a long talk

‘It’s Always Been a Show About Growth’

Issa Rae talks through Insecure’s bittersweet finale, the show’s legacy, and her one regret for Issa Dee.

“Issa and me are overlapped circles on a Venn diagram.” Photo: Natalia Mantini/The New York Times/Redux
“Issa and me are overlapped circles on a Venn diagram.” Photo: Natalia Mantini/The New York Times/Redux

The following interview contains spoilers for the series finale of Insecure.

Even for some members of the Insecure writers’ room, the precise emotional turns of the series finale would be a surprise. The creator, star, and ultimate scribe of the show, Issa Rae, found herself writing and rewriting scenes until the day they were shot. Initially, the episode was a girls’ trip to Morocco for Issa and Molly five years into the future; instead, it evolved into a zip through time punctuated by birthdays, weddings, and pregnancy announcements — big life moments encapsulating the nature of friendship in your 30s. “I went on my own journey as I filmed the season and lived as Issa Dee,” says Rae. “And I decided that I wanted a different ending that paid tribute to the season as a whole.” On the phone, we discussed those decisions — pairing Molly with Taurean and Issa with Lawrence — shooting the final, tearful scenes with Yvonne Orji, and the story line Rae wishes she could have explored that she might just have to pursue in another form.

When we spoke at Vulture Festival in L.A. with Yvonne Orji, she said something would happen in the final season that she found very “surprising.” I was curious about what that was.  

I have a guess. 
You have to guess. You have to.

Is it putting Molly together with Taurean
You know, I think we both came around on our love interests this season. She was a bit surprised that she was ending up with Taurean because, on behalf of Molly, she was holding on to some of that Taurean hatred. I think over time, her defenses broke and she was like, Okay. But I don’t know — maybe she didn’t! But I love it. [Laughs.]

How did you and the writers decide to go with Taurean? 
It was something we decided a couple seasons ago — that Molly and Taurean were equally yoked, and he was the person to ultimately understand her. We’ve seen Molly struggle with explaining her career and work obligations to love interests. We’ve seen her be overzealous. He’s such a no-nonsense, balanced person, and to have someone who is equally as ambitious as her and accepts her — and has seen the ugliest parts of her and still wants her — felt really appealing to us. And they have such great chemistry that it felt right.

But tell me, what was Yvonne’s reaction when she first heard that would be the trajectory?
You have to ask her. [Laughs.] It’s very vivid in my mind, but you have to ask her. Pour her a drink and ask.

So you had to come around on Issa and Lawrence, too? 
At the beginning of this season, I was not sold on Issa choosing Lawrence.

Why not?
In Mirror Issa’s words, I thought she was being a dumb bitch. I didn’t think it was gonna work. As the season progressed, I started to unpack what that meant and why they could not work it out if this is what she wanted. And I realized deep down that I did want them to be together. In thinking about the series as a whole, and about the growth that they’ve experienced and the love they do have for each other, and thinking again about my own life, I felt like she would try it out. She would give it a solid chance. This is her person.

What was the lay of the conversation in the writers’ room?
We were pretty split. Everybody had their own ideas. I mean, we all thought of ways it could work and ways it wouldn’t. Some people were very adamant that they should not be together. So it ultimately would have to come down to me, and it really came down to writing the finale. The moment of being with Nathan and thinking about Issa’s future and what it meant for her to be happy, it dawned on me that she really does love and miss Lawrence and had never been able to give it a proper shot. And these were just circumstances that happened — you know, him having a baby with someone else. I think she was right to take a break from him. But if he was down to revisit it and she was single and available, why not try and say that you tried? And if it doesn’t work out, at least you can say you’ve really given it a shot. The last time we saw them give it a shot, they were interrupted. And they were the best versions of each other for that moment, and they’ve only done more growing since then. The romantic in me wanted that for them.

You’re talking about season four, episode eight, when Issa and Lawrence come back together, right? 
Yeah, eight and nine. The brief bliss they shared. And the fact that she was ready to move to San Francisco for him. She was ready to uproot her life. I think everything happens for a reason. And I think if she had moved, the Blocc would’ve never taken off in the way that it did, and she wouldn’t have been able to find her own footing. It was an important decision for her, but for me, it was the least important decision for her to make. Sometimes we put so much weight on these decisions of love interests. That was part of her journey, but it wasn’t her entire journey.

What was the most important decision for her to make? 
From the start, this show has been centered on the story of a girl trying to figure out who she is and where she’s going. The most important choice she’s making is to be happy with who she is and where she’s going. To be secure in what her flaws are. This is a journey of being uncomfortable with the uncertain, and we’re watching her do just that.

How do you relate to that? 
Oh, God. How don’t I?

What is Issa to you? I assume you’re processing things in your life through her.
This season finale, Issa and me are overlapped circles on a Venn diagram. So much of it overlaps with who I am and who I’ve become. The journeys are different, but where we are is very similar. I have had to be confident that things are gonna work out and confident about what I don’t know, who I’m not, and where I’ll never be, but optimistic that things will work out the way they’re supposed to and secure in the fact that I have these insecurities and these flaws, and I have so much more learning to do. I have nothing figured out yet, but I have just enough to be confident where I’m going.

Is it that you get to do it onscreen through a character in some ways? 
[Laughs.] Definitely, definitely that.

What was the reaction like at the table read for the finale?
There were tears. We were all very aware of the fact that this was the last table read we’d ever have together. I remember Yvonne actually crying while reading that final speech Molly gives Issa in the bathroom, and being like, “These are words that I would actually say to you.”

But I remember being like, Uh-uh, I need to rewrite some of the script. Some of this didn’t hit the way I want it to. That conversation between Issa and Nathan changed, and the moment with Issa and Lawrence at the Blocc office did not exist pre-table read. Before, Lawrence just showed up at the wedding.

So you were just gonna raw-dog it.
[Laughs.] I mean, that’s pretty standard for us, so it would’ve been on brand.

Why did you think it was important for them to have that conversation? 
That felt missing in the table read. It was like, And here we are together. And to be fair, that’s kind of what it was in previous drafts, too, because we didn’t wanna focus on them getting back together. But this is a part of her, and this is a part of her journey, and you do feel cheated in not knowing why and how much this relationship means to her.

My understanding is that the finale you shot differed a lot from the original idea. What did you want to do first? 
Initially, we jumped five years into the future and had Issa and Molly reunite in Morocco and told the story of what happened through this adventure — misadventure — in Morocco. And while the episode was funny and exciting and different, it just didn’t pay homage to what — you know, the show is set in L.A., and they went back to L.A. in the last couple of pages. A lot of that montage you see in the finale currently was still there, but setting the show away from L.A. for such a long time felt wrong.

Is that how you came up with the structure of moving through big events like birthdays and weddings?
Birthdays was just the core. I thought about the pilot and even the third season in the show: Birthdays have been such a source of significance for Issa and our characters, and when I think about my own friendships and getting older, birthdays are the only promise we have to hang out. And it is sad when we can’t make that happen. Just as a naïve promise that the girls make to each other, and Issa and Molly in particular, to always be there for each other’s birthday is — it is just that. It’s naïve, and it discounts all the events that can happen in life, and it’s still the one thing you hold on to as the celebration of your friends and the commitment you have to them. We watched them recommit to each other with the hopes of being able to hold on to that but not necessarily counting on the fact that particular events in their lives might keep them from each other. There was something beautiful in following that.

Did you know you wanted Molly and Taurean to get married? 
From breaking the first season and presenting that to HBO, we knew we wanted to be at Molly’s wedding. There was even talk of not seeing it and just focusing on the moment with Issa and Molly in the bathroom post-wedding, committing to each other and thanking each other for being in one another’s lives through all the ups and downs. But I wanted to see Molly get her dream wedding. To see Molly and Taurean just be great together. And to see her surrounded by her friends and family, and obviously reunite the characters for one last time. It was so much fun to shoot, and everybody looked beautiful.

Of course, Molly’s mom passing was another thing that progressed as we were writing. We knew she was having this stroke, but experiencing personally some of the events in friendship with loss, that really hit close to home. I had a couple of friends lose parents, and the friendship in some cases shift — feeling helpless in terms of helping them and seeing the distance grow between us and having to work to close that gap. To see Molly and Issa go through that and overcome that was something that felt representative of things that happen in friendships in your 30s.

How did you come to some of the other big moments like Kelli getting pregnant? 
Kelli had been on this journey throughout the season, just thinking about her legacy and what she wanted to leave behind, and she ultimately found that in the new profession she takes on with Molly: the estate-planning division. She really finds solace in leaving her job behind but also realizes that she wants her own legacy and needs someone she feels is worthwhile of carrying that through. And she has a revelation of her own that she can change her mind. She can decide what’s best for her, and that’s just fine.

I think we can think that we’ve made up our mind about things — I certainly have — and then decide, Oh, wait. Maybe what I thought I knew the entire time wasn’t necessarily true. And I can be fine with just deciding, Never mind.

What was it like shooting that conversation with Yvonne in the bathroom getting out of the wedding dress? 
Ugh, it was devastating. It was Yvonne and Prentice’s last day, and, you know, I’ve been talking a lot of shit the entire season about how more sweet it is than bitter that this show is ending, and I was ready to move on. That day, I had a very early call time. I get picked up by a van every morning, and I was crying in the van on the way to set before we had even started anything. I was like, What the fuck is this? I was bummed about the fact that I wasn’t gonna be seeing them. And then even that first scene with Prentice directing, I started crying with him telling me to, like, move across the room. So when it came to that night, I was like, I have gotten my tears out; I’m gonna be okay for this scene. And Yvonne was fine all day; she was great, and I was like, Maybe I’m tripping. This is a happy day, and Yvonne’s really keeping it together. And then I went into the makeup trailer and I see Yvonne with tons of tissues with our makeup artist. She’s bawling. And I was vindicated, I was like, Aah! You feel it too! And she was like, “Don’t do this right now. Please.” So then when we did the rehearsal, we couldn’t even say the words. Because the words were true about me and Yvonne too. I almost didn’t want to do the rehearsal. You know, let’s save this, but we had to kind of run it. And it was just so somber.

And then during the scene, we do coverage. Yvonne goes first, and I’m all crying during her take. And there’s a point where you’re kind of cried out. And so on my coverage, I was tearful, but I wouldn’t say that it was my best performance. And so Prentice, unbeknownst to me, had Yvonne actually talk to me as Yvonne and say words to me. Yvonne is such a beautiful speaker and such a generous person. Her words really moved me to tears, and so it was not only a moment between Issa and Molly, but me and Yvonne. It just gutted me by the time we yelled “cut.” And that was the very last take, and we came out and said good-bye to everyone.

What did she say?
I’m gonna cry thinking about it. She was basically like, “Thank you for seeing me and for taking a chance on me. You didn’t have to, but you did, and I’m better for it.”

“Ee have shown the beauty and ugliness of relationships, and love in particular, in a way that hasn’t been done in a long time for our story.” Photo: Merie W Wallace

After bell hooks passed, I saw a quote from her book All About Love going around Twitter: “Friendship is the place in which a great majority of us have our first glimpse of redemptive love and caring community. Learning to love in friendships empowers us in ways that enable us to bring this love to other interactions with family or with romantic bonds.” That statement really resonates with the core relationship of Insecure. I know you majored in African American Studies at Stanford, so I was curious to hear how her work influenced you or if you ever got to meet her.
No, I never had the privilege of meeting her, but I studied her work obviously in high school and have looked up to her, have aspired to her. To have her understand and empower the state of Black womanhood, to acknowledge and make it so beautiful and so human, was just a gift. And it’s such a tremendous loss. She felt so fully formed in a way that one can only dream to be. And so raw and honest. I think so much of what we attempt to do is the same. I wouldn’t compare Insecure in any way to the works of bell hooks. [Laughs.] But I think what we do have in common is showcasing our humanity and showcasing our love and normalizing that in a way that people can own. Our people can own. I think that’s what I’m most proud of with the rawness of Issa and Molly’s friendship and the ups and downs and how we have showcased love in this show. If anything, we have shown the beauty and ugliness of relationships, and love in particular, in a way that hasn’t been done in a long time for our story.

Love takes work.
Yes, it does. One of the other things I will say about our show is that a lot of people have projected what they wanted our show to be as a result of it being a Black show. It’s never been a show about four women; it’s never been an arguing show; it’s never been a gender-war show. It’s always been a show about growth. It’s always been a show about this friendship and this central love story between these two women and how they’ve helped each other become who they’re supposed to be.

Episode eight has Issa Dee imagining the paths different decisions might take her down. Are there pivotal decisions you’ve made in the past that you still dwell on? 
Hell. Yes. And they keep me up; they scare the shit out of me. That episode was very close to me. It is one of my favorite episodes because it’s a state I live in. I like to think I’m on the right path, but it’s really terrifying. There are certain fork-in-the-road moments that would’ve altered my life, and I’m happy now, but I could’ve not been. It’s the road less traveled, it’s the path not taken, it’s the what-could’ve-been, the what-if. And from the pilot, Issa lives in the what-if. I live in it less, but there are times when I think, Oh my God, what if I had done that? Or, Oh my God, what if I had been caught doing this? Or, Oh my God, what if I had taken that door? Or left just a second earlier? Where would I have been? Or, Would it have been better? Sometimes I wake up in cold sweats. I know that can be crippling, and I have been way more intentional about living in the present and the now and practicing gratitude for the choices I have made. And recognizing that I have so many more choices to make. Inshallah. [Laughs.]

Can you give me an example?
It’s gonna sound so stupid and Lauren Conrad of The Hills. In college, I got this opportunity to study abroad in Paris, and there was someone I was seeing. I really wanted to go, and I got admitted last minute. And simultaneously, I had a script with a friend that became a semifinalist selection at Sundance, and we would have to be in L.A. if we were selected as finalists. And so I had to choose whether or not to wait. I don’t know why it was so dire, but I had to choose: Do I go to Paris and be with this person and explore this relationship? Or do I stay in L.A. and hopefully I get selected?

I didn’t go to Paris, and we weren’t Sundance finalists. And so I was always like, What the fuck! Stupid-ass decision! What would have been? But ultimately that led to me continuing to create. I ended up taking time off of school, came back harder, created my first web series. And then even the decision to come back to L.A. from New York. I wanted to stay out there and hustle to make things happen, and if I hadn’t come home for a weekend on a whim and gone to the beach with some friends — they were the ones who convinced me to move back. There are so many pivotal moments where I could’ve said yes or no and my life would’ve been drastically different.

How do you know you’re on the right path? 
I’m very in tune with what makes me happy. If I’m not happy, if I’m miserable, or even if I’m feeling doubtful, then it will cause me to take a step back and figure out what it is that I really want. So I am rarely unhappy. I don’t know that I have been unhappy in a very long time even when things aren’t going according to plan. And that’s kind of my barometer.

How do you get in touch with that part of yourself?
I’m not a guru. I don’t know. I’ve never really thought about it or questioned it. And I kinda don’t want to! [Laughs.]

It might be better not to futz with it! 
You know, if it ain’t broke.

Did you know the final scene of the show would be a reference to Issa and Molly’s first conversation about a broken pussy at Merkato in the pilot?  
No. Prentice and I were discussing what they’d be joking about on the phone, and he just pitched that, and it cracked me up. Molly thinks it’s funny now. That’s the growth in their friendship, that they can laugh about what was a truly traumatic moment for Molly and Issa’s friendship. She can own it. And you know, this is the acceptable pussy break. I have a man and a husband that broke my pussy. It’s not a sad broken pussy. It’s a happy broken pussy.

When you shot that call, was someone else reading her lines to you? 
Yo, that’s so funny because normally, there would be a stand-in doing it. And thank goodness, because it was actually Jay Ellis’s last day on set, Yvonne came to send him off. So I did have a stand-in reading with me — and God bless our stand-ins, I love them — but I was like, “This is the last conversation of the episode; I want Yvonne. Please! Is there any way she can come read it?” And she happily did. She was just off-screen talking to me on the phone, and it made a world of a difference.

Did you ever consider bringing back Daniel somehow?
We talked about bringing him back in the final season. There’s about three Daniel lovers in the room, myself included. And the rest of the haters — as I like to call them — shut it down. It didn’t make sense for him to come back. You know, it made more sense for him to come back in season four, which I also advocated for. But everybody doesn’t see it for him. Our resident, like, “Come on, be real for the Black women in L.A.” officer, Amy Aniobi, is just like, “Okay, all the n- - - -s can’t keep coming back to Issa’s life.” Just fine men everywhere who keep coming back? That does not happen. So that shut it down.

Does anything in particular stand out to you from the experience of making the show?
I realize how special my experience has been and how unique it is. And to the point of being on the right path, so many things have to go right, and so many of the right people have to be involved to make this show. Despite my frustration of being in development for such a long time, I think about the show that could’ve been and the show that is. And how much better the show is because of time and what it went through and what I went through. I already miss every part of this show and every part that went into making it happen and truly do feel grateful for the people who’ve been along for the ride. And who actually love these characters. I think if you love these characters, then you’ll feel satisfied by the finale. Hopefully. But, yeah, I’m just — I’m so happy that people are taking this show into their heart.

Do you feel like that long development period was ultimately good then? 
Hell, yes. Because it made me tap deeper into myself. In working with Larry Wilmore early on — that was for the workplace-comedy version of the show — being able to take that and what we discussed and tap into who I was at that time, that was a journey. And so much happened in my own life as I was developing the show, creatively and personally, that helped add to it. Everything happened the way it was supposed to with time.

How do you feel like you’ve changed since starting the show? 
I feel secure. It’s so corny, but I do. Issa Dee has worn her heart on her sleeve in a way that has inspired me. This show has made me more openhearted and less closed off — though you’d have to talk to my friends about how true that is. But to me, it’s made me more vulnerable.

Are there any other plotlines you wish you could have done? 
Yeah, actually. Especially — and since it is so present in my life right now, and I’m curious about it — I do wish we could’ve explored motherhood through Issa. And deciding to or not to. That is something super real that we discussed in the room: Women having this ticking time clock that’s so unfair that men will never experience. They can be like, Yeah, I’m 53, it’s time to have kids. And we really have a time to decide. You can freeze your eggs, you can do all these things, but there’s just something. There was an interesting discussion that happened in the room that men were enlightened by — annoyingly so — that the women in the room really bonded over: Oh my God, you feel this way, too? Even if you don’t want kids, you still feel that clock. And there’s such a pressure in the back of your mind of having to decide. That’s something I wish we were able to explore. Maybe we’ll explore it with something else.

As in a different show?
Maybe. Who knows? Or I’ll explore in real life.

I am exploring in real life. I mean, we’ll see.

‘It’s Always Been a Show About Growth’