Every season of Insecure proves to be even more fraught than the last one. In the HBO gem’s third season alone, Issa Dee (Issa Rae) found herself living with Daniel King (Y'lan Noel), a man with whom she has had an on-again, off-again flirtationship for over a decade. He was also the central figure in Issa’s biggest breakup. And he’s someone she nearly hooked up with, yet again, during their little cohabitation crisis.
Elsewhere in the Insecure universe, Molly Carter (Yvonne Orji), managed to alienate nearly every new person in her life, and Tiffany DuBois (Amanda Seales) seriously hurt her own BFF Kelli’s (Natasha Rothwell) feelings. There was a lot of mess to go around during Insecure's third season.
The season 3 closer wrapped with the traditional post-show “Wine Down” special, starring usual hosts star-creator Issa Rae and Insecure showrunner Prentice Penny, along with Molly’s portrayer Yvonne Orji. As we see in “Ghost-Like,” Rae and Orji’s characters are now poised to seriously pursue romantic relationships with men in the same orbit — roommates Nathan (Kendrick Sampson) and Andrew (Alexander Hodge) — when Insecure returns for its fourth season. Writer Penny pointed out this is new, likely treacherous terrain for HBO’s leading Los Angeles best friends.
“Typically we’ve always had their relationships as ‘Issa’s dating this guy’ and ‘Molly’s dating this guy.’ And never the twain shall sort of meet” showrunner Penny explained, gesturing to show how physically separate both couplings have usually been over the past three seasons. “What’s interesting now, is what will this friendship be like [in a new situation]?”
Immediately, a few problems spring to mind. When best friends start dating roommates, usual fair-game topics of conversation feel tricky. Will Molly be as enthusiastic about Issa getting hers in the bedroom when Molly is the one sitting a few feet from Issa’s partner’s door (and has to hear every sex sound)? Will Issa know what to say — and what not to say — over breakfast to Andrew when Molly isn’t there? Will Issa and Molly be sharing a bedroom wall, or will these two need to create a sleepover schedule to avoid sharing a bedroom wall?
And, as Sesali Bowen brought up during a post-finale debrief, if one of these relationships tanks, will Issa or Molly demand an impossible loyalty pledge from their still booed-up friend? After all, it's not like Issa or Molly can avoid their new bae's roommate, no matter how much their broken-hearted BFF might want them to. Prentice and Rae didn’t discourage the fact this uncomfortable scenario could be ahead, repeatedly saying such a situation is “real life.” Real life drama, as we’ve seen over the last three seasons of Insecure, is precisely what this HBO comedy is going for. There’s no reason to doubt season 4 will be any different.
The imminent train wreck of Issa and Molly’s entangled love life is a far cry from the days when the former was dating Lawrence (Jay Ellis), and the latter was ruining her budding relationship with nice-guy mechanic Jered (Langston Kerman). In fact, the Nathan and Andrew of it all promises to be even more problematic than Molly’s relationship with Dro (Sarunas J. Jackson), a man so close the Insecure group, he was invited to both Derek’s (Wade Allain-Marcus) 30th birthday party and Tiffany’s baby shower. Remember, Dro and Molly even had sex at Derek’s dinner party. Yet, the Issa-Nathan-Molly-Andrew powder keg might be even more explosive.
Or, as Orji remarked during the “Wine Down” special, “This sounds really messy, guys.”
While the post-show chat naturally revolved around Rae and Orji’s characters, there is an Insecure season 3 twist that may create even more chaos next season: the ascendance of Tiffany’s newly introduced friend, Condola (Christina Elmore). Viewers meet Condola during a fairly short scene in “Ready-Like,” which was built around Tiffany’s over-the-top baby shower. In the episode, newbie Condola shares some short flirty banter with Issa’s ex-boyfriend Lawrence.
In finale “Ghost-Like,” it’s confirmed there is more going on between these two than some simple flirting.
Condola and Lawrence have been on multiple dates. Their season-ending meet-up is simply the latest one, and seemingly their most serious, since Lawrence announces he has accepted Condola’s divorcée past. This would be complete good news, if it wasn’t for the Condola scene that comes right before her date. In that moment, it’s revealed Issa is seriously considering working with Condola, an expert at pro-Black cultural events, on the all-Black Inglewood block party our leading lady been striving towards creating for multiple episodes. Of course, Issa has no idea Condola is seeing her most significant ex-boyfriend. It’s totally possible Condola has no idea her prospective new business partner is Lawrence’s most meaningful ex.
So, when Insecure returns, it’s entirely possible Issa will be working on her very personal passion project with Lawrence’s most important love interest since their split.
To quote Yvonne Orji one more time, “This sounds really messy, guys.”
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