How Insecure Reminds Us of the Shitty Decisions We’ve Made (and Are Still Making)

HBO screenshot
HBO screenshot

If you’re one of those people who tune in every week to watch Insecure because Issa, Molly and Lawrence remind you of yourself or friends of yours, then last night’s episode did one of two things: It reminded you of all the dumb mistakes you’ve made when dating, or the characters reminded you of that one friend who doesn’t want to listen.


Let’s start with Issa, who seems to be gracefully transitioning into her self-proclaimed ho phase. The episode starts with her going to see Daniel for a round of midday sex, then later getting overdressed for a date with a Spanish guy she matched with on Tinder. While on said date, Daniel texts her to see if they can see each other again later that evening. But because Issa is trying to add “Spanish bae” to her ho-tation, she tells Daniel to pump his brakes.

The next day, Issa’s sexting neighbor bae (the guy she hooked up with two episodes ago) while driving to Daniel’s, causing her to rear-end a truck. The damage to her car is significant, but Issa also seems to suffer brain trauma. I say this because when she tells Daniel she’s gotten into an accident, he wastes no time coming to her aid. Daniel tells her that he’s got her back and instead of being grateful for Daniel’s chivalry, Issa reminds him that the thing between them is just casual and nothing serious.


That in and of itself is not a stupid thing to say. We all know Issa has been trying to avoid feelings all this season, but Issa’s timing could not be worse. Daniel clearly likes her, and while that is not a good-enough reason for anyone to choose someone, Issa needs to realize that even the people we are casually fucking deserve some level of courtesy. That moment just wasn’t the moment to remind him they’re just fuck buddies.

Molly also doesn’t seem to know when to let something go or ever realize that some things just aren’t about her. During her parents’ vow-renewal ceremony, Molly learns that years ago, back when she was too young to be worried about grown folks’ business, her dad cheated on her mom. Molly is wrecked by this news, calls out her parents for not being the couple goals she always thought they were and storms off in tears before the ceremony begins. It’s a very on-brand moment for Molly and a reminder that she probably ended her therapy sessions prematurely.

The moment is also a setup for her to finally go all the way with Dro, Molly’s childhood friend in an open marriage who propositioned her in last week’s episode. When Molly is leaving the house, Dro follows her to offer his comfort and capitalize on Molly’s vulnerability. This, of course, works because again, Insecure is a show that likes to tell us about ourselves, and who among us has not been either Dro, the shameless opportunist, or Molly, the woman who is still a victim of the condition her therapist calls “magical thinking”?

The last person in line to pick up a bottle of self-destruction is Lawrence. Ever since we saw Lawrence last week after his mediocre threesome performance sitting in his car outside the apartment he used to share with Issa, we knew the Lothario he wanted to be was about to morph back into the hurt man he actually is. While going through the process of jury duty, Lawrence scrolls through his Facebook feed and comes up on a picture of Issa at a party standing next to, of all people, Daniel, the man she cheated on Lawrence with. Now Lawrence is in the pursuit of answers because he assumes there’s more to Daniel and Issa than he ever knew. To get those answers he calls on Derek, which is a good idea only in theory.


Derek doesn’t really have any answers, but he sure does have a piece of wisdom for Lawrence to chew on, which is that maybe Lawrence had a role to play in Issa’s cheating. Derek suggests that Lawrence being unemployed for two years left the door open for another man to catch Issa’s eye. For many people who watch the series, this was the type of tough talk they had been wanting Lawrence to hear, but when I saw this, I chuckled in disappointment at not only Derek’s assertion but Lawrence seemingly buying it.

For one, Daniel as a character is a music producer. Why we would assume he is a successful one and a postcard of stability that Issa needs is beyond me. The other issue with Lawrence seeking out Derek is that Derek clearly doesn’t know much about Issa and Daniel’s relationship. He, just like Lawrence, doesn’t know that Daniel wasn’t just some random guy Issa met at the club.


Not only have Daniel and Issa been friends for years—but Daniel always had the sauce to make Issa blush, and Lawrence wasn’t going to be able to stop that even if he had a job or remembered her birthday. Derek’s suggestion that Lawrence had any control over Issa’s actions says less about what he knows happened between Lawrence and Issa and more about what he thinks of men with no job.

Of course, since Lawrence is emotionally lost, he takes Derek’s suggestion as gospel instead of going to the one guy who has consistently helped him through this difficult time, Chad. But such is life for Lawrence, Issa and Molly, three people who continue to hope that other people will help them clean up their messes: three people just like us.

Jozen Cummings is a senior manager at Bleacher Report. He is the founder and creator of the blog His work has been featured at, Deadspin, and many other publications.

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Cate Young

Umm, you are a LIE good sir. Derek’s point isn’t that Issa gets a pass because Lawrence was a bum, but that he needs to recognize that he isn’t blameless. Wayward dick isn’t the only way to hurt someone in a relationship. Lawrence was guilty of neglecting her LOOOOOONG before she cheated. Should she have just broken up with his ass and run off with Daniel? Yes. Was it shitty to cheat on Lawrence? 100%. But Lawrence doesn’t get to act like he’s not the one who let her get to the point where she was even entertaining Daniel. They BOTH had a part to play in the demise of their relationship. Issa’s actions were more definitive, but Lawrence’s were more damaging.