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Issa Has 2 Jobs and Still Can’t Pay Rent in Insecure’s Season 3 Premiere

Like many millennials, Issa is struggling to make ends meet, sleeping on a friend’s couch and moonlighting for Lyft.

Insecure stars Issa Rae, Natasha Rothwell, and Yvonne Orji.
Issa Rae, Natasha Rothwell, and Yvonne Orji at Insecure Fest in Los Angeles.
Photo: FilmMagic for HBO

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The season three opener of Insecure has it all: steamy sex, relationship drama, workplace tensions, and a “party” Lyft. While romance and friendship have been hallmarks of the show from the outset, the third season, which debuted on HBO Sunday, already stands out from the rest because the heroine, Issa, desperately needs a financial boost.

She’s working two jobs without a place of her own and no foreseeable end to her cash flow problems. As affordable housing shrinks and wages remain stagnant in Los Angeles, where the show is set, Issa’s predicament is one many viewers will find relatable. Previous seasons of Insecure explored how rough the job market is and the impact of gentrification on communities of color. Given the fact that Issa is now the most economically vulnerable she’s ever been, Insecure’s third season promises to distinguish itself by giving fans the messy relationships they’ve come to expect along with a deeper look at Issa’s financial woes and what she can do to overcome them.

At the end of season two, rising rent at the Inglewood apartment complex Issa lived in for years signaled that gentrification had made its mark on the mostly black and Latinx city outside Los Angeles. At Insecure Fest, the LA block party where season three had its red-carpet premiere on July 21, star Issa Rae told Racked she thought gentrification was an important topic for the show to explore because Inglewood has changed rapidly since Insecure’s first season, which aired just two years ago.

“There’s so many places we shot that don’t exist anymore,” said Rae, who is also the show’s executive producer. “The show’s like a time capsule for Inglewood, for South LA.”

Insecure star Y’lan Noel.
Y’lan Noel (Daniel) at Insecure Fest in Los Angeles.
Photo: FilmMagic for HBO

On Insecure, gentrification has the same effect on Issa as it often does on economically distressed people in real life; it drives her out of her apartment. Without her now ex-boyfriend Lawrence to split the rent with, Issa moves out of the unit and ends up sleeping on her old flame Daniel’s couch. But Daniel, whom Issa jilted after cheating with him on Lawrence, has loud sex with other women in earshot of her. So why is Issa crashing at his place?

She can’t live with bestie Molly because the two have never come to a resolution about the time Issa stayed there years ago and supposedly broke a vase. Although Issa still denies any responsibility, Molly doesn’t believe her. But surely Molly isn’t the only support system in Issa’s life. Can’t she crash with literally anyone other than the resentful ex who flaunts all the hot sex he’s having in her face?

Rather than look for someplace else to stay, Issa weathers the discomfort of living with Daniel by driving Lyft at night. This is a new gig for Issa, who still has her demoralizing day job at an education nonprofit that’s just as crappy as its name, We Got Y’all. But if she makes so little money there that even moonlighting for Lyft she can’t afford to pay rent, why doesn’t Issa look for a new job?

It’s likely the show wants Issa’s predicament to reflect the struggles of real-life millennials stuck in dead-end positions they hate and can’t afford to leave, but it’s curious that Issa doesn’t even try to ditch her sucky job, complete with a manager who gives her a tongue lashing for trying to problem-solve. It doesn’t jibe that Issa, an intelligent and college-educated woman, has few to no career ambitions. What does she actually want to do with her life, beyond her romantic relationships?

Insecure hasn’t explored her life outside the men, and best friend, in it. Here’s hoping that the third season shines a light on its protagonist’s passions. What makes her tick? It’s certainly not her work at We Got Y’all or shifts driving for Lyft. Viewers know what the career goals of Molly, Daniel, and Lawrence are. Isn’t it time we learn about Issa’s too?

Insecure star Sarunas Jackson
Actor Sarunas Jackson at Insecure Fest in Los Angeles.
Photo: FilmMagic for HBO

While the fictional Issa may be broke, the real one is quite the opposite. We asked Rae and cast members Sarunas Jackson (Dro) and Natasha Rothwell (Kelli) at the premiere about their spending habits since they’ve been on Insecure. Last year, Racked also had the chance to catch up with Yvonne Orji (Molly), who told us that splurging isn’t really her thing. On the show, she plays a lawyer who wears everything from Stella McCartney to Cushnie et Ochs, but in real life, Orji is an H&M stan who loves a “really dope suit” and a bargain. In contrast, Rae is not afraid to indulge herself.

Issa Rae

Racked: Since starring on Insecure, what’s been your biggest spending splurge?

IR: A car. I got a Tesla in the first season. (Teslas can cost up to $80,000.) One of the writers was like, “You can’t buy a car.” But I needed one, so I bought it. [Later,] I got into an accident ... so Tesla sucks (laughter).

Racked: What’s the worst purchase you made or your biggest spending regret?

IR: I don’t have one. Probably going to a restaurant where the food wasn’t good.

Natasha Rothwell

Racked: Since you’ve been on the show, what’s been your biggest spending splurge?

NR: My dog. I got my dog.

Racked: What kind?

NR: He’s a goldendoodle, and his name is Lloyd Dobler. He’s named after [John Cusack’s character in] Say Anything, and dogs are very expensive. (Doodles cost anywhere from $500 to $3,000, not to mention the upkeep of owning one.) It’s like having a kid, but I’ve wanted one for so long. I’ve never had one before as an adult, so that would be the biggest thing.

Sarunas Jackson

Racked: Since you’ve been on the show, what’s been your biggest spending splurge?

SJ: I went to Topshop Topman one day, and I went in there with the intentions of getting a shirt, and I came out with three bags and spent $650. I didn’t want to do that; even though you’re blessed enough, it doesn’t mean you’re supposed to do that, and I felt bad, and I returned, like, half of it.

Racked: Oh, you did? Wow. So is that your biggest spending regret too, or do you have another one?

SJ: I spent money on a suit, and I regret not getting it tailored properly.