*Warning: Spoilers ahead*
- Issa moves into her new digs and attempts to get rid of old baggage.
- Molly struggles to find her place at her new firm and decides to cross some of her co-workers to get ahead.
- Issa reconnects with Nathan (yep, the Lyft rider) and they share a day of fun.
- Issa gets the courage to make a move and finally says buh-bye to We Got Y’all.
Dive into Insecure episode four, the water’s fine.
Season three, episode four of Insecure, titled “Fresh-like” opens on Issa (Issa Rae) getting back to her signature mirror rapping in the bathroom of her new crib. Daniel (Y’lan Noel) knocks on the door and drops off the last of her things. She tells him she appreciates him, and he cuts her off and says “You don’t have to do all that,” before things get too sentimental. They hug and say goodbye but he’s clearly salty.
As Daniel leaves, Molly (Yvonne Orji) arrives with some boxes Issa stored at her place and brings a couple of housewarming gifts: a foam mattress, a plant even Issa can’t kill and some “next level” Hennessy because Issa is a “next level” kind of girl. Molly launches into a pep talk about new beginnings, but Issa cuts her off and says any time she tries to make big changes she falls back on old habits. So, they get to unpacking and Molly tries to convince Issa she has no use for the CDs Lawrence made her after their first date or Forever 21 earrings (“They last forever”). They’re interrupted, however, when a tenant knocks on the door convinced there are squirrels living in the walls and says Issa needs to fix it ASAP.
Later that night, Issa continues unpacking, and just when it seems she’s on a roll getting rid of unnecessary things, she decides to keep some of it. Those old Lawrence mix CDs of Adele? They’re “rolling in the keep.” She also stumbles on her high school rap journal and reflects on how simple life was back then.
The next day, Frieda (Lisa Joyce) approaches Issa at her desk and gives her some good news: Joanne (Catherine Curtin) has finally agreed to let her return to the field and We Got Y’all is changing their tone-deaf logo.
Meanwhile, Molly complains to her therapist that she’s not quite sure where she fits in at her new company. She made a move so she could be the star of her law firm, but things aren’t panning out the way she had hoped. Her therapist suggests she focus on how she can be helpful to the firm, but Molly instead launches into a diatribe, “I just don’t want to allow myself to keep getting comfortable in a bad situation. I don’t have time for that. After Dro, I’m only interested in making moves that take me where I want to go.” Her therapist rightly asks who Dro is and Molly glances around awkwardly. Looks like someone hasn’t been forthcoming.
Back in the office, Molly decides to take her therapist’s words into account. She approaches the other women at the firm and asks how she can help. It’s against her nature, but she wants to make this work. Then again, she can’t shake the feeling that she might be able to make more of a splash if she hitches her wagon to one of the cockier guys in the office. Later, when the ladies ask if she wants to go over the case that evening, she fumbles for an excuse until a male co-worker interjects asking if she’s ready to go over another case. They realize that Molly is only interested in getting ahead, not being helpful.
Issa celebrates her work victory with a salmon taco from Worldwide Tacos, but before she can dive in, Nathan (Kendrick Sampson), the handsome Lyft rider who tipped her $50 (and got in a fistfight in her car) approaches her to say hi. She drops her taco and can’t remember his name, but they catch up and he treats her to a new taco. They order, but the wait for their food is going to be an hour, so, while Nathan (new nickname: Nanceford) continues to talk trash about L.A., they walk around the neighborhood. He’s flirting with her, but she’s playing it cool. Then, before they can get those tacos, Frieda texts her and asks if they can meet to go over her new school assignment.
So, Issa and Nathan start to head back to her office and he proposes they play truth or dare. When Issa says truth, he asks when her last relationship was. She answers that it lasted five years (we miss you, Lawrence) and ended because she cheated. He appreciates her honesty and as they continue to talk he asks if he can see where she grew up. On a whim, she calls Frieda and tells her she’s “feeling sick.”
They pull up to the neighborhood where Issa grew up, and she shows him the literal mansion she used to live in. He calls her bougie and she laughs, saying that her parents scraped together everything they had to afford the place. Alas, they got divorced after installing a pool and Issa and her brother never got to enjoy it. She remembers thinking, “Can’t y’all stay together for the kids…to swim?”
He dares her to break in, so she lets them into the backyard and dares him to jump in the pool naked. He’s not down, but she says, “You got me out here being all felonious and you can’t jump in the pool? You scared?” Not one to be labeled a chicken, he starts to strip while Issa watches. He dares her to jump in too, so she takes off her clothes and hops in.
As they swim about, she shows him the rock she used to hold her family talent shows on and opens up to him about her rap journal. He asks if she’s going to write a rap about him and she says she doesn’t know him like that but insinuates she might like to. When she asks about his last relationship he says he hasn’t really had one and that he always wanted to move to L.A. (even though he talks poorly about it on the reg). Turns out, his apartment in Dallas flooded during the hurricane and he decided to just leave and start fresh. “Sometimes you just gotta go for it even when it don’t make sense to everyone else,” he says. That’s just what she needs to hear.
Just then, the owner of the house calls out and they make a break for it. They return to the taco stand to collect their bounty, then Issa suggests they go back to her place to eat them. She’s been talking a big game about how good these tacos are, so he digs in and jokes that they’re just “all right.” Soon, they start kissing and it’s romantic…until one of the tenants, a little boy, knocks on the door and says he and his mom are locked out. Noticing there’s a dude in the apartment with Issa, the little guy inquires, “What y’all doing? Eating tacos and kissing on the mouth?” So, Issa and Nathan say goodbye and he says they should do this again.
The next day, Issa decides to finally throw out the box of random stuff she’s been hanging on to. Still in a fresh beginnings mentality when she arrives at the office, Issa tells Frieda that she’s quitting because she needs “something new.” She walks out of the office and off to figure out what to do with the rest of her life.
Will Issa finally try her hand at rapping? Will she and Nathan become an item? And how is Molly going to deal with the fallout of being shady at the office? All those questions and more will (hopefully) be answered when Insecure season three, episode five debuts on HBO on Sunday, September 9 at 10:30 p.m.