pine asks Molly if she’s heard of “magical thinking,” which is, as she puts it, when we believe what we want will influence the external world as opposed to accepting things as they are. “If those ’shoulds’ didn’t come to fruition,” she asks, “would you feel comfortable with your life looking a different way?”
“Hella Questions” is primarily concerned with making sure those “shoulds” do come to fruition, and not just for Molly. The episode sees the three main characters—Molly, Issa (Issa Rae), and Lawrence (Jay Ellis)—moving away from stagnancy and toward action. Molly’s surge of proactivity comes about in the workplace. She realizes good things won’t happen to her simply because she deserves it, so she makes a concerted effort to access Merrill, Johnson & Schwartz’s seemingly impenetrable boys’ club, who gather at what can only be described as the platonic ideal of a white male space: a hockey game.
For a minute, it seems like Molly is about to become a big L.A. Kings fan, but her small talk and smooth faux-enthusiasm can’t carry over into work the next day, where the hockey-loving partner is cold to her attempted chumminess. Instead of wearing herself out trying to be a member of a club she may never perfectly fit into, Molly ultimately opts to strengthen the bond with her female boss at the firm’s Chicago office. It’s the sort of positive change that, prior to Dr. Pine’s counseling, Molly might not have pursued.
The episode also serves as a wakeup call for Lawrence, who’s been free-floating since the events of Insecure’s season one finale. This is certainly true of his living situation: He’s crashing on an air mattress at buddy Chad’s (Neil Brown Jr.) place during the week and staying with Tasha (Dominique Perry) on the weekends. Largely owing to Lawrence’s insouciance on the matter, Tasha falls somewhere between fuck buddy and girlfriend, a distinction that Lawrence doesn’t seem to be in any hurry to define. He also hasn’t given Issa any closure since their tryst last week (nothing says free-floating quite like your ex calling your hookup a “nebulous fuck”).
Lawrence, however, undergoes a sea change over the course of “Hella Questions.” He finds an apartment that, despite his initial indecision about it, he commits to by the end of the episode. More significantly, he commits to Tasha, a decision that bumps her up from lowly hookup who cries out “zaddy” during sex to bona fide girlfriend.
Not every moment in “Hella Questions” shows our protagonist making palpable shifts from stagnancy to change. Things seem to be looking up for Issa at work, where the school’s vice principal, Mr. Gaines (A. Russell Andrews), steps in to help improve attendance. But Gaines, it turns out, is repugnant: He refers to the Latinx students as “taco meat,” barks at them to speak English, and makes crass “build the wall” jokes. Issa’s co-worker, Frieda (Lisa Joyce), is repulsed (so much so that she has to go home and stress-watch 13th), whereas Issa has a more passive attitude toward the man, who, despite his not-so-subtle racism, is boosting attendance. It’s in this instance that Issa rests on the detrimental sort of thinking that favors acquiescence over change, rattling off excuses like “We can’t change him” and “He is who he is.”
It’s only in relation to her love life that Issa seems to undergo a significant transformation. Not unlike Lawrence, she makes some sudden changes to her life, albeit ones that seem like a step backward compared to her now-definite ex. Throughout most of “Hella Questions,” Issa obsesses over things she cannot change: she seeks out a definitive answer from Lawrence, who’s in no hurry to hash things out with the woman who cheated on him; and upon learning that Lawrence is seeing someone, Issa embarks on a nonstop perusal of Tasha’s Instagram, Facebook, and even LinkedIn account (her virtuous assertion that “it’s petty to judge” her ex’s new squeeze is quickly reversed in a spirited bathroom-mirror rap). It’s only when Issa receives verbal confirmation that it’s over between her and Lawrence—closure, it should be mentioned, that’s only afforded when Molly steps in to ask him in person—that she can drop the obsessive behavior (and some light stalking) and make some seemingly small yet significant changes.
Set to SZA’s silky “Supermodel,” the final scene shows Issa finally transferring some of her clothes into Lawrence’s former closet and moving her pillow into the middle of the bed—minor alterations that Issa previously lacked the courage to make. As Issa engages with a Tinder suitor, SZA’s lyrics are eerily apt: “Wish I was comfortable just with myself.” Though it’s hard to view the final moment of the episode—Issa’s Tinder message that reads “Tryna fuck?”—as a particularly happy ending, it is, in a way, a positive step forward for her; in its gloriously grimy Tinder vernacular, the moment is a rejection of magical thinking. It rings in the introduction of a newly single, headstrong Issa.
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