Issa Rae - Insecure

Warning: This article contains spoilers from the series finale of Insecure.

Insecure's series finale definitely offered an answer to the inherent question of the show's title.

For five seasons, Issa (creator Issa Rae), Molly (Yvonne Orji), and almost every other character has wondered, "Will I be okay?" (Remember how the pilot used Kendrick Lamar's "Alright"?) According to the HBO comedy's last episode, the answer is " least for now."

Picking up where the penultimate episode left off, "Everything Gonna Be, Okay?!" began with Issa and Nathan (Kendrick Sampson) breaking up again before skipping ahead in time and checking in with the characters on their birthdays and other momentous events. In the end, Molly married Taurean (Leonard Robinson) and started working with Kelli (Natasha Rothwell). Meanwhile, Issa's business took off and she got engaged to Lawrence (Jay Ellis). The 41-minute finale ended with Issa and Molly's friendship stronger than ever (they can even joke about "Broken Pussy" now!) and Issa's "Mirror Bitch" nowhere in sight, implying everything was indeed alright for the time being.

After watching the finale, EW hopped on the phone with Rae to discuss everyone's fate, what the episode originally looked like, and more.

yvonne orji and issa rae
Issa Rae and Yvonne Orji on HBO's 'Insecure'
| Credit: HBO

ENTERTAINMENT WEEKLY: When we spoke in October, you told me you rewrote the series finale about two weeks before shooting it because inspiration struck. What did you end changing about the finale?

ISSA RAE: So much, and we were rewriting up until the finale, but I think I had rewritten it maybe a couple weeks before. Initially the finale was mostly set in Morocco. While it was a fun, different episode, it was just not the sendoff I wanted for all of the characters, and for L.A. To have so much of the series finale take place elsewhere in a show where L.A. was such a prominent character didn't feel right, and it was mostly centered just around Issa and Molly. It just wasn't right, and so [I added] the birthdays and traveling. And it took place five years into the future, so we wanted to be able to see what happened in between that time. This birthday device just really excited me as a way to cap what has been a season of growth for these characters, just from the literal device of getting older and growing in that way, and also just how much birthdays have meant to Issa in the show and friendships over time.

Did you always know you wanted Issa and Lawrence to end up together in the end?

Absolutely not, I did not think that they were going to end up together, and I was in the camp of feeling like I didn't want Issa to end up with a man who had his first baby with someone else, because it was so tied to just my own views and as a writer too. Then as I started to become Issa Dee and started to shoot as her and live as her, I found myself wanting him and missing him and wanting that for her. I think we were both simultaneously on a journey to recognize that we could be happy together, and that last monologue that she ends up saying is so true to how I came around on wanting them to be together.

I know a lot of people were very invested in whether Issa would choose Lawrence or Nathan. Was answering that question one of your main priorities with the finale, or did you have another focus while writing the finale?

Definitely Issa and Molly's relationship, to me that was the true love story, and the finale was crafted just about the real life thing of committing to friendships and thinking you'll be friends forever and you'll always have time for each other, and time not being guaranteed, the circumstances of your life not being guaranteed. That was also a part of the birthdays device — just taking from my own life, considering that a lot of my friends are friends that I've had since high school, and having watched us spend every Friday together, to growing up and having obligations and some having families, and really only having birthdays as kind of a guarantee that we'll kick it and hang out, and that being sad, of just like, "Oh man, we used to be thick as thieves," and we never just imagine that these other circumstances and life would not necessarily make us grow apart, but prevent us from spending as much time as we want to together.

There was something sad about Issa and Molly's relationship going through that, and I wanted to tell a story about that, but also showing their growth and showing that through this love story between them, that they have really helped each other to be the women that they're supposed to be, and the women that they are today.

That scene they have at Molly's wedding was genuinely moving. Was it hard figuring out how to convey that sentiment in Molly's dialogue?

No, because it really just came from the heart. That was thematically what we've been exploring all season, is these characters and specifically Molly asking Issa, "Am I going to be okay?" and these characters thematically thinking about like, "Am I going to be okay if this happens? Am I going to be okay with the cards I've been dealt?" Especially coming off of something like last season, where we almost saw their friendship dissolve, for them to bounce back from that and for them to bounce back stronger was so important to me.

That final speech, you've seen them go through so much, and we've watched Issa become a better friend to Molly this entire season. That was also something that we wanted to showcase,  just why they're good friends and why they're good for each other. To have Molly acknowledge to Issa why she's been such a good friend to her felt really heartwarming to me, and for Issa to receive that. Because we've seen Molly be great to Issa, we've seen Issa be extremely selfish, so to have that recognition from Molly just flowed on the page.

jay ellis insecure
Jay Ellis as Lawrence in 'Insecure'
| Credit: HBO

Molly and Taurean's pairing in the season and eventual wedding definitely surprised me. How did you decide to put those characters together?

This is something that we've been building to for a couple of season, and so by the time we got to this season, it was just like we were all on the same page about activating it, and really thought that Taurean made sense for Molly. He's seen every ugly part of her. She came to the law firm, as he says, and she was hated and he strongly disliked her, but Molly's been looking for someone who is, in a sense, on her level, and who understands her work life, and who gets her, and who balances her temperament, and Taurean really stepped up and showed that he is that for her.

In the end, one thing that we knew from jump is that we wanted to have that final moment with Issa and Molly and Molly getting married. We did toy with the idea of, one, not showing who Molly would get married to, but assuming, and also toyed with the idea that Issa was with someone at the wedding, but we wouldn't see who. But I love answers, and I wanted to just not really play coy about any of that, and we just decided like, "Let's reveal where they end up."

After a "Broken Pussy" reference, the show ends with the shot of the empty bathroom mirror as Issa walks away. What made that the perfect final visual?

It's funny, that was something that we were going to do at the end of season 3 when Issa ultimately chooses herself and doesn't choose Nathan, and she chooses to rebuild her apartment. I was like, "Nah, that's more finale s---, like Issa not necessarily needing the mirror anymore. I would love for that to be the final visual that we end this show with," because that is a mark of confidence, of security, is just, "I'm good with where I'm at, I'm good with how and who I am at this moment." It just felt right for Issa to be walking away from the mirror with a smile on her face, and recognizing how far she's come.

The last line we fully hear is Issa saying, "Now you're claiming it, now you think it's funny." Was it hard figuring out what the very last line of the show would be?

It's funny. It wasn't necessarily stressful, but Prentice and I were brainstorming another scene, and he just pitched something about "uhhh broken pussy" [mumbles] ... He did, I think he pitched the actual line of this thing, "I done broke my pussy," and I started dying laughing. I was like, "Oh man, I love that, that should be the last line for sure." It just felt like that's how we meet Issa and Molly, and that moment was almost like the straw that broke the camel's back in their friendship. They came back from it, but that's how we are introduced to the flaws in their relationship and Issa being a bad friend. To be able to laugh about it literally years later is something that we always say, "I can't wait 'til we laugh about this," and that's exactly what they do. It's a sign of the strength of their friendship.

Before the season premiered, [showrunner and finale director] Prentice Penny told me that one of turning points in writing the final season was when the room realized they had to stop thinking about it as "How do we land the plane for all of these characters?" and approach from the perspective of "Where would we like to see them go in an imaginary sixth season." From your perspective, what aspects of the finale were the result of that approach?

In some ways, their lives are just getting started. Issa has this business that is thriving, and she's in this relationship with Lawrence, and who knows whether or not she is helping him raise Elijah, that he's a part of her life. That's not the ending that she imagined, so navigating that is work. Kelli and her new role working alongside a friend [Molly], there story is right there, in addition to navigating a child she never thought that she wanted with a partner that she decided to have a child with. Tiffany [Amanda Seales] is pregnant again, separated from all her friends in Denver. These are stories that we can continue to tell in a sixth season, and that we'd be excited to tell. Actually, not necessarily excited to tell because the story is over [Laughs], but the point is that those are stories that could be told, and I think that that freed us in that way. Of course, Molly, already low key irritated with her husband on her honeymoon, come on, there's so much to tell there. [Laughs]

We saw Dro in the penultimate episode and Frieda pops up in the finale. Was there anyone else you wanted to bring back for the finale season but couldn't for whatever reason?

[In] season 4, I wanted to bring back Daniel [Y'lan Noel], but we've always argued in the room about that. I thought that Issa could have definitely leaned on him for the Block Party help, but obviously that would've potentially gotten in the way of Issa and Lawrence's reunion. Beyond that, I don't think so. We got our little Thug Yoda sighting in the finale, and he's always been a fan favorite. Maybe I'll think of someone else, but for the most part, I think we saw who we wanted to see.

This story has been updated.

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