Wherever I Look
Recaps, Reviews, and So Much More
Home TV Series Insecure: Season 5/ Episode 7 “Chillin’ Okay?!” – Recap/ Review (with Spoilers)

Insecure: Season 5/ Episode 7 “Chillin’ Okay?!” – Recap/ Review (with Spoilers)

by Amari

A girl’s night in allows everyone’s favorite friend group to check-in, and over drinks, advice, and confessions are shared.


Aired12/5/2021
NetworkHBO
Directed ByAmy Aniobi
Written ByFran Richeter

Recap

Drinking, Smoking, Snacking, And Secret Tellin’ – Issa, Molly, Tiffany, Kelli

It has been three months since the group got back together, and Issa had planned out a spa day, followed by a nice restaurant, but plans changed with the spa having its pipe burst. Instead, the ladies decide to just stay in, drink a little, make some snacks, and do a college game involving a hat which pushes everyone to answer personal questions.

For the most part, these questions are harmless, though a bit nosy. We get the reveal Molly never saw Love Jones, that Kelli masturbates to thoughts of Derek, Tiffany’s husband, and most see Daniel as Issa’s finest ex.

Co-Parenting Is A Skill That Has To Be Built – Condola, Lawrence

Things are better than they were before between Condola and Lawrence. He is consistent, helpful, volunteers to help Condola with things that could stress her beyond Elijah, and things have become pleasant between Condola and Lawrence. In fact, they even bond in such a way that she feels comfortable talking about how she once contemplated an abortion.

This may lead you to think this vulnerability and time together have made them a couple again, but they seem to have just learned how to co-parent and maybe become friends again.

Adult Friendships & Relationships Require Effort – Issa, Molly, Tiffany, Kelli, Nathan, Lawrence, Taurean

As the night goes on for Issa and her friends, more notable reveals begin. For example, since the retreat, Molly reveals Taurean has been talking to her and checking in regularly, and she thinks something is there. Which everyone seems to encourage the exploration of. Then with Issa, after her friends confirm Nathan’s critique of her being inconsistent, she falls prey to her own issues and calls Lawrence, who doesn’t pick up but does hit her up later on.

However, the two big things are Nathan calling Issa and saying he loves her and Tiffany revealing she and Derek are moving to Denver due to a job offer. This is shocking for everyone, but especially Kelli. Once again, despite being the closest to Tiffany, she doesn’t learn about something beforehand but has to wait until the rest of the group is told.

But, rather than flip out, she reassures Tiffany, as do the rest of the ladies, and note that, while it will require more effort, they will all see each other again in this capacity.

Things To Note | Question(s) Left Unanswered

Question(s) Left Unanswered

  1. How long has Kelli been masturbating to the thought of Derek?

What Could Happen Next

  1. Can anyone else foresee a time jump during the finale?

Collected Quote(s) & .Gifs

Sometimes it’s not about making the smart choice.  It just has to make sense to you. And it doesn’t have to be the smart choice to be the right choice.
— Tiffany

You gotta be really intentional with the people you love.
— Molly

Review

Highlights

Co-Parenting – It Gets Better

As shown, a child is difficult to manage on its own, but alongside their existence comes the connecting of two people and their families. It creates almost an arranged relationship, which forces everyone to get along or at least attempt to, for the child’s sake. This, for many, is a challenge, especially if the parents fell out of love and have to both work on their friendship while raising a newborn.

Yet, as Condola and Lawrence showed, with effort, it can get better. Which, yes, may require one side to humble themselves, not just do things for the child’s benefit, but the other parent, but that bond is necessary. Otherwise, when things get difficult, which is guaranteed to happen, rather than be a united front, the single parent mindset will kick in, and, as we saw Condola do, decisions will be made with the thought of the non-custodial parent being secondary.

When Accessibility Wanes, Accountability Becomes Paramount

Friendships and relationships as an adult require intention. Once you are no longer in school and see that person because of sharing a class or being on the same campus, it means you have to put in the work convenience no longer provides you. For many, that means the end of their relationship.

This is why you have to appreciate all parties recognizing it won’t be easy, but they can make it work. When it comes to Issa’s friend group, it took 3 months, but they got back together, and while Tiffany moving to Denver will make things harder, the attitude thus far is that it means a vacation for those still in LA.

Then, when it comes to Nathan, his issue is going to be staying accountable for his part in the relationship with Issa. For while they do communicate, it is not at the level she needs to feel reassured about their future. More so, it is at the level he needs and often at his pace. Which, as shown, is much slower than Issa is comfortable with and a pace that drives her a bit mad.

Character Guide

Created

Collected Quotes

Not Created

Season Reviews

Season 2   |   Season 3

Episodes From This Series

Season 1   |    Season 2    |   Season 3   |  Season 4 |   

Affiliate Links
(If A Purchase Is Made, The Vendor Will Provide Us A Commission)

Amazon

Check Out The TV Series & Specials Page
TitleExcerpt
The Best of 2021 - Television & AnimeOriginally in order of season finales, but now in no particular order, here are many of the best shows whose season or series ended in 2021, or we only got a preview of.
Insecure: Season 5/ Episode 10 “Everything Gonna Be, Okay?!” – Recap/ Review (with Spoilers)Through a sometimes-dizzying number of time jumps, viewers get closure about where Issa and her friends end up in life, together, and in their relationships.
Insecure: Season 5/ Episode 9 “Out, Okay?!” – Recap/ Review (with Spoilers)What's supposed to be a going-away party for Tiffany and Derek gets interrupted by Molly and Issa's exes encountering who they are with now.
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?
Insecure: Season 5/ Episode 7 “Chillin' Okay?!” – Recap/ Review (with Spoilers)A girl's night in allows everyone's favorite friend group to check-in, and over drinks, advice, and confessions are shared.
Insecure: Season 5/ Episode 6 “Tired, Okay?!” – Recap/ Review (with Spoilers)With Issa's personal and professional life in turmoil, will this mean her taking a step back? Also, can Molly handle being away from her family, for work, during what can be her mother's final days?
Insecure: Season 5/ Episode 5 “Surviving, Okay?!” – Recap/ Review (with Spoilers)A health crisis tests not only Molly and Issa's relationship but Issa and Nathan's, which seems to be in a better than expected place.
Insecure: Season 5/ Episode 4 “Faulty, Okay?!” – Recap/ Review (with Spoilers)While not an entirely Nathan-focused episode, we are presented another opportunity to see how people live when not in Issa's presence.
Insecure: Season 5/ Episode 3 “Pressure, Okay?!” – Recap/ Review (with Spoilers)It's an episode solely focused on Lawrence and Condola during their son's first year and them working out how to co-parent.
Insecure: Season 5/ Episode 2 “Growth, Okay?!” – Recap/ Review (with Spoilers)We jump into a more stable future for both Molly and Issa, but what were the sacrifices made for what we see?
Insecure: Season 5/ Episode 1 “Reunited, Okay?!” [Season Premiere] – Recap/ Review (with Spoilers)It's the final season, and there isn't any fan service, but there is what long-term fans need.
Getting Ignorant With It: Episode 17 "Then God Snatched Their Hairline"Check out the latest episode of Getting Ignorant With It, "Then God Snatched Their Hairline."
Insecure: Season 4 Episode 10 "Lowkey Lost" (Season Finale) – Recap/ Review with SpoilersAs always, "Insecure" doesn't end its season on a whimper but instead leaves you in your feelings and ready to harass Issa Rae for another season.
Insecure: Season 4 Episode 9 "Lowkey Trying" – Recap/ Review with SpoilersAs Issa tries to find a way forward with Nathan and Lawrence, Molly is still trying to figure a way for others to admit guilt.
Insecure: Season 4 Episode 8 "Lowkey Happy" – Recap/ Review with SpoilersLawrence and Issa check-in and continue to have the type of conversations some wish they could have with an ex – if they believe in closure.
Insecure: Season 4 Episode 7 "Lowkey Trippin'" – Recap/ Review with SpoilersIn a Molly and Andrew focused episode, she meets Andrew's family, and a confrontation with them leads to some reflection.
Insecure: Season 4 Episode 6 “Lowkey Done” – Recap/ Review with SpoilersWith Issa trying to elongate her high from the block party, she seeks ways to keep that feeling going – which bite her in the ass.
Insecure: Season 4 Episode 5 “Lowkey Movin’ On” – Recap/ Review with SpoilersTo really show how bad things have gotten between Issa and Molly, what once was unthinkable happens at Issa’s block party.
Insecure: Season 4 Episode 4 “Lowkey Losin’ It” – Recap/ Review with SpoilersWe may have come to the point that led to Issa not messing with Molly no more – can you guess the reason?
Insecure: Season 4 Episode 3 “Lowkey Thankful” – Recap/ Review with SpoilersThe beginning of the end for Molly and Issa arrives, and maybe for Condola’s relationships with Issa and Lawrence as well.
Insecure: Season 4 Episode 2 “Lowkey Distant” – Recap/ Review (with Spoilers)As Issa gets closer to Condola, both Lawrence and Molly seem to think that relationship is becoming a problem.
Insecure: Season 4 Episode 1 “Lowkey Feelin’ Myself” [Season Premiere] – Recap/ Review (with Spoilers)“Insecure” returns, and it seems like the beginning of the end for Molly and Issa’s friendship.
Insecure: Season 3 - Recap/ Review (with Spoilers)
Insecure: Season 3/ Episode 8 "Ghost-Like" [Season Finale] - Recap/ Review (with Spoilers)
Insecure: Season 3/ Episode 7 "Obsessed-Like" - Recap/ Review (with Spoilers)
Insecure: Season 3/ Episode 6 "Ready-Like" - Recap/ Review (with Spoilers)
Insecure: Season 3/ Episode 5 "High-Like" - Recap/ Review (with Spoilers)
Insecure: Season 3/ Episode 4 "Fresh-Like" - Recap/ Review (with Spoilers)
Insecure: Season 3/ Episode 3 "Backwards-Like" - Recap/ Review (with Spoilers)
Insecure: Season 3/ Episode 2 "Familiar-Like" - Recap/ Review (with Spoilers)
Insecure: Season 3/ Episode 1 "Better-Like" [Season Premiere] - Recap/ Review (with Spoilers)
Star: Season 2/ Episode 2 "Insecure" - Recap/ Review (with Spoilers)
Insecure: Season 2 - Overview/ Review (with Spoilers)
Insecure: Season 2/ Episode 8 "Hella Perspective" [Season Finale] - Overview/ Recap (with Spoilers)
Insecure: Season 2/ Episode 7 "Hella Disrespectful" - Overview/ Recap (with Spoilers)
Insecure: Season 2/ Episode 6 "Hella Blows" - Recap/ Review (with Spoilers)
Insecure: Season 2/ Episode 5 "Hella Shook" - Recap/ Review (with Spoilers)
Insecure: Season 2/ Episode 4 "Hella LA" - Recap/ Review (with Spoilers)
Insecure: Season 2/ Episode 3 "Hella Open" - Recap/ Review (with Spoilers)
Insecure: Season 2/ Episode 2 "Hella Questions" - Recap/ Review (with Spoilers)
Insecure: Season 2/ Episode 1 "Hella Great" [Season Premiere] - Recap/ Review (with Spoilers)
Insecure: Season 1/ Episode 8 "Broken as Fuck" [Season Finale] - Overview/ Review (with Spoilers)
Insecure: Season 1/ Episode 7 "Real as Fuck" - Overview/ Review (with Spoilers)
Insecure: Season 1/ Episode 6 "Guilty as Fuck" - Overview/ Review (with Spoilers)
Insecure: Season 1/ Episode 5 "Shady as Fuck" - Overview/ Review (with Spoilers)
Insecure: Season 1/ Episode 4 "Thirsty As Fuck" - Overview/ Review (with Spoilers)
Insecure: Season 1/ Episode 3 "Racist As Fuck" - Overview/ Review (with Spoilers)
Insecure: Season 1/ Episode 2 "Messy as Fuck" - Overview/ Review (with Spoilers)
Insecure: Season 1/ Episode 1 "Insecure as Fuck" [Series Premiere] - Overview/ Review (with Spoilers)
Molly, Issa, Kelli, and Tiffany smoking on Issa's balcony
Insecure: Season 5/ Episode 7 “Chillin’ Okay?!” – Recap/ Review (with Spoilers)
Trajectory: Plateau
This felt more like a final season type of episode. It talked about characters we may never see again, had Tiffany mention her departure, and really pushed us to see how far the characters have come and acted as a reminder that we won't get to see what's next. We'll just be given an idea of what's to come.
Highlights
Co-Parenting – It Gets Better
When Accessibility Wanes, Accountability Becomes Paramount
Disputable
84

Subscribe to Blog via Email

Enter your email address to subscribe to this blog and receive notifications of new posts by email.

Follow Wherever I Look on Twitter and Instagram, Like us on Facebook, and Subscribe to the YouTube Channel.

Leave a Comment

* By using this form you agree with the storage and handling of your data by this website.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

This website uses cookies to improve your experience. We'll assume you're ok with this, but you can opt-out if you wish. Accept Read More