'Insecure' Star Issa Rae Talks Season 2 Finale, Tackling the Gender Pay Gap and Season 3

"It just seemed like something that would go through her head at that very moment of being sad to say goodbye," Rae says of the fantasy sequence surprise.
Courtesy of Justina Mintz/HBO

[Warning: This story contains spoilers from Sunday's Insecure season two finale, "Hella Perspective."]

A lot of things changed for the main trio of HBO's Insecure, but then again, a lot of things stayed the same. For Issa, played by series co-creator, star and co-showrunner Issa Rae, that meant missing out on a promotion at her work and moving out of her apartment as prices rose and gentrification hit Inglewood hard. However, her move elicited much-needed heart-to-heart with (a newly single) Lawrence (Jay Ellis) about what went wrong between them. Briefly, that appeared to lead to an engagement, a marriage and a baby before that was revealed to be a fantasy sequence. In reality, Lawrence simply left and Issa made herself at Daniel's doorstop in the show's closing moments.

As much as Molly (Yvonne Orji) tried to change her future – interviewing at other firms and briefly starting a relationship with one of her coworkers – she ended up, at least for the time being, still at the firm and back to seeing Dro (Sarunas J. Jackson).

The day after the finale, Rae, who also co-wrote the episode, spoke with The Hollywood Reporter about whether the door is closed for Issa and Lawrence, Molly's continued work struggles going into season three and the show's big season two move to summer.

The episode itself was a very ambitious one, spanning a very long period of time and showing multiple perspectives. What made you want to try something so different with this episode? what was your goal or hope in spanning over a long period of time and showing all three perspectives?

Given the penultimate episode, we just felt like we let a lot of things come to a head and kind of explode and, given that, we talked in the room about just wanting to have time pass and how time typically is supposed to heal all wounds. Simultaneously just throughout the season, we've also set up this theme of gentrification and things changing, everything changing around Issa within Inglewood and feeling like this character needs to grow and time would help. In addition to that, her feeling is everything is changing around her and kind of forcing her to grow and change and accept this responsibility and really reflect. Not only for her but for the rest of the characters. Lawrence needed time to grow and Molly, of course, needed time to mend from this relationship so we just got really excited about the idea about being able to spend 30 days in the life of each of these characters that we have been following this entire season.

You've played around a lot of time this season, going all the way back to the fourth episode, where everything took place in a single night. What precipitated that in the second season?

Episode four, I think, definitely inspired the last episode. We liked the idea of being able to set everything in a day and, again, spending time with these characters. Also, just in the LA sense of it all, what a typical party day in LA could be for these characters? We're in our second season and we just wanted to explore different ways of telling stories and it just feels like we're so lucky to be able to do that on this show. We didn't want to feel confined to a very specific narrative. We already play with so many things just within Issa's world using her devices, whether it's the mirror or the fantasy sequences or just the raps. We just want to continue to explore different ways to tell these stories in a grounded, realistic ways.

Speaking of fantasy sequences, there was that big fantasy proposal and the flash-forward. what were you trying to achieve with that scene?

This season, Issa's apartment has represented kind of her relationship with Lawrence and just her stagnation and I think for us it was just about showing what she was missing out on in accepting the responsibility and in accepting her culpability in the demise of the relationship. And having that conversation of closure, we just wanted one of those moments where you wonder what could have been had you not made these decisions? Or if you guys were able to have the kind of closure that led to the relationship mending and it just seemed like something that would go through her head at that very moment of being sad to say goodbye but also hoping and wondering, 'what if?' Issa does to tend to live in the what if, that's kind of what led to the destruction of her relationship in the first place, her what if guy. And so, we just thought it'd be a cool moment given that she's leaving this apartment to wonder what they would have shared had she not done what she did.

Why was it important to have that exchange between Issa and Lawrence?

I think it was a very, very helpful conversation. From the very beginning, from the very first scene of the first season, we set up that this is a conversation that Issa wanted to have with Lawrence. Initially, she wanted to be heard and we started off with him saying, "I get what you did what you did," but there was never an understanding from her side of what she did. I think she always defined the demise of their relationship by the act that she did but never really took responsibility for who she was in their relationship and what she contributed outside of the cheating to the demise of the relationship.

What does this mean for them going forward? Is the door closed for them romantically?

I think it was helpful for her to be able to have that conversation to move on and grow. Do I think the door is closed? Yeah, right now. I don't think that they need to be together and they know that and it really just served as an opportunity for them to just be like, 'OK, I don't hate you, I'm not holding onto this.' This needed to happen and it's exciting for them to be able to have that so we can see where they go from there.

Now that Issa and Lawrence are even further removed, is there ever a question in the writers room of how to continue to incorporate Lawrence into the story as you move into season three? What will always keep him in the Insecure loop?

He's connected to the show by just the fact that he will always be a part of her. I think he'll always be connected to her. When I say the door is closed on them temporarily, I think that’s a romantic door, but there are definitely other responsibilities of how they may continue to have a relationship, you never know. We just really love Lawrence as a character and he just gives us insight on a world that we’re not able to necessarily see in other television shows. We definitely talked about how we want to incorporate him in the next season, and without giving away too much, I'm excited to be able to do that.

What was thinking behind having Issa show up at Daniel's doorstep? That was a surprising turn of events.

It was just reflecting on my own life. There are moments that you have where we get the closure that you need or you have the conversation with your best friend and you're like, 'I'm committed to being better, I'm ready, I'm going to make this happen,' and then you re-lapse. Once you're given a hint of an excuse to go back to the familiarity of your old ways, you take it. And it's a moment I've done in my real life where I've literally had the conversation like, "Yeah, girl, we're doing this." Maybe it's exercising, like, "Every day, we're going to eat right," and then there's a social event and I'm like "OK, I'm just gonna fuck up this one time but I'll get back on track." I think there's a way of justifying and we set up early on that she and Daniel have this history. They go through things but they always find their way back to each other, they always bounce back and I think just story-wise and character-wise, we wanted to explore their dynamic. We've only seen Daniel through Issa's lens and this is an opportunity to define what their relationship is and what their friendship is a bit more going into the third season.

Would you say that's the same reason why Molly ends up going back to Dro? What's her reasoning there?

We've been setting up Molly discovering that No 1. She has options. You don't have to have this specific defined path that she set up. The revelation about the truth about her parents' marriage that she's been aspiring to basically her entire life kind of shattered everything that she knew. But in a good way because it showed her, 'OK, everything that should be isn't necessarily what I need to aspire to. I don't need to aspire to the should's and the could's.' And the option of Dro, who also is exploring options within his own marriage, is one thing but she also explored Quentin. We haven't completely written Quentin out of this season at all. I think she thinks, 'Maybe I can still have both in the same way.' Again, this is something we wanted to set up to explore later on. Getting Molly to go with the familiar but also continue to explore what she set up. She's all about, "I don't have to have just one thing, and that's OK," and to see where that will lead her.

What can you say about her work future in season three given everything that happened in the finale?

It's the same thing, where she's been killing it at this job, or so she thought, and we wanted to get her at a place to really question how she was valued at her job. Whether or not she was going to accept that and I think once she put in so much work and so much time at a specific place, she just automatically assumes you're going to be rewarded and valued for what you put in. Like, 'I've been putting in the work so I should be rewarded. I should be making as much money as my white counterpart and I should rise in the ranks.' Having that shattered made her also realize, like, 'I have options and I don't have to stay here.' That's a hard realization to have because you basically have to start over but by the end of the episode, we wanted to let her know that she wasn’t as valued as she thought she was. But again, she does not have to stay there and she just may not.

You talked about pay equality on the show just as it was becoming a big issue in Hollywood. What did it mean to see that conversation larger happening at the same that it was happening on the show and the kind of conversations spawned from the show?

It meant a lot. It was a topic that became very near and dear to my heart in the past couple of years because I became aware of it. I wasn't aware that it was so prevalent in the entire industry, and not just in Hollywood, but in corporate environments too – just everywhere. It's such an archaic issue that needs to be addressed especially considering the tiers of inequality; not only is it women vs. men, it's black women, it's Latino women and the lie of it all. Being able to explore that on the show and have people talk about it, and to address it and to show a potential solution and to have people kind of question their own personal worth at their job – it fit exactly within the vein of our show because we don't necessarily take a side either way. We just present and we let people discuss and just in seeing the response to the story arc has been really satisfying.

Season two of the show was moved up to summer to air with Game of Thrones and Ballers, two of HBO's biggest shows. How do you think the reception to season two versus season one changed because of that? How do you think that helped the show's visibility?

It helped tremendously. I think we saw that just in the ratings and the response and the social media presence. People have constantly come up to me to tell me how such they regret not knowing about the show sooner. Props to HBO for having so much faith in our series to give us more visibility early on. Day two of the writers' room we got a call from our vice president saying, "Hey, how do you guys feel airing with Game of Thrones?" We were like, "Oh, that would be cool." And they were like, "Well, it's in July, so you'd have to come back way sooner."  We were like, "That's too hard." We initially said no at first, like idiots, because we were like we can't do 10 episodes and feel confident in the season that we would present. And then they came back and said, "You should really consider this. It would help." And we realized we'd be stupid not to, so the solution was to cut down to eight episodes to make the deadline. Even that was hard to do, but it was just so, so worth it in terms of having more people discover and enjoy the show.

What discussions have you had about whether the show will stay in the summer next or a season three episode count?

We have had conversations about staying in the summer and that seems likely. And as far as an episode count, we're still discussing it. I personally still really like eight episodes, I think it's a great model but it's something that's still being discussed.

What can you say about your goals or hopes for season three? What are you looking forward to discussing?

I don't know if I want to say just yet. [Co-showrunner] Prentice [Penny] and I usually get together and discuss a bunch of things that we want to explore. Given that we haven't had a chance to talk about it, I don't know that I want to share just yet. I want it to remain a surprise, but know that I'm excited to tackle some very interesting and controversial topics.

You also have a development deal with HBO. What else are you working on?

We're working with a young writer developing this series right now. We've been developing it over the last year and I've very, very excited about it because it's something that hasn't been showcased within the black experience just yet. I, again, can't talk about it completely yet but know were working on actively developing something as we speak.

Insecure returns in 2018 for season three.

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