‘Insecure’ Recap, Episode 5: “Shady As F**k”

Spoiler alert: ISSA CHEATED ON LAWRENCE WITH DANIEL BECAUSE OF COURSE SHE DID.

I knew it was going to happen, but that doesn’t make it any less disappointing (and relatable) when Issa and Daniel have sex on episode five of Insecure, “Shady as F**k.”

It wasn’t Issa staying late at Daniel’s studio, after a recording session, that gave it away; by then, the chance of them not having sex was close to zero. It wasn’t him cleaning Issa’s shirt after she spilled her drink that gave it away, because we’ve seen that scene before.

It was Issa time and time daydreaming and fantasizing of being with him, even when she had convinced herself that he was a think of the past (“Boy, bye”) and her relationship with Lawrence seemed to have gotten smoother. (What’s funny is that she mostly daydreamed and fantasized of him, or of them, in a more sexual, intimate sense; she didn’t necessarily daydream on the life with him they could’ve or could have.)

And while I don’t believe him, at the latter end of episode five, Daniel finally implies that he too thinks of what could’ve been and has his own share of what ifs. Here’s a snippet of their conversation:

Daniel: Why you never give me a shot? Yeah, we were long distance and shit, but you never took me serious.

 Issa: We were friends with benefits because you wanted to go do your thing out in the streets. So, it’s on you.

Daniel: How is it on me?

Issa: Now you’re really gonna act like you don’t know?

 [Issa reminisces of a time where they spent the entire day going from one taco truck to the next because Daniel wanted to find a specific sauce.]

Issa: I thought you were gonna say…I don’t know…make things official. Give us a shot, but you didn’t.

Daniel: I should have. I wanted to. Maybe you’re right. Maybe I wasn’t ready then.

Issa: You should’ve said something.

Daniel: I know, I know. What if I’m ready now?

WHAT IF I’M READY NOW? How dare he?

They kiss, but she stops him because oh you know, she has a boyfriend, and he acts like he forgot. (He doesn’t care; and why should he, when she doesn’t seem to?) But then, she kisses him–maybe because she can’t have another what if, maybe because she doesn’t want any what ifs anymore, maybe because regret is a heavy burden to carry.

His what if(s) is what seal the deal, and make Issa give into hers.

Issa isn’t the only one in a crash seen from a far, but can’t be stopped…

Molly yet again gets ahead of herself, planning out a life for her and love interest, Chris (played by singer Jidenna) aloud, that he isn’t ready for. (I’ll give it to Molly, that instead of playing along, while not ill intended, he should’ve been clear as soon as he felt uncomfortable.)

After a few dates, Chris spends the night at Molly’s. The number of times he’s slept over up until this time, or whether this is his first time sleeping over, isn’t clear, but he’s not ready to leave a spare suit at her place, as Molly quickly implies. She then asks Chris to join her at her co-worker’s engagement party around two to three times, each in a different way. He first tells Molly that he’d like to play it by ear, and after the third time, he says yes.

Chris not only shows up, but plays along when asked if he’s her boyfriend. Excited, but confused, Molly asks if that’s where they’re at. Chris replies with a hard, “no,” saying he thought she “needed a win.”

“You asked me to come repeatedly. We barely even know each other and you’re talking about me leaving clothes at your spot, making plans six months advance…” Chris says, before Molly asks him to leave.

I don’t think Molly intends to seem thirsty for love; I think she gets excited at the idea of a future with someone when it’s going well; the minute she eyes potential, she puts dating on overdrive.

[Watch Insecure, Episode 5, “Shady as F**k” on HBO Now]

Erika Ramirez–born in San Jose, CA and based in Brooklyn, NY–is a freelance writer, editor, and producer. She’s the founder of digital magazine, ILY, which is about love. She’s held editorial positions and written for various outlets as Billboard, ROOKIE, NPR, Milk Studios and more. Follow her on Twitter: @3rika