Insecure Recap: The Road Less Traveled


Choices, Okay?!
Season 5 Episode 8
Editor’s Rating 5 stars


Choices, Okay?!
Season 5 Episode 8
Editor’s Rating 5 stars
Photo: Merie Weismiller Wallace/HBO

In last week’s episode, the women looked at their lives and tried to determine how they’d want their futures to look. This week, we hone in on Issa’s vision for her future, her dreams for The Blocc, and the truth of where her heart lies.

It opens on Issa and Nathan in bed, contemplating Tiffany’s imminent departure. Later, Issa points out that he’s been leaving a lot of clothes at her place (she’s claimed his T-shirt), and Nathan takes it as an opening to suggest that they move in together. Issa is surprised at the suggestion but agrees to think about it.

At The Blocc’s L.A. Art Walk, Issa chats with Seth, the rep from NBW who has been sponsoring her work, and he tells her that she’s been doing great work and to expect a formal offer from the company soon. Later, she runs into Nathan and his cousin Thomas shopping. When the men head off, Molly and Kelli rib her about their Black Love™. Molly gives updates on her dates with Taurean and her parents’ estate planning. Getting them to take their mortality seriously has been difficult. Thankfully, Kelli steps forward and offers to sit down with them.

After the art walk is over, Issa and Quoia run into none other than Crenshawn, who’s been waiting to catch up with them. He apologizes for how things ended between them and admits that he hasn’t had much success holding events independently. Instead, he has a proposal — they should team up and keep working together in the community. More than anything, Issa seems impressed by Crenshawn’s audacity, but … she doesn’t say no. Later, while fixing her hair in the bathroom, Issa finally gets the formal offer from NBW, and it’s lucrative.

In what seems like a time jump, Iss and Quoia meet up with the NBW exec to go over the details for an event venue that holds about 400 for The Blocc. Cut to: A leveled-up Issa walks NBW through a new venue, this time big enough for 6,300 people. She details their brand penetration in the Black community and is flanked by Quoia and two new assistants. The Blocc is leveling up too. We then see Issa onstage in Detroit chatting with none other than Elaine Welteroth about The Blocc and its longtime partnership with NBW. When Elaine asks if she’d like to plug anything from L.A., Issa admits she hasn’t had much time to do anything in the city for quite a while.

Issa boards the first-class cabin of her flight back to Los Angeles with a glamorous blowout. Her hair has been getting straighter and straighter as the scenes progress and she rises in status and wealth. She glances across the aisle and spots Ty Dolla Sign, who’s on his way to collaborate with, you guessed it, Crenshawn. It seems that in the time since she’s been away, Crenshawn has managed to fashion himself into a local hero. The city loves him. At this news, Issa looks uncomfortable. She passed on the opportunity to work with him when she had the chance. It’s the first time we see her seem to question her choices.

When she gets back to L.A., Nathan greets her in their palatial new home. They’re doing well, living together and in love. As they make out on the couch, Issa pauses to ask when they moved. Nathan tells her it was last year. They’re now in West Hollywood to be closer to the NBW offices. Then … we’re back at the mirror where we began. It was all an elaborate fantasy — a “what if?” scenario of accepting NBW’s offer. So far, Issa seems into it. Just then, Crenshawn texts her with a pin at the location of the new store he’d like to open.

Back with Molly, she, her brothers, and Kelli walk Molly’s parents through their estate issues. The children all have questions about their parents’ wishes, but Carol and David are uncomfortable getting into the nitty-gritty of the details. Kelli smoothly steps in to reassure them that estate planning doesn’t have to be scary or upsetting. David laments that he’s worked all his life and feels like he has little to show for it — a theme that feels sadly familiar for Black families. But Kelli tells them that for now, all they need is an accurate financial picture of their lives to start building on.

Later, Issa and Crenshawn meet up for coffee, and she tells him that she doesn’t think working together is the right choice for them. But Crenshawn presses, touting the new retail-and-event space he’s found. It’s perfect for continuing the work that The Blocc is geared toward. He tells her that he’s serious about teaming up and has even sent over an official proposal. He wants this, so Issa takes him seriously.

Issa and Quoia meet up with Crenshawn at his studio for a walk-through like he requested. Cut to: Issa, dressed in one of his designs, is introduced to Crenshawn’s team during what looks like a fashion installation. Next, Issa takes Crenshawn to an empty storefront she wants to use as their second location. They’re also getting press in the Los Angeles Times. She assures him that after running the numbers, she’s confident they’re ready to expand.

There’s a line around the block on the second location’s opening day. Issa is such a staple in the community that the ice cream man knows her favorite and gives her a scoop for free. As she enjoys her treat, a city bus rolls by plastered with a massive ad. Ty Dolla Sign is the new spokesperson for NBW.

Later, Issa — massive curly Afro in tow — accepts the key to the City of Inglewood from Tyra Banks (lol, sure) for all of her work in the community. The day is officially declared Issawood Day. Back at home with Nathan, she asks why they never moved into a bigger place. He tells her it’s because she made sacrifices to be an entrepreneur — oh, and by the way, one of the tenants is still dealing with a plumbing problem. Dressed to the nines, Issa heads for the plunger in the bathroom, but when she gets back to the living room, it’s not Nathan waiting for her; it’s Lawrence. And he’s telling her how proud he is of all the hard work she’s done. When he moves to kiss her, she screams. And we end up right back after that coffee meeting with Crenshawn.

Back with Molly, Kelli says good night after a long day of working through David and Carol’s finances. When she’s gone, they thank Molly for pushing them to get it done. She tells them she’s happy to have done it and that she loves them, but when she gets to her car to leave, she breaks down. Planning for the eventuality of her parents’ death has been hard for her too. She’s still teary-eyed when Taurean calls about their date. She admits that she’s unlikely to be much fun after the rough day with her parents. Taurean takes it in stride and tells her he’s available if she wants to talk.

At her apartment, Issa mulls over the two paths available to her with Mirror Issa. She’s perturbed that Lawrence showed up in her fantasy and thinks it means she shouldn’t work with Crenshawn. But Mirror Issa says that she called Lawrence just a few weeks ago (in the last episode), and his appearance in her vision for the future must mean things aren’t done between them.

Issa calls Molly to mull it over some more and tells her that she’s worried that working with NBW would make her a sellout but that betting on Crenshawn would be too big of a risk. Molly sagely tells her that there’s no wrong answer. Either option would serve her well. She just has to trust her gut. They hang up with quick “I love you”s, and Molly gets a knock on the door. It’s a delivery of wings and wine that Taurean has sent over to lighten her mood. He might be a keeper!

At home, Nathan and Issa are getting ready for dinner when it happens again. Nathan calls to her from another room, but she hears Lawrence’s voice. She waits expectantly but is visibly deflated when it’s just Nathan who walks back through the door. With two episodes left in the season, it seems inevitable that the season is heading straight back to Lawrence after all.

Week’s Best Woot Woots

• “I guess I do be leaving a bunch of shit here. My drawers, my shirt. Pants, shoes. I guess I could have just said ‘clothes.’” — Nathan

• “Love blackly. Walk safely.” — Quoia

• “I’m just gonna say what everybody’s thinking. We a power couple!” — Issa

• “My great-aunt used to always say her will is with God. It wasn’t. It was with the county. They got her house now.” — Issa

• “Can’t believe him! With that sexy-ass apology.” — Quoia

• “Bars weak, but the bank account bussin’!” — Mirror Issa

• “Look, I wasn’t onboard before, but now I see you was the one playing chess. Moving bishops and shit.” — Quoia

Insecure Recap: The Road Less Traveled