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Insecure makes some major changes in one of its best episodes yet

Issa Rae
Photo: Merie W. Wallace (HBO)
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We may be four episodes into this season, but “Fresh-like” would’ve served well as the actual premiere. There are major changes with shifts we’ve been waiting for Issa to take since season one. Issa’s journey to adulthood hasn’t necessarily been frustrating or prolonged, but she’s definitely moving at her own pace. “Fresh-like” forces Issa to gather some momentum. Still, these changes are very much linked to a man, so it’ll be interesting to see how she feels when the fireworks around Nathan have subsided. 


“Fresh-like” feels like the start of a new Insecure that’s no longer focused on world building and is finally telling Issa’s story. There aren’t any cultural or societal conversations in the subtext of Issa’s storyline, it’s just about her emotional growth. Issa’s relationship with We Got Y’all has often been used to dive into topics like racism in education and white savior syndrome, but that well has run dry. Issa is ready to move on and the decision to have her quit is bold and exciting for the show’s narrative.

It wasn’t like we didn’t see this coming. Issa bailing on her meeting with Frieda was the final blow. Being back in the field and possibly introducing music education aren’t even exciting opportunities for Issa at this point. Yes, Nathan is extremely cute, but if We Got Y’all was Issa’s real passion, I’d like to think she wouldn’t have bailed on Frieda. Even though it was childish for Issa to play hooky, she realized that and made the mature choice to quit. We’ve said bye to Daniel, We Got Y’all, and Lawrence’s mix cds–Issa is making strides and it’s refreshing.

Y’lan Noel
Photo: Merie W. Wallace (HBO)

I guess it isn’t fair to say Issa was entirely motivated by Nathan. Getting her own place has put Issa back into her zone. The episode opens with Issa rapping in front of her bathroom mirror. Rapping is an indicator of how comfortable Issa is with herself, her problems and her life. It’s what she turns to when things are stressful. She wasn’t able to open herself up like that around Daniel and now she’s glowing again. It’s only fitting that Daniel interrupts the moment, but Molly’s stern “Bye, Daniel” felt like a great send off. Daniel will be back, but I hope we get a nice long endeavor into Nathan before we get updates on Daniel’s Soundcloud career.


Since Nathan is new on the scene, he’s also helping us learn more about Issa. We know Issa has a brother, but the show has never really dove into her relationship with her parents or her childhood. Seeing Issa’s childhood home and the relative privilege she grew up in helps frame her character more. Issa still wants to be the cool, rapping, world-changing person she imagined when she was younger. The realities of adulthood don’t exactly line up with that. Holding onto this dream is holding Issa back and she’s finally doing something about it.

Molly is also doing something about her work predicament. Molly though transitioning to a mostly black law office would be easy. She complains to her therapist that it feels like she’s starting over. The thing is...she is starting over. Molly is also guilty of chasing a life she imagined rather than dealing with her reality. Molly thought this would be her dream job, without social politics or sexism. She quickly found out that wasn’t the case and now she’s scrambling to get what she thinks she needs to make up for this imaginary feeling of being “behind.”

Yvonne Orji
Screenshot: Screenshot (HBO)

Unlike Issa, Molly is quick to make changes when she’s unhappy with her situation. First, she tries to join in on “the woman thing” her fellow female coworkers seem to have. When she realizes joining forces with the firm’s hot shot male lawyer would be more beneficial, she quickly jumps ship. These choices will have repercussions for Molly and she’s not considering her reputation in her rush to achieve her goals.


Also...Molly hasn’t been completely honest with her therapist, which throws all of her maturity this season into question. She hasn’t told her therapist about Dro! Molly was out here with her rules and “are we friends or are we acquaintances who have sex?” ultimatums like she knew what she was doing! Turns out she’s been figuring this out on her own and her therapist may offer a different perspective.

Yvonne Orji (left) and Issa Rae
Screenshot: Screenshot (HBO)

Molly is still lonely and she hasn’t always made the best decisions when she’s trying to fill the emptiness she feels. I wouldn’t be shocked if she ends up sleeping with a coworker or someone else she shouldn’t be seeing (that includes Dro). The therapist asking about Dro was a clever reveal on Insecure’s part and tells us so much we haven’t actually heard Molly say. Molly is a more closed off character than Issa and these brief moments are a great glimpse into the stuff she’s hiding from herself.

“Fresh-like” isn’t just a great episode of Insecure, it’s a near-perfect summary of all Issa and Molly have been through since the series premiered. The episode dabbles in the surrealism that makes Insecure feel like nothing else on television and gives us an exciting change of pace. “Fresh-like” brings together nearly everything that works about the show in order to move the story forward. That’s a huge pivot from the ground the show has retread with Daniel and Issa so far this season. 


Stray Observations

  • Molly really came through on the housewarming gifts. I’m glad Issa doesn’t have to sleep on the floor like a little slave girl.
  • “You a brand new bitch! You a make no mistakes bitch!” As much as I want to believe this, I still think Issa is going to make some more mistakes.
  • Nathan is cute but...I don’t trust him. He’s too pretty. He’s from Houston. Boys with eyes like that just break hearts and lie.
  • I love Property Manager Issa. Trina and the squirrels in the wall are great. I also love Trina’s son. “What are y’all doing? Eating tacos and kissing on the mouth?” Children just KNOW. I hope we see more of both of them.
  • “They didn’t teach modesty at Morehouse.”
  • I kind of can’t believe that Issa would break into her old house and get in the pool, but Nathan has her doing all kinds of new stuff.
  • Chad! On the park bench! I hope we get to see him return in 3D form.
  • “My momma had said to wait.”

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About the author

Ashley Ray-Harris

Ashley Ray-Harris is a stand-up comic and writer.