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Home - TV Shows - Insecure: Season 5/ Episode 8 “Choices, Okay?!” – Recap/ Review (with Spoilers)

Insecure: Season 5/ Episode 8 “Choices, Okay?!” – Recap/ Review (with Spoilers)

As a HUGE opportunity comes Issa’s way, so comes the question of what life will be like whether she does or not?

ByAmari Allah Hours Posted onDecember 12, 2021 11:48 PMJune 9, 2023 9:21 AM Hours Updated onJune 9, 2023 9:21 AM
Crenshaw, Issa and Quoia looking at the place where "We Got Y'all" used to be

Spoiler Alert: This summary and review contains spoilers.


Additionally, some images and text may include affiliate links, meaning we may earn a commission or receive products if you make a purchase.


  • Recap
    • So This Is What Being Loved Right Is Like? – Nathan, Issa, Molly, David, Olivia, Kelli, Taurean
    • The Corporate Route – Issa, Nathan
    • The Down With The Homies Route – Issa, Crenshaw, Lawrence, Nathan
    • Things To Note | Question(s) Left Unanswered
      • Question(s) Left Unanswered
      • What Could Happen Next
  • Review
    • Highlights
      • The What Ifs
      • Kelli Putting Molly's Parents At Ease When Estate Planning
      • Molly Got A Good Man!

Issa has come to a point in her life when she is not choosing between struggles but favorable options. As this happens, Kelli reminds us she is far more than comic relief.


Aired 12/12/2021
Network HBO
Directed By Kevin Bray
Written By Eli Wilson Pelton

Recap

So This Is What Being Loved Right Is Like? – Nathan, Issa, Molly, David, Olivia, Kelli, Taurean

Issa and Molly are so good and so in love. Well, Issa is in love. I’m talking about thinking about having Nathan move into her home kind of love. As for Milly? Taurean is just showing himself to be that dude. Prime example, when Molly is just not into or has the energy to meet up, rather than pitch a fit, make critiques, do the most, he sends some wings and wine to her doorstep.

But, Kelli really shows what it means to be there for your people when it comes to love. As we’ve seen, David and Olivia, Molly’s parents, don’t like talking about money and when it comes to making a will and estate planning? They’d rather keep it simple, not get into any specifics, and pretty much leave it to their kids to figure out.

Olivia and David getting frustrated talking about money

Kelli, using humor to defuse the intense feelings which come from the situation, is able to help everyone navigate through many a tough conversation. This does take a good part of the day, but  Kelli gets it done. In fact, she enjoyed the process so much it seems she may try to help Black folk plan things out like this on a regular basis.

The Corporate Route – Issa, Nathan

So, Issa gets an offer from NBW, and so now she has to decide if she wants to go corporate or not. On the one hand, making nice money means a whole new lifestyle for her. With Nathan included, she can get a new place, travel, and really live the dream.

However, she’ll have to give up working for and with the community as she has done in the process and be willing to become a stranger.

The Down With The Homies Route – Issa, Crenshaw, Lawrence, Nathan

The alternate to this is that she can link up with Crenshaw, who is starting to act right since he realized permits, and all that Issa does for events isn’t easy to pick up. Now, this method does have some risk, but the reward is Issa staying in Inglewood, doing the work, providing opportunities, but then comes the issue of her still living in the same apartment. Also, Nathan seems to exit this dream, and Lawrence enters so, Issa is at a bit of a crossroad and unsure which dream she wants, why, and if either will make her happy?

Things To Note | Question(s) Left Unanswered

Question(s) Left Unanswered

  1. So how much were they offering Issa?
  2. Did Crenshaw ever do a public apology like he publicly disparaged Issa? I feel like him coming to Issa, tail between his legs, shouldn’t have been enough for them to talk business.

What Could Happen Next

  1. I think Issa getting with Crenshaw might be the move with two episodes left. Especially since her getting to purchase the building “We Got Y’all” had would be the move. For as much as Issa may want big money, I think what she mainly wants is a purpose, and working for her community is more in line with that than working to keep a nice house and to use frequent flier miles.

Review

Highlights

The What Ifs

It isn’t known whether Insecure will end on a cliffhanger, give us an epilogue, or what. So this what if? It allows viewers to see different paths Issa can take and, as the show has done since the beginning, debate what would be best for Issa. And while the show will likely settle on something, I think enough is presented to keep that conversation going to the point that, weeks and months down the line, someone will keep a social media thread going about how Issa should have done this. Just as much as people still think Daniel was the one and needs to make an appearance.

Kelli Putting Molly’s Parents At Ease When Estate Planning

While we seemingly won’t get a Kelli episode, we are getting a notable amount of Kelli screentime to placate us, and I’m not mad at it. Especially since this episode allowed Kelli to both be funny and helpful. She walked Olivia and David through a confusing and painful process. One that, as David says, forces you to realize that, while you did okay, you didn’t necessarily build generational wealth. You just made enough to pay bills and raise your family. Which there is nothing wrong with, but it can be humbling looking back and seeing what you have to leave for those with a long future.

But, what we perhaps appreciate the most out of all of this is that we were reminded that, alongside Kelli’s intelligence regarding accounting, she has emotional intelligence. Yes, a lot of the time, Kelli has been a hot ass mess, but every now and then, you realize, be it her drinking, smoking, or just trying to have fun, Kelli is multi-layered and can’t fully be judged by her most extroverted moments. You just have to pay attention to see how she contributes to the friend group in ways most don’t give her credit for.

Molly Got A Good Man!

Molly exasperated after a long day

You know, communication is nice and all, but sometimes you just want to find someone who gets it. That person you don’t have to explain yourself to. Someone who doesn’t get in their feelings, accepts what you feel on face value, and knows how to still show they care, even when disappointed. It sort of gives you hope after the show made dating seem like a trash move for so long.

[ninja_tables id=”46733″]

Crenshaw, Issa and Quoia looking at the place where "We Got Y'all" used to be
Insecure: Season 5/ Episode 8 “Choices, Okay?!” – Recap/ Review (with Spoilers)
Trajectory: Climbing
We've been in the struggle with Issa for four seasons and nearly ¾ of this one, but things are looking up. She got a good man but may want that old thing, has an offer of a lifetime, but could also stay independent and do well. This is aspirational. For what really says life is good beyond you having multiple options, with few, if not none, leaving you exhausted – in a bad way.
Highlights
Molly Got A Good Man!
Kelli Putting Molly's Parents At Ease When Estate Planning
The What Ifs
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Related Tags: Eli Wilson Pelton, HBO, Insecure, Insecure: Season 5, Kevin Bray

Amari Allah

Amari is the founder and head writer of Wherever-I-Look.com and has been writing reviews since 2010, with a focus on dramas and comedies.

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