lowkey reminder

Are the Characters of Insecure Okay?! Going Into Season 5?

Photo: Raymond Liu/HBO

With a new season of Insecure finally upon us after a 16-month hiatus that’s felt more like 16 years, you may be racking your brain trying to remember how much Issa and Molly still like each other, whose man is still in the picture, and whether Kelli is still listening to herself on her own podcast. Fear not — ahead of this Sunday’s season premiere, we’re here to give you the rundown of who’s killing it in life and who’s on the verge of a mental breakdown. And in honor of the episode titles of this season of Issa Rae’s beloved HBO series — “Reunited, Okay?!”, “Growth, Okay?!”, “Pressure, Okay?!”, etc. — we’re giving each character a verdict of “Okay?!” or not so much.


Photo: Merie W. Wallace/HBO

Things were finally falling into place for Issa at the end of season four. She became a successful event planner with the triumph of her block party. Her relationship with Lawrence was so stable, she seriously considered relocating to San Francisco to be with him as he started a new job there. This is the point when the universe said, “We don’t got y’all, and revealed that Lawrence’s ex Condola was pregnant with his baby. However, there’s one silver lining to the entire mess: Season four ended with Molly calling Issa to meet up, and the former best friends warming up to each other again at an Ethiopian restaurant.

Okay?! Work-wise? Yes. Molly-wise? Maybe. Lawrence-wise? No.


Photo: Merie W. Wallace/HBO

Molly, Molly, Molly. The iron-willed attitude that allows her to thrive in the workplace translates to stubbornness and inflexibility in her personal life. As a result, her relationships suffer. At the end of season four, Andrew, tired of always having to accommodate what Molly wants, appears to break up with her (we never see it confirmed, but it’s pretty clear he’s done), and Molly and Issa’s friendship has deteriorated almost beyond repair. While Issa undoubtedly contributed to the fallout, she did make attempts to mend their friendship that Molly was unwilling to reciprocate. However, with Molly finally initiating their reunion at the Ethiopian restaurant, it appears those therapy sessions may have been productive after all.

Okay?! Not at the moment. Change will be difficult, but this might be what she needs.


Photo: Merie W. Wallace/HBO

It seemed like it would be bye-bye for couch potato Lawrence after season one episode one, but Issa’s primary love interest has really pulled his shit together. By the end of season four, Lawrence is fully thriving. He’s secured his new tech job in San Francisco, and his relationship with Issa is going steadier than ever. Unfortunately, this is when Lawrence learns that Condola is pregnant with his child and he’s hella against it. A reluctant soon-to-be father, a girlfriend-versus–baby mama mess, and a move to the new city? Lawrence is in some pretty deep doo-doo.

Okay?! Nah. Lawrence may have his professional life together, but his personal life is in shambles.


Photo: HBO

Season four ends with a search for Tiffany, who disappears after a night out. Derek, friends, and family immediately embark on a citywide hunt, and eventually find her alone in a hotel room because she was so unhappy that she didn’t know what else to do. The episode is a candid look at postpartum depression and the difficulties of new motherhood. It isn’t going to be easy, but those close to Tiffany dropped everything to be there for her, and they’ll definitely do it again.

Okay?! It’s going to be hard, but Tiffany’s got this.


Photo: Merie W. Wallace/HBO

Kelli has been in a bit of a weird spot with her girl gang. She’s feeling overshadowed by her best friend Tiffany’s married life, newborn baby, and mom friends, and she’s caught in between Issa and Molly’s drama. It’s been low-key rough for Kelli, but as the source of the quote “FYI, don’t speed. I got edibles under the seat,” she’s always down for the ride and can be counted on to make a good time of it.

Okay?! Yup. Kelli takes care of herself.


Photo: HBO

Our current public enemy No. 1 is certain about having Lawrence’s baby, and she tells him that he can be as involved as he wants to be as a father. Condola has always been calm, cool, and collected, but the odds are really stacked against her on this one. Lawrence is absolutely not onboard, Issa — basically the reason why Condola and Lawrence broke up in the first place — is still in the picture, and she has Keke Palmer prepared to “beat Condola’s ass real quick.”

Okay?! Not really. If she’s committing to this child, though, she has no choice but to get it together.


Photo: Merie W. Wallace/HBO

When Asian Bae came into the picture, it was exciting to watch Molly potentially find the one and to see an Asian love interest show some vulnerability. After two seasons of their romance, though, the fire between them is burning as bright as a damp matchstick. Having communication issues from the start, Andrew can’t fully articulate his frustration with Molly’s inflexibility, but while their breakup isn’t explicit, it’s clear Andrew is done AF.

Okay?! Pretty much. If they have indeed called it quits, Andrew looks like he’s been ready for a while.


Photo: Merie W. Wallace/HBO

Nathan gave Issa some attitude about her dating Lawrence, but the exes left things on good terms. Now he has a stable job as a barber in L.A. and, oh yeah, still has the hots for Issa. Given the situation with Lawrence, Nathan is in the perfect place to make a comeback; as the saying goes, just because there’s a goalie doesn’t mean you can’t score, especially when the goalie is distracted by a new family. So, Nathan, it might be your time to kick.

Okay?! Oh, yeah. He’s been on the back burner for a sec, but the window of opportunity may be opening.

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Are the Characters of Insecure Okay?! Going Into Season 5?