TV / Insecure

'Insecure' Season 3, Episode 7: Obsessed-Like

. 8 min read . Written by Lindsay Pugh
'Insecure' Season 3, Episode 7: Obsessed-Like

"Obsessed-Like" is directed by Kevin Bray, written by Prentice Penny. Bray has been involved with "Insecure" since S1 and has worked on many other dope shows like "Black-ish," "Fresh Off the Boat," and "The Americans." He got his start directing music videos for icons like Jennifer Lopez, Lauryn Hill, and Celine Dion (nbd) and has directed films and commercials. Why hasn't anyone done an in-depth interview with him yet? It seems like he's had a really interesting career. HBO put together a nice POV episode with him and production designer Kay Lee. I know I've mentioned it before, but all of the HBO behind the scenes content is top-notch:

Prentice Penny is the "Insecure" showrunner and usually writes and directs a few episodes each season (he directed S3E1 "Better-Like"). He's also always a part of the "Wine Down" features after each episode with Issa Rae. I'm not on Twitter much, but I recommend following him there if it's a social media platform that you use. He often answers fan questions about the show and is spot-on with his gif responses.

The next time people ask me why I'm not on social media more, I'm just going to point them to this episode. Even without the burning desire to find out why some dude wronged me, I find social media to be a major time suck and toxic wasteland of misinformation. It's easy to become obsessed with what other people are doing and to feel ignored and worthless in comparison. Why bring that negative shit into your life? If I were still single, I would have definitely deleted all of my profiles by now.

I remember going on Tinder dates and reeling when I felt like I had a good time with somebody and then never heard from them again. I would then find them on IG and make up reasons why they hadn't gotten in touch. It was pathetic and stupid, but even though I was aware of how sad it was, I couldn't stop myself. The dating scene is ROUGH, especially in big cities where people are busy and perpetually dissatisfied. It's easy to turn into an Issa, obsessing over someone you had fun with a few times but haven't heard from since, or a Molly, shutting everyone out because you've been disappointed too many times. I want to take Issa by the shoulders and shake her and then give her a hug because I know how shitty it is to feel rejected by someone who initially seems supportive and kind.

"Obsessed-Like" opens with an overhead pan of Issa sleeping in bed. As her eyelids slowly flutter, we see the ceiling come in and out of focus, as if from her POV. As she jolts awake, a voiceover tells us what she's thinking:

"These dreams are so weird. Why am I always losing my teeth? I need to look up what that means. What time is it? Ooh. I forgot to eat these [Raisinets]. I'm hungry. What day is it? Really, Nathan? A whole-ass week? Fuck that."

The rest of the episode continues in the same fashion. Issa goes through the motions   while continuing to obsess over Nathan. She's glued to her phone, looking at it immediately after ever buzz, perpetually hoping that it's him (but instead it's just a Taye Diggs IG follower alert and Bible verses from her mom). The teeth dreams persist, and her anxiety reaches a fever pitch when someone tags Nathan in an IG photo and thanks him for the haircut. Confirmation that he's not dead sends Issa into a rage spiral and so she grabs her keys, says "fuck it" to her outfit of pajamas, grabs Molly, and drives to Nathan's house.

As Molly says, "Girl! What is you doin'?"

The fact that Molly goes agrees to this shit says a great deal about her friendship with Issa. Nathan lives with Andrew, the dude Molly met (and embarrassed herself in front of) at Coachella. Earlier in the episode, Molly has a nice brunch date with Andrew that seems to go well. They joke about where they're from and she's actually real about why she avoided him post-festival:

Andrew: So why'd you dodge me for so long?
Molly: Honestly I was embarrassed by Coachella.
I was doin' the most, and you didn't need to see all that.
Andrew: Well, maybe that's a good thing. We don't have to pretend with each other.

These two seem good together and I'm happy that Molly lets her guard down enough to enjoy Andrew's company. Although she has to leave brunch early to get back to work, they make plans to meet up the next day. Sadly, things deteriorate rapidly during their next date. During one of their flirty/jokey exchanges, Andrew takes things too far and Molly handles it poorly:

Molly: But you know what else I remember? You telling me how you kissed your boy's girlfriend.
Andrew: OK.
Molly: Grimy.
Andrew: Oh, says the girl who hooked up with her married friend? Mm-hmm.
Grime recognize grime.
Molly: I'm not grimy, and you don't know the situation.
Andrew: OK. Tell me the situation.
Molly: Um, he led me to believe it was something it wasn't.
Andrew: A married man led you on? Wow. [Laughs] Come on.

Molly doesn't take kindly to being questioned like this and ends up leaving Andrew at the bar with barely any explanation. I don't like how he laughed at her and gave her a hard time after she started to get defensive, but Molly should have handled this better. He doesn't know the situation or the fact that it was recent and she's still not over it. He apologizes when she gets mad and tells her his intention wasn't to upset her. She should give him the benefit of the doubt instead of jumping down his throat and punishing him for something that was truly an accident with no intended malice.

I don't know that I can support this much jewelry on anyone, man or woman.

When Issa forces Molly to show up at Andrew's door with apology desserts as a fake excuse so she can snoop on Nathan, it's after all of this has happened. Andrew understandably responds with confusion and suspicion, especially when Issa immediately claims to need the restroom and ignores the one on the first floor in favor of the one near Nathan's bedroom. While Molly awkwardly talks to Andrew, Issa continues to fall down the crazy/obsessed rabbit hole. After entering Nathan's room, she convinces herself to look in his drawers, his trash, and finally, his computer. Thankfully, this dude is smart enough to use a password, but that doesn't stop Issa from guessing. After trying "Houston" and "Issa" 🙄 Molly finally comes to collect her.

What I like most about Molly and Issa's friendship is that even though both women might flounder in their respective love lives, they still manage to give decent advice to each other. They also don't have a problem expressing vulnerability, which is a sign of closeness they rarely exhibit with men. When Issa admits that she can't get over Nathan because he made her feel like something other than a fuck-up, my heart breaks for her. Issa needs to get her confidence back. Once she starts believing in herself again, she won't be so dependent on outside validation from some guy. She needs to be her own cheerleader, to find independent motivation to become a better person. Issa is, and always has been, her own worst enemy.

When she meets up with Lawrence after the entrepreneur workshop he recommended, I worry that she'll backslide, especially now that he's acting so supportive and Nathan is out of the picture. I don't care that Lawrence is back and I am interested in his story arc, but I don't want it to involve Issa as anything other than a friend.

While the church/religion flirtation was fine for one episode, I hope that's another aspect that doesn't carry over to S4. In an attempt to better himself, we see Lawrence attend service at a corny-ass church with a pastor who obviously tries way too hard to relate to milennials. Chad buys into it 100% (or pretends to in order to get pussy - tbd) and the woman Lawrence talks to after the service seems to find it valuable, but he isn't convinced. I guess I'll stay patient and see where this goes, but I hope Lawrence finds something else to inspire him to better himself because religion is bullshit (sorry, I can't help it).

Q: Does Lawrence get more attractive with each season? A: Yes.

One other notable aspect of this episode that I haven't touched on yet is Molly's office drama. She and Taurean had been working on a case presentation together but he called to let her know that he needed to postpone it due to an expedited hearing. This is how the conversation goes:

Molly: Will you still be back in time for our presentation?
Taurean: Not sure. I need to postpone it.
Molly: Postpone it? I just found the perfect precedent for the case.
Taurean: That's great, but I want to look at it first.
Molly: Sure. No problem.

It would have been easy for Molly to tell him that she wanted to move along with the presentation in his absence. She could have said, "Hey Taurean, we worked hard on this presentation and I don't think it's necessary to postpone it. I'm going to walk the partners through everything in your absence, but I'll make sure to give you credit where it's due." When dealing with corporate douche bros, I've found that I'm most likely to get my way when I tell them what I'm doing instead of asking. If Molly went with this approach, at least she would have looked like an honest, pragmatic person instead of a sneaky bitch. Even if Taurean said he wasn't cool with her giving the presentation solo, she could have informed him that she wasn't asking for his permission but wanted to keep him apprised of her plans.

I understand why Molly didn't do this, though. She's probably so used to Taurean interrupting and patronizing her that she assumed she had no choice but to acquiesce. I don't think Molly planned to give the presentation without him until the opportunity fell into her lap. It's not like she told Taurean "no problem" on the phone while secretly planning to screw him over the next day. The decision was spur of the moment, not premeditated. I don't mean to suggest that what she did is totally chill ... just that shit happens and if the situation were reversed, Taurean wouldn't apologize. While one part of me is like, "Oh, Molly ... you should do better," the other part is like "Women make 80 cents on the dollar, so fuck this dude."

Random observations:

  • Unfortunately, I think Issa's "Love is Al Green" shirt is vintage. I saw similar versions on eBay, but her exact white baseball t.
  • Issa's wardrobe might be $$$$ but gf still has a cardboard box for a bedside table, which I respect.
  • The best part of the episode is when Issa goes to the grocery store and casually steps over a crying child in one of the aisles. It is a perfectly executed sequence and I re-watched it at least 10 times.
  • The shared stalker IG account password is "slapahoe64."
  • I died a little when Issa accidentally messaged Nathan from her legit IG instead of the stalker account. Technology snafus are the worst.
  • My favorite song of the episode is "Clickbait" by TT the Artist & Mighty Mark. It plays when Issa posts a thirst trap selfie (and then is promptly called out by her brother).
  • This week's "Wine Down" features Kendrick Sampson (Nathan). Is it just me, or do he and Issa Rae have better chemistry IRL than on the show?