The Insecure Finale Has Us In Our Feelings About Issa’s Choice, Okay?!

For five seasons, we’ve watched Issa Dee (Issa Rae), our homegirl in our head who has always been a bit too insecure to figure her shit out, and Lawrence Walker (Jay Ellis), an aloof former wasteman who seems to be trying his best to be a good man, break up, get back together, and break up again. If you’re a fan of Insecure — whether you’re Lawrence Hive or not — you know that these two have always been the central will-they-or-won’t-they romance of the show. So one of the biggest questions leading into Sunday’s series finale was who Issa would end up with, if anyone, and how her relationship with Lawrence would play out. Well, we finally have our answer. 

Major spoilers for the season 5 finale of Insecure ahead. 

There was a Daniel (Y’lan Noel), a Nathan (Kendrick Sampson), a Condola (Christina Elmore), a whole baby, and some insignificant hookups along the way, but Issa and Lawrence found their way back to each other — for good. For good? We usually reserve this column to look back at some of the most memorable scenes in the best onscreen Black love stories to see if all these years later, they hold up. Here, we’re making an exception to dive deep into a scene that just happened, and to take stock of a couple who may not officially count as Black love canon yet (an honour that comes with time), but this finale is an instant classic, so we’ve decided to treat it as such. 

The thing about Insecure that makes it so great is not just its exceptional storytelling, its characters who feel like friends, or its groundbreaking portrayal of Black ordinary-ness, it’s that every choice the show makes turns into a cultural moment aka Twitter discourse. The debate over whether Issa should have moved on from Nathan and chose Lawrence (or anyone) is raging, wreaking havoc on our timelines and leaving us wondering: would we really want a love like Issa ends up with? Does Lawrence even deserve our girl? And did the final moments of this love story, and the entire series, live up to the expectations we’ve had for the past five years of loving this show? We sort through our FEELINGS (we’re still hella emotional, okay!?) to answer all that and more. One thing is for sure, we’re going to miss Insecure like Tiffany in Denver misses Los Angeles. 

More than halfway through Insecure’s series finale, Issa and Lawrence’s fate is still unclear. After Lawrence’s well-meaning but fully-embarrassing public declaration at Tiffany and Derek’s goodbye party goes left, Issa’s relationship with Nathan becomes a casualty of Lawrence’s outburst, leaving her heartbroken and confused about her next steps. But time (and the support of her besties) heals all wounds — for the most part. Pushing past the split from Nathan, Issa throws herself into her work, devoting her time and energy to making sure that at least the professional part of her life is less… insecure. However, it doesn’t take long before Issa decides she wants that old thing (read: Lawrence) back.

The former lovers meet up at Issa’s new unfurnished office, and the romantic tension between them is thick, as usual. Issa tells Lawrence about her journey to building her dream, and her new digs, but they both know that Issa’s not just talking about work. 

“I keep thinking about all it took to get here,” Issa begins her speech, which is the Insecure equivalent of the epic monologue/declaration of love at the end of every rom-com. “Doubting myself, going back and forth on what I wanted, being scared to waste my time and look stupid in case none of it worked out. And then I realized it was all in my head.” Everything Issa is describing is about them and her fear surrounding their ability to have a healthy, happy relationship. “I had to believe that it would work out for it to work,” she says. When Lawrence asks whether she now believes things will work out, Issa gives the simplest, most honest answer she can: “I’m OK with finding out.” Visibly moved, Lawrence closes the gap between them and takes her into a passionate kiss.

Kathleen Newman-Bremang: The grand gesture here is Issa’s speech, and I guess Lawrence’s declaration at the party. You know I am not Lawrence Hive — for many seasons I have not been able to stand this man — but I love a good romantic speech, and I thought Issa gave a really good speech. I don’t love that it wasn’t Lawrence putting his heart on the line and throwing the hail mary at Issa, instead of the other way around. Think about the penultimate episode when Lawrence’s friend Chad was like, "Yo, you never fight for anything in your f*cking life. Fight for this." (I’m paraphrasing). Aside from declaring his love in the middle of a f*cking party while her boyfriend (Nathan) was there, he didn’t fight. And now, in this grand moment, it’s Issa who is the one that's being like, “OK, let's do this," and Lawrence just gets to be there and accept it. I like it as a gesture for Issa, but I don't like that Issa's the one making the gesture, especially in this relationship, because Lawrence has done nothing, and continues to do nothing, to make this relationship work. Like Chad said, Lawrence just lets life happen to him “like he’s on the dock of the bay.” Not to agree with the goofiest character on the show, but Chad’s right. And Lawrence is doing the exact same thing here.

Ineye Komonibo: You know I’m Lawrence Hive through and through, so I gotta start by saying that I am so happy! My spirit was telling me that it wasn't going to end the way that I wanted, but God had a plan. There is a sermon somewhere in this ending, just for me. I love it! To defend Lawrence, he did try to fight for her. Very belatedly, but he did! Yes, the timing of the moment at Tiffany and Derek’s was very bad, I will give you that, but leading up to the party, they’d been playing phone tag. Lawrence didn’t know if she's happy in her relationship, and Issa assumed that he was still with Condola. He was thinking, this is the only time where I'm going to see this person to say this thing. 

I liked the grand gesture in the office because it’s Issa taking her agency in her love life, and I don't know that she's been able to do that with confidence before. It’s Issa driving the boat, saying, “I'm just going to shoot my shot in the fullest way possible, and you can take it however you want to.” You have to do your part before leaving it up to the universe, so I applauded her for being vulnerable enough to do that and finally say what was in her heart. I thought it was really moving to see Issa be that honest and brave. 

IK: Absolutely not. Whether it's because of his mental health issues, or if that’s just his character, Nathan is a flight risk, and he himself has acknowledged that. This is not the person that you put roots down with or the type to stay and fight for you. Nathan is, unfortunately, a fair-weather boyfriend; when things are getting hard, when they're getting complicated, he dips. With Issa, there’ll always be chaos and mess because that’s kinda who she is. There's always going to be drama around her, so she needs to be with a person who is okay with a little turbulence every now and then (or like, every day). He's too rigid to be that person for Issa. 

KNB: First of all, Nathan is fine as hell. The Lord did well when Kendrick Sampson was made. Damn. We saw that booty last episode. Whew. Anyway, I agree that Nathan never had a shot. Aside from the fact that they have been writing Lawrence and Issa as the One True Pairing (OTP) of the show since the beginning, Nathan was just never the right fit. The way Nathan reacts in any situation when shit gets hard, or tough, or uncomfortable is horrible. He never reacts in a mature or measured way. Every single time something chaotic happens — and you're right, it's Issa, so something chaotic is always going to happen — he either runs, shuts down communication wise, or picks a fight. There's never a moment where he's understanding. He expects that empathy and grace for some of his actions because he’s bipolar, and he’s been open about that. But then, as soon as someone else does something messy or that you could attribute to what they're going through mentally, like when Issa was crying on the man's shoulder, he has no empathy.

The biggest moment when I realized that Nathan never had a shot was in the flash forwards, when Issa was imagining her different future life paths. She’s dreaming about her career and in each sequence, she comes home to Nathan and in each one, I was thinking, Would this man really be okay with her being this successful? Would this man really be okay with her traveling so much and then coming home to him, and still being that supportive? That means that everything they've told us about Nathan is that he wouldn't be. So it was clear to me that this man does not fit into Issa’s future, because the future is her ascending, and Nathan will always stay static. I actually think that’s good for him and his mental health; he needs stability, to be in one place. He needs to do the same thing every day, but that's not what Issa needs. Plus, it’s always felt like Nathan has really liked Issa, but I don't know if he ever really loved Issa, because of the way that he treated her.

IK: Because of his situation, Nathan is also so used to walking away from people and coming back when he's ready. I think men in general have that problem of thinking time is an apology, but where’s the remorse? Where’s the changed behaviour? Nathan suffers from that mentality; he thinks the world runs on his time, but he doesn’t get that he also needs to reciprocate the grace he’s demanding from people. Yes, he is fine, but Nathan just isn’t the one. It was never meant to be.

KNB: He was just not Issa’s man. He’s a good time, not a long time. 

KNB: Damn, that was a good kiss. I was actually impressed because aside from “Low Key Happy” — one of the most romantic episodes in television history — the chemistry between Issa and Lawrence hasn't been giving what it should give. So I was surprised by this kiss because the chemistry was there. I was like, "Damn, Jay! You got all that in you?" I was not expecting to be as turned on by Jay Ellis during that kiss as I was. Listen, Issa turns me on all the time. Jay, he's a very handsome man, but he's usually not giving me the sexy leading man passion that I need. But in this kiss, it was there. It was there for the whole scene. As Issa is doing her speech, it was even in the way he was looking at her. As soon as he walked in the room I was like, "Oh, they're going to make out." I knew these motherf*ckers were getting back together. Because he's just locked in on her the whole time and he's licking his lips. He's walking closer to her while she's saying her lines and shit. I was like, "Damn! He's on one." I was feeling things.

IK: It's a 10 out of 10 for me! Let me say this about Jay Ellis: I am the president of his fan club for a reason. The man has a shine about him. There's a literal sparkle in his eyes! Their kiss felt like an “I’ve been waiting to do that for years" type of kiss. I actually think that they have good chemistry in general. For me, Issa and Lawrence have always been a match. They're like two puzzle pieces that just fit together. When she's doing her usual chaotic thing of going on a tangent because she's nervous, the man is just smiling at her and thinking, That's my girl. In that moment, he’s clearly relieved and thrilled to be there, and he is so excited for their future. You can tell that Lawrence adores Issa and is like, "I'm so happy that we're doing this. Thank God we’re finally here." These people are in love. It's love, man! I don't know what to tell y'all.

KNB: I don't give Lawrence a lot because I think that he has done so many things, to me, that are unforgivable, but I will give him this kiss. 

IK: I think that the right thing, the socially acceptable thing to say is no. But it's a 50/50 split for me. In real life — and God is probably laughing at me as I say this, but please! — I cannot be with somebody who has had a kid with somebody else. I'm just not interested in being anyone's stepmother. My heart's not big enough to do that. However, not everybody feels or thinks that way. Like Tiffany says, “Just because it's not right to other people, or doesn't make sense to other people, that doesn't mean that it's not for you.” And that applies to so much  in Issa’s life. Her career choice may not make sense to a lot of people, and it wasn’t the path that she planned for herself, but it was what was right for her. What I really like about this love story is two people saying, "Okay, our lives are turning out in ways that we did not imagine, but we’re still choosing to come together and create a new life and a new vision for ourselves.” So while I don’t think I would fully want this love, I do love this for them. 

KNB: I would not want a love like this because there is too much water under the bridge. As much as I do believe that Issa and Lawrence love each other, and are in love with each other, I think if either one of them had that feeling with anybody else, they would be with someone else. I do believe you can have that deep love feeling with more than one person. So, if either Issa or Lawrence had that feeling with anyone else, they wouldn't be with each other. The only reason they're with each other, I think, is because they just are chasing this feeling that they've only had with each other. 

I don't believe that Lawrence fully trusts Issa, or ever will. And I think that Issa is going to have to constantly compromise because she's made this decision. I think she’s going to constantly be apologizing for Lawrence and his bullshit, and we know Lawrence is going to come with some bullshit, because he's been doing it for five seasons. He’s going to drop the ball, get complacent, give up on the effort that you need to maintain a relationship. Lawrence has done it all before. I think that the only difference this time is that Issa will be like, "Okay, I'll compromise. I'll take it." She'll be giving away parts of herself in order to make this thing work just because she’s had this connection, this feeling with this guy for so long. I think that she's come closest, probably, to having that spark with Daniel. 

IK: Listen, if Daniel was in the picture, I might have a different answer. If Daniel was still in the equation, I probably would never open my mouth to talk about Lawrence again. But that's why the writer’s room couldn’t go that route — they knew we needed an OTP.

KNB: Exactly. Is this OTP what I would have wanted for Issa? No. I would like a third option. I would like her to have moved on from Nathan, to move on from Lawrence, even from Daniel; Daniel just wasn’t as obsessed with her as a man should be with a woman he’s dating. I wouldn’t have chosen any of them for Issa, but we don't get to choose our friend's partners. I don't get to choose Issa's partner. She's very happy. It couldn't be me, but I'm happy for her.

KNB: To start this off, we've got to note that there's a ring. At the end of the episode, Issa is looking at herself in the mirror and we notice a ring on that finger. She says to Molly about marriage, "Oh, is that what I have to look forward to?" So, the assumption is that she and Lawrence got engaged. Do they stay together? 

IK: They have a long road ahead of them, and it will be a road paved with blood, sweat, and tears. But I do think that in Lawrence, Issa has a real partner. It's not going to be easy…things with Condola are going to get weird at some point. Baby mama stuff is always going to be awkward, and there’s always going to be some drama. But they can approach the problems now with the mindset of, "Listen, we’ve already been through so much. If we want this to work, we need to be serious about it." The stakes are higher because they've already been through the mud, so they have to put in effort to make the relationship better than it was before. So yeah, the engagement is going to last. I think they're going to get married and maybe give Elijah some siblings. And at some point, maybe Condola gets married to somebody else, and then they're all co-parenting. I see it.

KNB: Issa and I are the same person in my brain. I know so many of us think that, but me and Issa are the same. I need somebody who can make a motherf*cking decision and fight for things, because I'm the wishy-washy chaotic person in the relationship. When my husband and I broke up for four days a few years ago, he was the one on my doorstep, crying his face off being like, "No. Let’s work on this." He's that guy. I need that person. I need a grownup in the room. I think that Issa needs a grownup in the room. And the beautiful thing that happened by the end of the series is that she became her own grownup. That’s something I'm still working on. She became the decisive one who will fight for them and that's why she and Lawrence might actually work. I've never liked him for her because I always thought that she needs somebody who's sturdier and takes more initiative in the relationship. Two chaotic people make the mess that we’ve seen for five seasons. 

But I'm going to say yes they are still together for the sake of Issa Dee, because I love her that much. I want her to get her happily-ever-after. We so rarely get to see Black characters ride off into the sunset and get their happily ever after, so I'm going to give this to them. Again, as much as I dislike Lawrence, I knew this was inevitable. Lawrence has always been the endgame. As Issa Dee's best friend (Molly, step aside), I'm always going to think that her husband is trash. But I am still rooting for them, and I think they’ll stay together, mainly because, like I said, Issa is deciding to give up parts of herself, and to compromise, to bend to the whims of this waste man. Forever. 

IK: I get it, man. I get the Lawrence hate. I was there hating with y’all, but I saw the vision. I understand why they're OTP, and I'm so happy it turned out like this! Thank God she didn't end up alone. How sad would that have been after five seasons of mess?

KNB: Being single is totally fine, and lots of people do it and love that life, so I understand the people who wanted her to end up alone and just happy in her career. But Issa has never been that person who wants to be single. Issa has always wanted a partner, and she's always wanted it to be Lawrence, if we're being honest. And I like that Issa ended up with somebody who's wrong for her. I don't think they're right for each other. But that’s life. If you look at most marriages, or pairings, even people that will stay together until they're dead, were they really the perfect match for each other? No. Do their jobs align? Do their personalities match perfectly? No. Life is about just being with the person that you want to be around the most. I do think that Issa and Lawrence like to be around each other a lot, which is…nice.

IK: I won! Lawrence Hive, we really won!