This is it, the bittersweet ending of another season of HBO’s Insecure. And it has me — and the rest of Black twitter — feeling some type of way. What I can saw for sure is that this season has been excellent and I’m angry that it’s going to take them another year to do it again. But without further ado…
Gentrification is real and Issa (Issa Rae) is watching it happen. To set the tone for the episode, Issa walks down the street in her neighborhood and gets offered a voucher for a free cold brew. A new cafe is trying to drum up business. Most of the other storefronts on the block are for sale, and the chipper barista on sidewalk duty happily informs her that the block is being turned into a promenade. Now we know why her rent was suddenly increased.
The rest of the episode takes us through 30 days with Lawrence (Jay Ellis), Molly (Yvonne Orji), and Issa before bringing us to the present and sending us off with our emotions. The perspectives of each of these characters is documented on overlapping days. Things move pretty quickly, with a bunch of short scenes that string everything together. Try to keep up. Let’s start with Lawrence.
Things wit Aparna (Jasmine Kaur) are clearly going well. They run a marathon with some of their coworkers where Lawrence sees Issa and Molly on the sidelines. This only makes him run faster. But it doesn’t stop him from getting closer with Aparna. They are spending a lot fo time together and she even convinces him to get in on a new app called Saddle, since Woot Woot was a dud. Lawrence doesn’t like that Aparna has slept with one of their other co-workers, Collin. Their friendly conversation at the office makes Lawrence uncomfortable and both Derek (Wade Allain-Marcus) and Chad (Neil Brown Jr.) advise him that Aparna having a work boo is a bad idea. While watching their beloved show “Due North,” Derek also mentions Issa, which strikes a nerve. Lawrence is clearly being haunted by the ghost of ex’s past. But instead of dealing with those unresolved feelings, he takes them out on Aparna. As they drive, Lawrence is irritable and accuses Aparna of being dishonest about Collin. She isn’t, and the fact that texting her sister set him off about it is a huge red flag for her. As they argue about it, Issa calls. He doesn’t answer but the proverbial camel’s back has been broken, and Aparna storms out of the car. Another one bites the dust. The next day, Lawrence walks to the door of Issa’s apartment.
Now it’s Molly’s turn. She and Issa are on the sidelines of the marathon to support Kelli (Natasha Rothwell). Molly takes this as an opportunity to talk through her feelings about Quentin (Lil Rel Howery) and his romantic interest in her. Molly is also interviewing with other firms, fed up with being undervalued at her current job. She takes Quentin out for drinks to celebrate her strategic move, except she makes it a point to call him homie. Just when I’m ready to be frustrated with her, she is in her therapist’s office. Both me and the therapist are glad she’s back. Molly’s hang up with Quentin is that he doesn’t seem like the kind of guy she “should” be dating. ‘Should’ is a problem area for her. Just as their session is wrapping, Dro (Saruna J. Jackson) hits Molly with the “I miss you” text, which has been scientifically proven to weaken the resolve of even the strongest women. But one night while Quentin and Molly are working late for a case, she goes for it and sleeps with him! Yasss! Debriefing the encounter with and Issa and Kelli, she commits to just letting things with Quentin “play out” and with several offers on the table she isn’t any closer to making a decision about work. But I think her firm makes one for her. They find out she has been interviewing and to show her their appreciation, they give her a rising star award. In case you were wondering, it doesn’t come with a raise.
Last, but certainly not least, there’s Issa. At the marathon, she and Molly find Kelli at the finish line on a stretcher. She’s ok, but she got her period in the all white outfit and couldn’t finish the race. Also, Tiffany (Amanda Seales) and Derek are having a baby. The mom to be is super happy about her new beginnings and tries to spread the good vibes around to her friends with compliments. She’s having a baby. Kelli is getting fit. Molly is interviewing. Issa is… moving. Ok so maybe she is last and least. Things aren’t going well at We Got Yall, either. She has invited the Latino students to the office for tutoring since the program is full at East 41st Street high School. She finally confesses to her boss Joanne (Catherine Curtin) what has been going on and she is in hot water when she realizes that the organization can be sued for segregation and discrimination. But she does make amends with Frieda (Lisa Joyce), who gets promoted. Later, after “Due North” ends, Issa asks Molly and Kelli to help her pack. Kelli suggests that Issa get a roommate since she can no longer afford to live alone. She plans on living with her brother, who is already being a petty queen with too many ground rules. But first, to drum up some extra cash, Issa has a yard sale. However, she can’t bring herself to sell the couch that was such an important part of her and Lawrence’s relationship. She leaves him a message telling him what time he can pick it up to avoid seeing her, but when she shows up to drop off her keys, he’s still there. It’s the moment of truth.
In Issa’s empty apartment, Lawrence and Issa have what feels like their first adult conversation ever. It’s necessary and heartbreaking. It goes like this this: Lawrence doesn’t like the way they ended things and he feels like he’s “fucking everything up right now,” which he is, to be honest. He apologizes for not being the person that Issa expected him to be. But more importantly, he apologizes for not being the person he expected himself to be, which caused him to shut down. Issa apologizes for not being better, for both of them. She couldn’t even do it for herself, she says. She recognizes that cheating was the “worst” thing she could have done but that she still wants the best for him. She still loves him. He still loves her. We’ve all known that much to be true all along.
But still, what they had together is dead. After they hug it out through tears, it’s time to say goodbye. Standing in the doorway, Lawrence says it first. And then suddenly, the life she will never have flashes before her eyes. Lawrence drops to one knee and proposes. They fall onto their blue couch as a married couple. They have the best sex they’ve ever had and have the cutest little Black baby. It’s too corny to be real. And it’s not. Issa snaps back to reality and says goodbye.
In the aftermath, Molly and Issa have a moroccan themed night at her apartment since they can’t afford to take that trip to Morocco — at least one of them can’t. After all is said and done, their friendship is the pillar of Issa’s life that stands strong. Molly even offers to let Issa move in, since her brother has too many rules. But Issa has already made other arrangements. On her way to the new place that she is going to call home, she gets a friend request from Lawrence. She’s glad that they are finally on good terms. While Molly is trying to find the perfect lingerie… for Dro, who shows up at her door looking like a snack. Issa shows up at someone’s door, too. It’s Daniel’s (Y’lan Noel). “I’m sleeping on the couch,” she says.