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Natasha Rothwell directs Insecure’s funniest episode

“Tired, Okay?!” highlights everything about Insecure that will be missed when the show is gone.

Natasha Rothwell directs Insecure’s funniest episode
Issa Rae (left), Kendrick Sampson Photo: Merie Wallace/HBO

Insecure has always been one of HBO’s funniest shows, but that can often be forgotten in the midst of the show’s focus on character development, relationship drama and character dynamics. Of course, Insecure always has jokes, but gags like Kelli peeing herself at Coachella haven’t had a place in recent seasons. “Tired, Okay?!” is a near perfect example of Insecure when it leans into both comedy and emotional growth.

From the moment Issa throws Lawrence’s baby and Flo Milli starts playing, this episode cemented itself as one of Insecure’s funniest. Is it any shock that it was directed by Natasha Rothwell? Rothwell brings a Kelli-like sensibility to Grace Edwards’ script that only makes the episode’s moments like Molly Time and Issa’s quest to get Nathan to say “I love you” even funnier. Rothwell knows you don’t quite know what to expect from these characters: Issa very well might walk up to Lawrence and Condola to talk, even though that’s a horrible idea. Molly might make the mistake of sleeping with her boss on a work retreat.

With Issa, the reveals are more focused on her own imagined actions. Seeing Lawrence and Condola doesn’t actually make her want to harm a child, but it is enough to send her Instagram-stalking Lawrence, where we learn he has moved back to Los Angeles. This doesn’t necessarily mean Condola and Lawrence are back together, but of course Issa imagines the worst when a vision of Condola thanks her for giving up on Lawrence. The long stroke Issa liked? Even longer and Issa is suddenly realizing she might’ve been wrong to rush into things with Nathan.

Certainly, it isn’t a great sign for your current relationship if you’re daydreaming about your ex’s babymomma, but Issa refuses to connect the dots. Instagram-stalking Lawrence doesn’t lead to her carefully considering what she really wants, instead she has the most awkward sex with Nathan where she tries to trick him into saying he loves her. Even if it just means he loves how she rides him. Nathan and Issa aren’t in love, but Issa wants to be in love. She wants the stability she had with Lawrence and Nathan isn’t that person at all. Rather than focus on building a new relationship, she’s slotting Nathan into the old one. Either way, their relationship isn’t at a place where they need to be making long term commitments.

Issa is being inconsistent! Not just in her love life, but also with her career. I was hoping the Crenshawn storyline wouldn’t be done and this week Issa confronts him. Well, she brings “olive branch” brownies and talks around Crenshawn’s issues. Crenshawn was inspired by Issa to do things for the community and Issa is clearly starting to get more focused on press and brand collaborations. I wish we could’ve seen some of the earlier scenes between Crenshawn and Issa to really understand how she motivated him, but we’re left to take his word for it. Issa is defining her own career now, but she could lose herself in the hype.

Last season, I doubt I would’ve suggested that Issa take advice from Molly, but Molly is really doing a good job on her New Molly transformation! Yes, she’s still taking on too many responsibilities and not opening up to the people around her, but she does a little bit this episode! Maybe she didn’t mean to get wasted in front of her coworkers, but letting them see Molly Time was necessary. It’s good to see that Molly is at a place with her coworkers where they can make jokes and admit that they didn’t always rock with each other.

Does that mean I like the sexual tension between Molly and her coworker, Taurean? Honestly? Yes. Absolutely yes! Molly needs someone who understands her work life! Molly and Taurean haven’t always got along, but I like the competitors-turned-lovers narrative of it, even it feels a little rushed. The “I like mugs”/“My mom had a mug” conversation (which was improvised!) was such a cute start to a crush that I simply must support this relationship.

“Tired, Okay?!” highlights everything about Insecure that will be missed when the show is gone. The episode finds new character dynamics and introduces Molly and Issa to new journeys. Rothwell and Edwards have crafted an episode that builds excitement as we enter the back half of Insecure’s final season.

Stray Observations

  • I am so sorry for the late review! A burst pipe left my laptop (and review) on rice!
  • Molly’s mom woke up! But I really couldn’t believe she still went on that retreat and didn’t take more time off of work!
  • I hate the way Nathan said “I like the way you ride me” and I don’t really care about his barbershop drama. There are plenty of other places in Los Angeles where he could work, so it only hits on how flaky he is that he has a problem and immediately wants to move.
  • Issa, do not ever try to make a man say he loves you during sex!!
  • I worry Issa is going to try and get Lawrence back. I don’t want her to be a stepmom.

 
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