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Issa Rae
Photo: Merie W. Wallace (HBO)
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This was a difficult episode of Insecure to review. As a standalone episode, it had some of the show’s most hilarious moments of the season. But, when you examine “Obsessed-Like” against the show’s entire third season things start to fall apart. This is the penultimate episode and there’s no real momentum taking us into the finale. It feels as though the season is just getting started. “Obsessed-Like” would’ve been great as a fourth or fifth episode, but at this point, it’s just odd that it took us so long to get to this point.


Why did this season spend so much time with Daniel instead of just developing Nathan as a character? That would’ve given his ghost more impact, but since we only knew Nathan for about 3 episodes, he always seemed like a sketchy character doomed to hurt Issa. Nathan’s disappearance isn’t shocking, everything about Nathan screams “imaginary dream boyfriend fuccboi.” Still, Issa’s heartbreak did feel real. Issa’s internal monologue worked as a great narrative device that perfectly captured the 4 stages of getting ghosted: hope, thirst traps, going crazy, and, finally, acceptance.

The first half of the season focused on the history between Daniel and Issa that doomed their relationship. Nathan gave Issa hope because he was detached from her past and inspired her to do make some major changes. Issa wanted Nathan to be the person she needed to reach her glow up, but in the end, he’s just not that person. Nathan’s disappearance doesn’t just hurt Issa because she’s lost a potential relationship, she’s also lost everything he represents: a new beginning and exciting opportunities.

Alexander Hodge (left), Issa Rae, and Yvonne Orji
Photo: Merie W. Wallace (HBO)

Nathan encouraged her to start the block party. Nathan inspired her to quit her job. He was there for these monumental changes she went through, but that doesn’t mean he should get credit for them. This season, Issa started taking on her problems on her own and once she realizes that, she’ll be able to move on. Deleting his number is a good start, but her reunion with Lawrence could spell disaster.


After spending a week wallowing over Nathan, Issa finally gets out of bed and goes to the entrepreneur workshop Lawrence recommended. That’s great! If Issa wants to take this block party thing seriously, she needs to get organized. And yes, Issa has just suffered a huge breach of trust and Lawrence is someone she turns to when she’s hurt, but it’s starting to feel like Issa relies a bit too much on the men in her life to get her shit together. It was great to see Issa and Lawrence back together and it would be wonderful to see their relationship become a friendship, but this had romantic overtones.

Jay Ellis
Photo: Merie W. Wallace (HBO)

That being said, Lawrence has proved his worth to Insecure. His reappearance is a big reason why the season finally feels like it’s getting started. The show is using Lawrence to explore some interesting topics and it would be great to see how that develops outside of his involvement with Issa. The black church scene was absolutely perfect and the show would do a great job taking on the church and the hierarchy of dating within it. Lawrence has already hit it off with someone, but religion would inevitably be a sore point between them. It would also be interesting to see how Lawrence approaches dating someone who may be more traditional in their beliefs.

Molly’s plot was also satisfying, even though it got a little ridiculous. I like that Andrew isn’t afraid to call Molly out and doesn’t put up with her games, but I would think that includes telling her to leave after she shows up unannounced. The height of Issa’s obsession was definitely captured when she went through Nathan’s room (no, Issa, his password is not your name), but it just seemed too out of character for Molly. Molly doesn’t typically enable Issa to this extent. She gives her great advice when she tells Issa to move on, so it’s odd that she’d indulge Issa’s request. Molly is killing it at work though, so maybe she just felt like she needed a little excitement this week.


With one episode left, it doesn’t feel like too much has really happened this season. Did we really need Issa to give Daniel another try if she could just write it off as “sleeping on people’s couches” when she talked to Lawrence? Did we really need to care about Daniel’s SoundCloud career? Why hasn’t Molly really exposed her feelings on her relationship with Dro? There are a lot of questions as the finale approaches, but none of them have simple answers.

Insecure still veers wildly between being a static “hangout” show and having an evolving narrative. Most of the time, it can find a balance between the two, but this season hasn’t felt particularly committed to either side. 8 episodes isn’t enough space to explore a lot of the stories this season hinted at. The finale has a lot of work to do to tie these threads together. It better not end with Nathan magically showing up like we’re still supposed to care about him after this.


Stray Observations

  • Chad getting up to join the congregation was absolutely perfect. There’s always that moment when you’re like “is anyone taking this seriously?” only to see your friend/family member running down the aisle.
  • I wonder if Lawrence found a Pick-Me. I’d love to see Insecure’s take on that whole thing.
  • I feel for you, Issa. We’ve all been there. Well, not exactly, I’ve never tried to break into someone’s computer.
  • I just want Lawrence and Issa to be friends.
  • I wish we could see Molly open up about Dro. Did Dro make her think their relationship was more than it was? Less than it was? Molly was upset with Dro when he dismissed her boundaries, but what promises did he make?
  • Next week is the finale! This season flew by!

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

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