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“Insecure” Recap: Season 5, Episode #8: ‘Choices, Okay?’

In the episode before the penultimate episode of “Insecure,” we can really see them beginning to set up the finale of the series. From estate planning and wills to dreams deferred, the characters are thinking through some really big decisions that will really change the course of their lives–or at least the people around them. 

To start the episode off, the writers try to establish that Issa and Nathan are doing really well. They’re sleeping together. Issa is telling Nathan the type of things she only talks about with Molly or in the mirror with herself. Nathan is taking his medicine, and he even proposes moving in with Issa. Things appear to be good with the Issa-Nathan dynamic now. 

As for Molly, she’s really being driven crazy by her parents, who after her mom’s scare, still aren’t moving quickly enough on getting their estate in order. Kelli decides to offer her services, and together with Molly, they have to pull teeth in order to get Molly’s dad to open up about his finances. He does pose the greatest question ever, why don’t they just take what he has when dies and split it up? But then what would we need accountants like Kelli and lawyers like his daughter for? 

As for Issa, with her love life seemingly in the right place, the only “insecure” thing to examine about her is her professional life. Oddly enough though, things are going amazing there. The community is recognizing her, MBW loves her work, and she’s getting opportunities from creators, artists and brands on a somewhat regular basis. Because of this success, Crenshawn rears his mean head again. Now he wants to partner with Issa and see if they can work together on some of the ideas he has for a multi-purpose space where they could sell and showcase his fashion. 

Issa is hesitant to take him up on the offer. Plus, MBW has now made her a “rich bitch” offer to, we presume, work with them exclusively in reaching black audiences. Issa is super excited about finally getting this bag, and suddenly, we enter a dream sequence where she is in a major auditorium working with big time executives at MBW, she’s got a really big team, she’s being interviewed by Elaine Welteroth, is talking to Ty Dolla $ign (who says he’s working with Crenshawn) in first class, and lives in a luxurious home with Nathan. However, the dream takes a slightly bad turn when she realizes she’s kind of left the community of Inglewood behind. 

In her second dream, Issa imagines if she took another path and partnered with Crenshawn. In this sequence, we see her being welcomed by Crenshawn and his people, working with up and coming artists, opening a new star, being a fixture in the community, receiving a key to the city from Tyra Banks, and celebrated by her local media. However, instead of working with Crenshawn, it’s Ty Dolla $ign that’s now working with MBW. When Issa gets home, she still lives in her old apartment and is still the live-in super for the apartment complex. And when Nathan leaves the room (in this dream sequence), Lawrence pops up and says that he’s proud of her and goes in for a kiss. Issa screams, and yet, later in the dream, Lawrence’s voice pops up again. 

This clearly shows that Lawrence is on her mind, and so at the same time she’s at this fork in her career, she seems to be considering taking a different path in love from the one she’s on with Nathan. Issa Rae, in the Wine Down after show, hinted at the fact that she feels that people often consider all of the “what ifs” when trying to work through an important decision. So she kind of said this is just a thought process–not necessarily a sign that she wants Lawrence back in her life over Nathan. 

As a result, I’m at a loss. I don’t know if she’ll end up with Nathan or Lawrence. My most prominent thought is that the writers of the show wouldn’t dare end on a fairy tale like ending, as they probably don’t want to insinuate that such an ending is realistic. Still, at this point, it would take quite some hoop-jumping for Issa to end up with Lawrence given her current predicament, which would make for some much needed drama in the final 2 episodes. If nothing else, we know that she’s going to be forced to make a decision, right? She’s not just going to not see Lawrence at all in these final 2 episodes. Actually, I’m not sure the two have had any kind of closure on their relationship since the breakup, so the show is going to give us that, right? 

Right? 

Maybe? 


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