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This article contains spoilers for Season 2 of “Insecure.”

When Issa Rae hosts “A Sip,” her live event series, she starts by asking her guests: “What are you toasting to?”

She raises a glass with the person she’s interviewing – always a well-known creative – then takes a shot to kick off their conversation. In March, she spoke to Sean “Diddy” Combs in South Los Angeles.

“We’re gonna toast to how you’ve changed the game and broke down barriers. We just wanna toast to you, Issa.”

His short tribute to Rae captured how fans within the entertainment industry and beyond view the multitalented co-creator of HBO’s “Insecure.” As an actress, writer, producer and entrepreneur, Rae, 33, is a force. The stories she tells on television are uniquely special, in part because of who she is: A dark-skinned woman who grew up in South L.A., Maryland and Senegal, where her father is from, Rae spent time honing her craft with multiple Web series before landing a deal with HBO to create “Insecure.” Within a few years, Rae has become a talent everyone wants to work with: Rappers such as Drake and Jay-Z have asked her to appear in their music videos. In addition to developing two new shows for HBO, Rae stars in the upcoming “The Hate U Give,” a film adaptation of Angie Thomas’s novel, and she just finished filming a movie with “Black-ish” star Marsai Martin.

Issa Rae. (Taylor Jewell/Invision/AP)
Issa Rae. (Taylor Jewell/Invision/AP)

“Insecure,” which premiered its third season Sunday night, highlights young, complex black characters living in South L.A., where the show is filmed. Rae’s character, Issa Dee, is a flawed woman with many strengths — including a knack for freestyle rapping while looking into her bathroom mirror. When Season 3 picks up, Issa is staring into a mirrorless medicine cabinet in Daniel’s (Y’lan Noel) bathroom. It’s indicative of her current life situation: She’s sleeping on Daniel’s couch, where he once gave her an extremely rude “facial” while they were hooking up, because she can’t afford an apartment on her own. (Her credit score is also a cool 425, and she is eating PB&Js and granola bars at restaurants.)

For a split second at the end of last season, “Insecure” writers tricked some viewers into thinking that Issa would end up with Lawrence (Jay Ellis), her former boyfriend whom she cheated on with Daniel. In one of the finale’s final scenes, Lawrence gets down on one knee in the doorway of the apartment they once shared. Then, a gorgeous montage featuring Issa and Lawrence happily doing life together ensues, signaling to viewers that the scene was a mirage. Even Michelle Obama was deceived.

Lawrence (Jay Ellis) and Issa (Issa Rae). (Justina Mintz/HBO)
Lawrence (Jay Ellis) and Issa (Issa Rae). (Justina Mintz/HBO)

On Hot 97’s “Ebro in the Morning” last week, Rae recounted a story she first documented on Instagram after seeing Obama at an event in Boston last year. “She was like, ‘I’m mad at you. … You fooled us,’” Rae recalled. Obama told her she loved the show, and that her daughters, Sasha and Malia, had put her onto it.

Ellis might not return as Lawrence to “Insecure” this season. Exes don’t always remain friends or run into each other, and Rae wants to “stay as true to life as possible.” Season 3 will continue to explore Issa and her best friend Molly’s relationships with themselves, each other, the men in their lives and their careers. Issa is still relegated to desk duty at We Got Y’All. The nonprofit group where she works is dealing with its own internal crisis, and Issa is feeling less connected to its mission. To make extra money, she adopts a side hustle as a Lyft driver. Meanwhile, Molly (Yvonne Orji) struggles to adjust at her new, all-black law firm.

Issa and Molly (Yvonne Orji). (Merie W. Wallace/HBO)
Issa and Molly (Yvonne Orji). (Merie W. Wallace/HBO)

We caught up with Rae the day after the Season 3 premiere aired, which she watched with some “Insecure” cast and crew members at Twitter’s L.A. offices. She dished on “brutally honest” friendships, why fans are so protective of Lawrence, and her ideal party Lyft snacks.

This interview has been edited for length and clarity.

The Lily: I’m going to take a cue from your “A Sip” events. If you were holding a drink right now, around 1 p.m. in L.A., what would you be toasting to?

Issa Rae: Toasting to being able to have the freedom to just create and to be myself.

Issa Rae. (Taylor Jewell/Invision/AP)
Issa Rae. (Taylor Jewell/Invision/AP)

TL: When you’re watching with everyone on Twitter, do you like being able to engage with your fans as the show unfolds?

IR: Oh my God, I love it. In fact, I was low-key irritated that we weren’t watching the live version. It was the HBO Go version, so it wasn’t up to the minute. Usually we go to somebody’s house with cable and then just see what people are saying [on Twitter] as it happens. It’s so much fun to see people’s real-time reactions to moments that we pored over in the writers’ room. Either they love it or they hate it.

TL: Can you talk about the differences you see in your character, Issa, from Season 1 to Season 3?

IR: She’s working on being more honest with herself — or at least trying to be. She’s really understanding a lot of the mistakes that she’s made. Not realizing what she has and who she had. Staying in a bad situation for too long, whether that’s work or relationships. And I mean, kind of lying to yourself is a huge mistake.

We’re aiming to have her realize how selfish she’s been. She’s focusing on what she wants — and what she really wants, not in a superficial way. Who she wants to be and how she wants to be that person.

Issa. (Merie W. Wallace)
Issa. (Merie W. Wallace)

TL: What about yourself? I saw you tweet the other day that you’ve been working on the show for five years. How have you changed personally from when you first started the show to now?

IR: I’m willing to trust my instincts a bit more. I love collaborating, and sometimes in the past, I might doubt myself or defer to someone else’s opinion. I still to a degree do that, but I think I’m gaining more confidence, ironically. Of feeling like, I know the stories I want to tell and the voice I want to tell it in. I just want to tap into more of my experiences.

TL: One thing that I love about Issa and Molly’s friendship is that they’re really open with each other. They tell each other when they disagree with what the other person is doing, but they don’t necessarily get angry in the moment. Do you have that type of relationship with your close friends?

IR: For the most part, my friends and I are able to tell each other how we feel. We have a very brutally honest relationship, which is also couched in our sense of humor. I can tell when my friend is joking … [with] me, but then I can tell when there’s something beneath the joke. There’s always going to be stuff where it’s like, “Oh my God, I already told you this before. You’re never going to get it.” Then you have to decide whether or not it’s worth keeping that friendship. That’s in any relationship.

That’s something Issa and Molly will discover as well: that all relationships are about adjusting, and they can be hard.

TL: Issa is struggling financially even though she has a job. She can’t seem to find an affordable place in Los Angeles, and she’s from there. Is there an underlying message here?

IR: One, L.A. is changing fast. There’s a huge homeless problem here. There’s so much happening. But in this generation, it’s not enough just to have a job. You have to have a hustle. Issa wasn’t financially stable. She got into an accident; she has to fix her car. The gig economy is so necessary. People have student loans. It’s an average person’s problem, but I think she really hit rock bottom in a way because of some of the choices she made, and that’s a real situation I’ve been in — of having multiple jobs. The nonprofit world does not pay well, and for me, it was just about finding other jobs. I was doing videography and editing and trying to do whatever I could to make some extra income, and it still just never felt like enough. I was in a constant pool of debt.

Issa. (Merie W. Wallace)
Issa. (Merie W. Wallace)

TL: During last night’s episode, someone tweeted:

IR: If someone would have told me that a few years ago, I would have easily done that. I was looking to move back to Senegal before “Awkward Black Girl” hit, so I get it.

TL: Would you ever move to Senegal in the future?

IR: I actually don’t know. If this administration stays the way it is or it gets even worse, I would definitely consider it. Senegal is way more peaceful.

TL: The #LawrenceHive is mad. Outside a New York screening of the show, there was this guy screaming, “No Lawrence, no peace!” There’s a petition. It’s comical, but I’m also interested in why you think people, particularly men, have connected with Jay Ellis’s character.

IR: It’s so dope. I joke, and I give #LawrenceHive a hard time. Most of the ones who take it too serious get mad personal, and I’m like, “Calm down.” But as a whole, it’s incredible that so many men — so many black men — have taken to Lawrence’s character. I realized that there just haven’t been regular black dudes on TV. There’s either an aspect of crime, or hypermasculine representation, or something that has to do with sports – but that’s not what all black men are. Not since the ’90s have we really had a representation of a whole, regular black dude.

Lawrence. (Justina Mintz/HBO)
Lawrence. (Justina Mintz/HBO)

So many men identify with a lot of [Lawrence’s] choices and who he is and how he identifies as a nice guy. It’s cool that a show that is primarily run by women can do that. I credit our showrunner, Prentice Penny, who is always like, “This dude has to be a well-rounded character.” Because sometimes women tend to write men who are either super ideal or who ain’t shit. On the show, we’ve always just wanted to show everyone’s flaws.

TL: What about for Daniel? I feel like I haven’t seen the same camaraderie surrounding him online.

IR: That’s because he wronged Lawrence. In #LawrenceHive’s mind, he’s the enemy. Issa cheated. But also, we haven’t really gotten a chance to be in Daniel’s world, and I think that’s what this season is doing. It’s painting Daniel as a whole, three-dimensional character. We’ve only seen him through the eyes of Issa and the investigative eyes of Lawrence. We don’t really know who Daniel is. Hopefully, men will feel torn in identifying with Daniel’s character.

Daniel (Y'lan Noel). (Merie W. Wallace)
Daniel (Y'lan Noel). (Merie W. Wallace)

TL: In the first episode of Season 3, we find out Issa’s a Lyft driver, and she welcomes passengers to the “party Lyft.” She’s got snacks in there — even Capri Sun. Do you still take Lyfts? What’s your ideal party Lyft?

IR: I was just in Atlanta for two months, and Lyft was how I got everywhere. I don’t know if I can handle a party Lyft. I would have to be with friends for sure. I can’t be in nobody’s party Lyft by myself. I would have to experience that with close friends. My party Lyft would have to have some drinks. I know that’s not legal, but my driver would get a huge tip — as long as he or she were not drinking. I like champagne, prosecco or bourbon, anything dark. What kind of snacks? I guess popcorn, chocolate. I’m a chocolate person. That would be ideal, but then I would never want to get out of the car. Sometimes the car ride up to the event is so much more fun than the actual destination.

TL: Can you talk about the dynamic in the writers’ room and what perspectives you enjoy?

IR: I love varying perspectives. A lot of us are black women, and we agree on some things, but none of us are the same. I love when we disagree. We’re all different ages and sexualities. You get very varied perspectives, and you try to include them to make our audience think and discuss. Our male to female ratio is also interesting.

And those also often make it into the show.

Issa Rae. (Taylor Jewell/Invision/AP)
Issa Rae. (Taylor Jewell/Invision/AP)

TL: With Color Creative and Issa Rae Productions, you’ve been really entrepreneurial in your career. A lot of women are starting production companies or already have one, like Mindy Kaling, Reese Witherspoon and Lena Waithe. Why do you think women are creating their own companies to uplift their content?

IR: Because we realize that if we don’t open the door for others, this moment will pass. The difference between now and the ’90s, when there was a huge boom, is that networks made you feel like you had one shot. We got one slot. So you were kind of combative in making sure you could secure your spot. You were led to believe that there weren’t going to be other opportunities, so as opposed to helping people up the ladder, you were sometimes kicking it down.

To give people the experience to actually be in positions of power down the line so they can open the doors for other storytellers. You know, that’s what’s so powerful about this moment. We’re not being competitive, we’re just like: “You got a show? Great. Who’s working on your show that I can bring on mine? Who do you know?” It’s so great. It’s so fun to be able to support the shows of my friends and to see that they’re in it and looking fly and beautiful.

TL: I’ve seen on social media that you’re friendly with Tiffany Haddish, and when you were interviewing her for “A Sip,” you said you tried her food. What’s the best meal that she’s cooked for you, and how did you become friends?

IR: She has her staples. I’ve had her fried chicken, collard greens and kale. It was delicious. She seasoned the hell out of that chicken. She’s a great hostess.

We met each other for the first time on the Jay-Z [“Moonlight"] video that we got to do, and I’d heard her name multiple times. But I just had never met her or crossed paths with her. We got to really kick it in New Orleans right after “Girls Trip” premiered. I went to their little private screening, and she immediately called me afterward and was like, “So where’s the party at?” It was like, party friends forever.

TL: What was better: Hugging Beyoncé and hearing her say you were beautiful or talking about “Insecure” with President Obama? And has anything in 2018 topped either of those moments?

IR: President Obama and Michelle Obama are tied.

Need help digesting each episode of “Insecure”? Crissle West and Francheska Medina host the podcast “InsecuriTea," an aftershow of sorts. (Fun fact: West also hosts “The Read” with Kid Fury. A sticker for the podcast, along with one for “Another Round,” is featured in Issa’s cubicle on “Insecure” this season.)

This “Insecure HBO” playlist on Spotify and Tidal updates every week with music featured in each episode.

Kelli (Natasha Rothwell). (Justina Mintz/HBO)
Kelli (Natasha Rothwell). (Justina Mintz/HBO)

Jezebel culture editor Clover Hope — the same woman who Beyoncé spoke to for Vogue’s September issue — interviewed “Insecure” writer and star Natasha Rothwell, who plays Kelli on the show.

If you enjoyed “Due North,” the parody series within a series, last season, keep your eyes peeled for “Kev’yn" this year. It’s a ’90s-era reboot, reminiscent of “Martin” and “Living Single.”

Editor’s Note: This article originally misstated that Jay Ellis would not return as Lawrence in Season 3. It has been updated to reflect the possibility of his return.

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