Hey yall,

Hope you had a great weekend!

We’re doing something a little different this week. I’ve been talking yall’s ears off about Insecure, but it’s because I want to make sure we give our flowers to an iconic Black show that with each season proves that “regular Black women” matter too. Back in the day, we had an abundance of Black TV shows that documented the lives of regular low-middle income Black characters, like A Different World, Moesha, and Sister, Sister. That golden era of Black TV sitcoms is long gone, but Insecure continues that legacy and is one of the last standing TV shows that we collectively watch each week as a culture. Also, it’s the final season and I hate that for us!

If you haven’t been keeping up with season 5 (and haven’t been joining our weekly Insecure Twitter chats on Mondays at 5pm PST 👀), I tapped writer Demilade Adebayo to give you the ultimate recap; full of her personal takes on situations Issa, Molly and crew have found themselves in and songs that match each episode.

Feel free to leave a comment below or hit reply if you are or aren’t a fan of this type of content. We’ll be back with more carefree stories next week!

Take care,
Anayo Awuzie
EIC of Carefree

Episode 1: Siri, play Single Again by Trina!

Okay, okay, let me not jump the gun. If you have watched Insecure’s Season 5 opener, you know exactly why I started off commanding Siri to play the iconic Trina record. The episode, Reunited, Okay?!, starts off with our four favorite girls and husband, Derek, taking a trip to their alma mater, Stanford, for their ten-year class reunion. Tiffany delivers the update on our two favorite girls while chatting with her husband and Kelli on their car ride down to Stanford. Molly is still down bad after her breakup last season with Andrew. Issa is still messing with Lawrence, despite his pregnant ex, Condola (Condolences, Condominiums, Constellations, etc., to the masses). And the relationship we should care about the most, the one between Issa and Molly, still is not entirely repaired after last season’s blow-up.

Although their relationships are rocky, my girls, Tiffany and Kelli included, seem to be doing well individually. Since last season’s block party, Issa has launched her company, The BLOCC (Black Life Opportunities Culture and Connection). Its success has garnered attention, landing her on an entrepreneurship panel during the class reunion weekend. Molly shows a semblance of emotional maturity. She relates her therapist’s advice to situations several times within the episode. Tiffany seems to be in a much better space than she was last season, delivering her shady one-liners with care and love, of course. And Kelli, who is accidentally ascended to the heavens by her alma mater (obituary and all), still serves the best, undeserving vibes.

There is a general theme of reflection throughout the episode. Ten years after graduating, things are not as planned. Issa isn’t a big-time lawyer. We found out that this was Issa’s college goal during one of Issa’s infamous mirror talks featuring a brace-faced college-aged Issa. Molly laments her failed relationships. At the reunion, she reunites with an old fling who is newly divorced and still into her. She almost goes into Molly mode, overthinking and analyzing the situation but checks herself, reminding herself what happened when she did that in the past. And Kelli also reflects on this episode. The college’s accidental declaration of her death makes her think about the way people see her. She is not satisfied with the memories her classmates shared of her. I personally want to fight the person who remembered her for always carrying a purse. Kelli is left wondering if she was to actually pass what her impact would be.

What is great about this episode is that although they are not where they thought they would be, the ladies are alright (shoutout to Chloe x Halle). Issa sits on the entrepreneurship panel and admits that she still does not really know what she is doing. She beautifully relates the idea that there will be a definitive moment where you make it, and everything will fall in place and make sense is a myth. Ten years later, all the ladies are still unsure what they are doing and why, and that’s okay! Issa has a promising business that has so much space to grow. Molly may not have the relationship she wants. But therapy has given her the tools to excel in her next one. And though Kelli might not be remembered in the greatest light by her former classmates, her real friends love and appreciate her in a way only people close to you can.

By the time they are leaving the reunion, things feel better for everyone. Issa and Molly are a little closer after Molly initiates a conversation asking Issa if they’ll be okay. That conversation is strengthened by an incident where they hilariously get robbed by a former classmate. If nothing draws you closer, a robbery might.

Although this episode was most satisfying for me as a viewer, I almost lost it at the end. Now we can get into the moment that prompted me to summon Siri at the beginning of this episode recap. Issa flies home from the reunion, and who else but Lawrence is there to pick her up from the airport. I was not thrilled to see the two together as a couple. Fortunately for me, the vibes between Issa and Lawrence were way off. Something about the reunion put things in perspective for my girl Issa. By the time Lawrence was pulling off after dropping Issa off at her place, the two were officially over. The breakup was beautifully nondramatic, quick, calm, and seemingly mutual. Although I am not and have never been Lawrence Hive, I felt for him, we didn’t see much of Lawrence this episode, but I’m sure he has been reflecting as well since we last saw him with the baby coming along and all. I’ll admit I did say damn to myself when he accepted Issa’s decision to move on. With that being said, my girl Issa is single again!

Episode 2: Siri, play Stay the Night by Mariah Carey!

While we focused on the past in the season opener, Season 5 Episode 2, Growth, Okay?!, takes us into the future. The BLOCC is hot (so corny when I say it), but really, Issa’s business baby is doing very well. Issa is booked and busy. She and her assistant Quoia, who I have so much respect for, assistant life is no joke at all, run around much of this episode handling different BLOCC events. Nathan is back, and Issa helps him plan an event for the first anniversary of his shop opening. A business date between the two about the event starts feeling very romantic. I swore I heard wedding bells! Issa and Nathan keep it cute and just discuss business.

Molly is doing her over in Mollytown. Molly debuts a lovely new haircut, and we experience a montage of things going well for her. She finally has found her groove at the law firm she works at. She is adamant about focusing on herself and being there for those around her. Molly spends much of this episode trying to convince her parents to get serious about planning their estate. Her mom instead rather try to hook her up with an old-faced trap music converting pastor. Molly is not here for the pastor but does ponder going back to the dating scene. The idea of doing so pushes Molly to do some serious introspection, which we get to see via flashbacks of Season 1–4 (Molly’s dating life has been a ride). As a unit, Molly and Issa are back good again. Thank God! The episode is full of Issa and Molly text messages (with GIFs!), dinner dates, and sleepovers. Both Issa and Molly are both handling their business in blue at that!

Handling business is not easy, and both Issa and Molly are put to the test of doing so. The Blocc has taken on the task of putting on a fashion show in Crenshaw. Issa has chosen to showcase a designer, Crenshawn, played by Kofi Siriboe. Unfortunately, the company, NBW, that Issa is partnering with has assigned her two company representatives who disagree with her choice to showcase Crenshawn and request that she consider a more experienced designer. Issa takes advice from Molly and decides to speak directly with the boss at the partnering company to see if she could get them to understand why Issa chose to showcase the particular designer. The two have back and forth about the show’s vision and Issa, who in the past has backed down from difficult conversations, defends her stance, ultimately getting the company to back her plan. Crenshawn can stay but not without having their notes and requests of how the show should go, of course. Issa delivers the notes to Crenshawn, who is not here for NBW’s new vision. While Issa successfully defended herself, she was unsuccessful in defending Crenshawn, providing notes that would undermine his vision. Crenshawn sticks to his artistic gut delivering a successful show the way he envisioned it.

Issa is left feeling bad as she honestly should. Issa reaches out to Nathan, and the two hang out for the evening. When it gets late, Issa suggests that he doesn’t go. I thought that my favorite pair would finally make something happen, but Issa ends up crying while Nathan kisses her. He consoles her until Issa falls asleep and ends up dipping sometime during the night. Issa’s night with Nathan did not go quite like the Mariah Carey song, but I still have hope for the two.

Episode 3: Siri, play The Pressure by Nas!

This one may seem on the nose, but I picked the song before realizing the title in my defense. Season 5, Episode 3, Pressure, Okay?!, is all about Lawrence’s life post-Issa breakup. Lawrence has moved on. The first minutes show Lawrence in his element. After leaving Issa’s place, he walks into a home full of boxes indicating that he’s made a move. He has a new job in which he is really confident and even finds himself on a little date.

I tried to be happy for Lawrence. I really did, but something was not sitting right with me. I saw his new home, his new job, possibly his new girl, but then I thought to myself, if Lawrence is in the same timeline as Issa and Molly a year after the breakup, where is his new baby! Insecure writers delivered because I screamed when Lawrence found out his baby was born through a text, but we’ll get to that later, in the middle of his date. This is where the drama begins. This episode is full of baby daddy blues. Condola has the baby earlier than expected, leaving Lawrence rushing to the hospital in a first date suit. When he gets there, he meets Condola, her sister played by Keke Plamer and her mom played by thee Lela Rochon, and his son Elijah Mustafa. He apparently has ears as big as Lawrence. Big-eared babies are the cutest, though.

Condola and Lawrence have no plan of effectively co-parenting their child. Condola wants to figure everything and inform Lawrence of things after she’s done so. And Lawrence says he intends to be as involved as possible but wants to process to be easier than co-parenting actually is. When he texts Condola canceling his trip to see his son because he was tired, I had to pause the episode and say, relax, relate, and release to myself. Things honestly just get more intense throughout the episode. Lawrence, Condola, and Elijah all get invited to Tiffany and Derek’s daughter’s first birthday. I know Lawrence and Condola want to be a united front for their child, but I wished one of Elijah’s parents had decided to stay at home for the occasion. The two have a blow-up over Lawrence introducing him to solid foods without consulting Condola. Luckily for Lawrence, Derek was there to intervene and impart necessary advice to Lawrence reminding him to not let his personal feelings get in the way of being the father he needs to be.

The most moving part of this episode was the split-screen showing the day in the life of Lawrence and Condola. It was the perfect setup for Condola’s last-minute decision to not allow Lawrence to take the baby overnight. Even if you disagree with Condola, it’s hard to not understand where she is coming from. In any facet of life, it is hard for anyone to impart responsibilities to someone who has not put in the work to have the experience necessary to complete the task. When the job is ensuring a child’s safety, I’m sure the bar is raised much higher. The blow-up over Condola’s choice is the episode’s worst. With Lawrence even alluding to possibly taking Condola to court for child rights. On his flight home, Lawrence’s plane experiences horrible turbulence. Turbulence putting everything into perspective for Lawrence is so relatable. Turbulence will have you second-guessing it all. By the end of the episode, an apology is exchanged between Lawrence and Condola. There are no solutions proposed, no idea of moving forward or where to go next, but there’s the acknowledgment of things needing to change.

Episode 4: Siri, play Finally by Toni Braxton!

Whewwww, this week’s Insecure episode is most definitely Top 5. I will always be here for fine black people frolicking in the sun having a good time. This week’s episode, Faulty, Okay?!, takes Issa, Molly, and Kelli to a beach party to celebrate the first anniversary of Nathan’s barbershop. Each one of the ladies arrives with different energy. Kelli’s spiritual journey is going strong, Molly is living her best carefree life (I want a Molly moment tbh!), and Issa has A LOT going on. She has not cleaned up the messes she made from episode 2 of the season. Crenshawn, the designer she worked with on the showcase, is coming for her and The BLOCC hard on Twitter and the kissing to crying moment with Nathan has not been addressed or mentioned by either one of them.

Issa may be moving away from being Insecure this season, but the awkwardness is still alive and well in her. Nathan feels a way about how things went between Issa and him the last time they were together. He was so standoffish to Issa that I was almost sure the episode would end with Nathan doing Issa how she did Lawrence at the end of the first episode of the season. If you weren’t sure if Issa liked Nathan before this episode, it’s clear that she feels something as it progresses. She gets a little jealous when she notices Nathan interacting with Resha, a hairstylist that works in Nathan’s shop. Issa gives us some Molly-level paranoia, coming to the conclusion that Nathan and Resha must be having relations with one another. Molly, like a true friend, asks Resha what is up with her and Nathan. The answer is nothing at all, giving Issa relief.

An earthquake takes the anniversary celebration from the beach to a local bar. Had it not been for Molly auditioning two of Nathan’s barbers for a nighttime recap and Kelli’s weird spiritual breakthrough with Resha, Issa would’ve been on her way home. Thank God for Molly and Kelli’s extracurricular activities because Nathan and Issa finally discuss the teary late-night moment at the bar. A breakthrough between the two is interrupted when Nathan’s cousin Thomas and his wife Velma show up at the beach-turned-bar anniversary celebration.

If no one tells your business, your family will. Thomas and Velma are quick to mention Nathan’s wild past, throwing little jokes and jabs his way when the opportunity allows for it. Nathan is clearly uncomfortable with it but does not say much. However, if looks could kill, Velma would be dead several times over. Something is off between the two. I felt bad watching her try to insert herself while Nathan and Thomas chop it up, she seems nice, and her braids are cute. She also encourages Thomas to go to a party (thrown by Jason Derulo) with Nathan, Issa, and the crew despite Nathan’s attitude towards her.

The party ends up being a bust after the crew discovers that they are not Hollywood to get enough to get in. Molly’s plan to sneak everyone in through a backdoor offers a moment of honesty between Nathan and his cousin. Thomas is uncomfortable with the backdoor plan. Nathan blames his cousin’s hesitancy on his wife. This prompts a conversation about a past situation where Nathan was asked to stop living in their home because of his erratic behavior. Nathan always assumed that it was Velma’s choice, but Thomas finally admits that it was his and that his wife graciously took the blame for it for the sake of the familial relationship. Thomas heads home, leaving him with this revelation.

While everyone else is off sneaking through a backdoor, Nathan reacts to what Thomas admitted to him and who else is there to help him make sense of it than Issa. Nathan reveals that he was manic while staying with his cousin, and his wife has never told them that. He assumed that their opinions of him would change once they saw the success of his shop.

The conversation about Nathan and his cousin evolves into a discussion about Nathan and Issa. ISSA FINALLY TELLS NATHAN THAT SHE WANTS TO BE MORE THAN FRIENDS. Nathan agrees with her position. The earth literally shakes as Nathan and Issa finally move out of friend zone territory.

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