Choices, Okay?! – Insecure Season 5, Episode 8 Recap

Photo Credit: Merie Wallace

This post is in partnership with HBO. As always, thoughts and opinions are my own.

Sharing – Issa and Nathan are laying in bed at her place and she’s thinking about how Tiffany is going to be moving away soon. He says they’ll have someone to go see, as he puts on his boxer brief. They have an ease to their exchange that feels so intimate. In the bathroom, he takes some medication, and she shows up wearing one of his shirts, which he left over there. He mentions how he’s been leaving a lot of stuff over at her place and she says, “Looks like mi casa is starting to look like WE casa.” Nathan says he likes waking up next to her and poses the question of whether they should move in together. She asks if they’re ready for it, and they agree to give it more thought. WOWWW huge step! As she’s brushing her teeth, he tells her that’s his toothbrush. GAGGGG. 

The BLOCC’s latest event is off to a great start, with art, food, and vendors. Seth is walking it with Issa, and he’s pleased. The Anthology Collective even agreed to be vendors, even though they were Team Crenshawn before. Seth says he’s gonna send her an offer soon. WIN.

Nathan and his cousin show up to support and they love the event. Issa’s dropping “my man” left and right and, it’s really cute. She even calls her and him a power couple. Sis is smitten (or laying it on thick for some reason). They leave by exchanging “I love yous,” which Kelli and Molly show up in time to tease her for. 

Photo Credit: Merie Wallace

Molly’s smiling too, and it’s cuz she’s texting Taurean. Date number one went well, date two is the next day, and it might be when she lets him get some! It’s a welcomed distraction from estate planning stuff with the Carters. 

Offers – Issa and Quoia take stuff to the car after the event and up walks Crenshawn. WHAT NOW?!? He is there to give Issa her props and make peace, admitting that event planning ain’t easy at all. He tried to throw a wearable art gala but didn’t know all the legalities of it, so that didn’t go well. He does a “lowkey” apology and proposes that they team up again. UMMMMM… after ALL THAT SMOKE you been giving her? Now you wanna work with her? Sir… TF?!? He tells her to give it thought.

Photo Credit: Merie Wallace

Issa’s at home when an email comes through from NBW with the offer to officially partner with The BLOCC. The offer is RIGHTTTT and the money is RIGHTTT and Mirror Issa is even more GEEKED than real Issa. Things are really looking up for my girl!

Glow Up – Issa meets up with Team NBW and Quoia to show them a theater she wants to use for a concert for the Anthology Collective. It can fit four hundred. Cut to, she’s showing them a venue that can fit six thousand and three hundred. Then, she’s doing an interview with Elaine Welteroth (hey boo!) in front of a huge crowd about how much The BLOCC has grown in the last two years. Shoot… she’s fancy AF in first class where her neighbor is Ty Dolla Sign. Ty’s headed back to LA to work with Crenshawn, who is now a hood hero. 

At her beautiful home, Nathan greets her and grabs her bag. He has a new shop, and this house is where they moved to a year before, to be closer to NBW offices. They’re in West Hollywood now. She seems to be out of touch with what’s happening in LA, like who’s creating buzz and even where to hang out. Her hair is bone straight too.

But really, none of that has happened yet. It’s just her, in front of the mirror, holding this NBW offer, daydreaming about where it could take her. Right then, she gets a text from Crenshawn, asking her to meet up with him.

Planning – Molly is walking her parents through estate planning and Kelli is there to help. The Carters say the three kids should just split whatever they leave behind, but it’s not that simple. How much do they actually have? What’s in their 401K? Well, not much, because Mr. Carter borrowed from it to pay Mrs. Carter’s medical bills. There is a lot of unspoken shame there.

Issa meets up with Crenshawn and tells him she doesn’t think they should team up. He states his case and says he wants to show her he’s serious. She agrees to give it some thought and let him show her the space he wants to develop. Her and Quoia meet up with him, and the space is dope. Which leads to them creating a flagship store that is so successful, they open another a year later. That one is also dope. She’s a known entity in the community. A bus drives by and she sees a bus draped with an ad of a Ty Dolla Sign holding NBW-branded water. Issa gets awarded the key to the city from the Mayor of Inglewood (hey Tyra Banks!) for her work uplifting local Black businesses. She even has her a commemorative day in her honor! 

She comes home to Nathan, who’s made her some drinks. Their apartment is the same. In fact, she’s still having to deal with neighbor Trina’s complaints, as building manager. Being an entrepreneur is some real work with real sacrifices. Nathan says he’s proud of her, as she walks into another room.

When she walks out, it’s no longer Nathan who is proud, but Lawrence. Telling her he’s proud. He leans in to kiss her and she snaps out of this massive daydream. She’s freaked out!

Old Habits – It’s late when Kelli leaves the Carters’. She had a ball and bonded with Molly’s mama! She even enjoyed the estate planning part and feels like she wants to do more of it. When she leaves, Molly tells her dad she’s proud of him for pushing through the tough parts of that. She leaves to head home and is exhausted. She starts to cry over her steering wheel when her phone rings. It’s Taurean, who says he’s about to come get her. She says she had a tough day, and that she doesn’t think she’ll be good company. He tells her it’s fine. 

Photo Credit: Merie Wallace

Issa’s at home pacing and Mirror Issa is wondering why she’s so stressed. Issa’s wondering why Lawrence popped up at all and Mirror Issa asks whether it’s because they still got unfinished business. 

She calls Molly to talk about this tough decision she needs to make. Molly tells her that there is no wrong answer here, and that she needs to follow her gut. Issa hears her, and Molly hears a knock at her door. When they hang up, Molly opens the door and there’s a drink delivery for her and some food. They’re from Taurean. AAWWWW. 

Nathan brings food over to Issa’s and goes to wash his hands. When he does, she hears Lawrence’s voice tell her he wants her to be happy. She is spooked!

Issa’s at a crossroads professionally and personally, and I believe that her decisions should actually be easier than she’s making it. She’s wrestling with ghosts instead of what is actually tangibly in front of her. 

Professionally, she’s struggling with whether to go with the NBW offer, which would put her under the umbrella of their company. Or should she take a risk with partnering with Crenshawn? I’m not sure why Issa thinks she has to do either/or. I think there’s room to do both. She can take NBW’s money and structure, while using her access on the inside to continue to do the work with artists like Crenshawn, providing resources for the vision. She’s gotten enough trust with NBW where she can push back on notes that may alter the artist’s vision. She can use the leverage of past events to stand strong and insist on backing those she brings in. PLUS, NBW LOVED Crenshawn. YOU AIN’T GOTTA CHOOSE. Do both!

Issa’s so used to the struggle, that in a moment when she can have EXACTLY what she wants, she’s forcing herself into making choices she doesn’t even have to. You actually don’t have to lose sight of where you came from when you become successful. You don’t have to lose your grounding or base just because you’re making more money. The Issa daydream where she’s highly successful and her hair is straight, is anxiety and fear. “What profits a man who gains the world and loses his soul” in daydream form. 

Her personal dilemma is also one she doesn’t really need to have. She’s responding to the ghost of Lawrence, who ain’t there. When right in front of her are all the makings of a relationship that could be strong and lasting, which is something she’s wanted. Nathan has even presented the option of them moving in. She has what she wants, but the Anxious Mind tells her that maybe this isn’t it. So she is going back to her old pattern of self-sabotage, which I hope she doesn’t lean into. She keeps looking backwards and I’m not sure how she’s supposed to move forward like that. 

Shoutout to Molly for doing the important work of making sure her parents have done their estate plan. Sis was tired, but I hope she’s really taking stock of Taurean’s actions. He’s feeling her, and I hope she doesn’t do some foola** thing to mess this up. 

Two more episodes of Insecure, and we say goodbye. I’m excite-scared.