Warning: Spoilers for Insecure season 2 lie ahead. If you're not caught up yet, get out while you can.
Somehow, some way, we've already reached the end of Insecure season 2. It was a mess almost from jump, with Issa and Lawrence leaping into bed with other people in failed attempts to get over one another, and Molly making questionable life choices to combat her loneliness.
To refresh your memory, the penultimate episode featured a wild dinner party that forced Issa and Lawrence to have an intense face-to-face conversation; the intimate setting also put things into perspective for Molly, who finally got a chance to see her part-time lover Dro interact with his wife Candice in real time.
In the finale of this season, we linked up with Lawrence, Molly and Issa one month after the last episode ended. Based on how things wrapped up for everyone, we have a few burning questions: is this the real end for Lawrence and Issa? Will Molly ever stop being a hopeless mess when it comes to relationships? Plus, what issues were Tiffany and Derek having earlier this season—and will they surface in season 3?
The finale starts with Lawrence, who's running a marathon with his coworkers—including kind-of girlfriend/friend with benefits, Aparna. Their situationship seems to be on the up-and-up, as we see the two spending time together in various settings. While Lawrence and Aparna are at dinner one night, it comes up that Aparna has slept with another coworker, named Colin. Aparna explains that it happened more than once, but she insists it's nothing serious.
It doesn't take long for the audience to get the sense that Lawrence is feeling—altogether now—HELLA INSECURE. Lawrence addresses said insecurities with his boys, Derek and Chad, who convince him that he has to shut down Aparna's relationship with Colin, because #masculinitysofragile. The next time we see Lawrence with Aparna, they're riding in a car on their way to the movies, and she's laughing at her phone. Lawrence's jealousy starts creeping in, and he assumes it's Colin so he tries to call her out. But she quickly shuts him down, saying, first of all, it's her sister, and second of all, there's nothing Lawrence needs to be curious about; her situation with Colin isn't a thing. Lawrence then makes a fucking rookie move and says, "I just don't like liars," to which Aparna rightfully says, "Wowwww." After briefly shitting on him, she asks Lawrence to pull over—at the exact moment Issa calls, reiterating the tangled nature of their relationship. The timing of the situation couldn't be worse for Lawrence, but it's probably for the best because it gives Aparna a way out of a shitty situation, and it forces Lawrence to face his relationship issues head on. That's the last time we see them together.
Lawrence's featured section ends with him entering the Dunes again, making his way back to the place where it all started.
Molly is attending the marathon that Lawrence and his coworkers are running, alongside Issa. They're there to support Kelly. While looking for her, Molly tells Issa about Quentin, played by comedian Lil Rel. Quentin has made it clear that he thinks Molly is attractive and a badass woman overall, but she thinks he belongs in the friend zone.
In the next scene, Molly is interviewing with another firm, in search of the paper her current company isn't giving her. She and Quentin are hanging out while he's in town, and he hits on Molly again, calling her beautiful but ultimately making her feel uncomfortable. She calls him "homie" in a very obvious attempt to neutralize the situation, and it looks like Quentin gets the hint.
We next see Molly interacting with her therapist, which is a huge improvement from the cold way she approached the sessions in the beginning. Molly's therapist notices Molly is still living in terms of what she should be doing, so she gives her some sound advice: "Get out of the should and live in the could." Right then, Dro texts Molly saying, "I miss you."
After this exchange (or lack thereof), Molly is drinking Henny straight with Quentin in Chicago. Quentin reveals it's the best time he's had working late in the office, which prompts Molly to go ahead and put it on him—despite telling Issa and her therapist that she's just not that into him.
Another conversation Molly has with her girls revolves around her career: she's trying to figure out if she should stay with "the whites" who don't appreciate her, or jump ship to "the blacks," who will. After kicking the decision around, it seems as though she still doesn't have a definitive answer. The next time she's in the office, Molly has a sit-down with her bosses, who are upfront about the fact that they know she's shopping around. In an effort to convince her to stay, Molly's bosses give her the Rising Star award, which is clearly not what she's looking for.
At the end of the episode, we see Molly deciding which sexy lingerie she's about to put on. She opens the door, and we see it's all for Dro. Meaning, Molly has wandered her lonely way back into his arms, after telling him she "can't do this anymore" in the previous episode. So where exactly does Molly see this going? Has she even talked to Candice yet? Or is she still freaking on the side? Given Molly's history, literally since season 1, episode 1, has been about her not feeling like she's enough, this is the worst decision she could make for herself. She's cutting herself in half just to get a taste of what she thinks she wants, and it's not going to be easy to put herself back together. But we'll see where Molly and Dro pick up next season. Hell, maybe they'll have a threesome with Candice.
We're back at the marathon for Issa's portion of the episode. It's here that it's explicitly revealed that Tiffany and Derek are pregnant. Tiffany deems Kelli as "Auntie," and goes on to compliment her for working on her fitness, Molly for taking her career seriously, and... nothing for Issa. After an awkward moment, Issa says she does have news: she's moving. (At the beginning of the episode, we saw Issa walking through her neighborhood, which is quickly gentrifying. As a result, Issa's rent has gone up.)
At work, Issa is talking to her boss about why We Got Y'all is having extra tutoring sessions off school campus. Issa finally has to own up to her going along with the racist vice principal, who was intentionally keeping Latino students out of the program. Issa's boss is understandably livid, as this effectively means that We Got Y'all is hosting segregated tutoring sessions. Issa is in a world of fucking trouble, and Freida, who gets promoted to new director of student outreach, was right all along.
Back at Issa's, Molly and Kelli are trying to get Issa to understand that she might not be able to live alone with her current salary. It's revealed shortly after that Issa will have to move in with her brother, who is very clearly not happy to host his sister.
Neighbor Bae makes an appearance at Issa's yard sale, and they have a friendly, but platonic conversation. Based on this interaction, and the lack of sex scenes for Issa this episode, it appears her "ho-tation" has slowed down considerably.
At the end of Issa's portion of the episode, she arrives at the Dunes to do a final walkthrough before turning over the keys to her landlord. She enters her old apartment and is surprised to find Lawrence. The last time they saw each other was a month prior, at the very awkward dinner party that blew up into a long-delayed confrontation.
Lawrence and Issa are surprisingly brutally honest with themselves, and each other. This might actually be the first time that they've both said everything they had on their minds. Lawrence first apologizes to Issa for retreating into himself during his lows instead of being vocal: "I've been thinking about how sometimes I set these expectations for myself and I just shut down if they don't go how I... I'm sorry for not being who you expected me to be. Who I expected me to be." In response, Issa apologizes again for cheating on him with Daniel: "What I did was the worst thing I could've ever done to you. And I wish I could somehow convince you that it wasn't about you."
They end up admitting that they still love each other, and hug. Before Lawrence leaves, Issa daydreams of their future together, which includes a wedding and a whole baby. She eventually snaps back to reality and watches Lawrence walk away.
Molly and Issa are then seen having a Morocco night, where Molly asks Issa if she is sure she doesn't want to move in with her; Issa says no. While in a car heading somewhere, Issa gets a friend request from Lawrence, and she smiles. For context, Issa found out Lawrence had blocked her on social media in the last episode, and she confronted him about it in their argument. It feels like they might finally have closure, but they still love each other. So does this mean they're starting over, or starting anew?
Before we can wrap our heads around their future, Issa arrives at her final destination. We see that she's not staying with her brother anymore, but with Daniel, who is officially the nicest fucking guy in the world. As soon as Daniel opens the door, Issa tells him she'll be sleeping on the couch, to which he responds, "I know."
In the last episode, which was a month ago in Insecure time, they weren't exactly on speaking terms. But apparently, they've spoken enough in the past few weeks for Issa to feel comfortable enough to stay with him while she gets on her feet. We're all adults here, so let's be real: how likely is it that Issa is gonna be sleeping on that couch for long? When she ends up in Daniel's bed, where will they go from there? Since they first kissed, then hooked up last season, they've had some unhealthy boundaries. They need to figure their shit out before it gets even more complicated now that Issa is in Daniel's house.
Tiffany and Derek
Tiffany and Derek are expecting, and they're excited. It's mentioned in passing that they had been consistently trying in the past, but now it finally happened. This is a little suspicious, for a few reasons. First, earlier this season, Tiffany let it slip during a girl's talk that Derek spent part of the previous year living in a hotel while they got over a rough patch. No additional details were given, but it was one of our first and only clues that their seemingly perfect relationship had some cracks in it.
But this gets even more interesting. During the fuck-boy pow wow Derek participated in with Lawrence and Chad, Derek said Tiffany was watching Chad's favorite show Due North at Issa's. But while waiting for the show to start, Kelli gets a text from Tiffany saying she can't make it. So, if Tiffany isn't with Derek, and she's not at Issa's... where is she?
Also during this conversation, Derek mentions that Tiffany had a close work friendship with a man named Fred, which he apparently shut down: "Fred and I had a talk—Fred is gone now. Why? Because I dealt with it." Or did he? This could ultimately mean nothing, but the red flags in this relationship are starting to get a little bit bigger.
My girl Kelli. In the previous episode, it was revealed that Kelli is still keeping her casual bae Sweetie around. Assuming there will be a lapse of time between this season and season 3, I'm almost willing to bet that Sweetie will still be around. Kelli knows what she does and doesn't want, and she makes that most clear in her love life. If she's not into him, she'll keep it pushing.
Hmm... Maybe that's the overall theme here? Maybe everybody just needs to keep it pushing.