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Lots happened during the season five (Byeve) premiere of “Insecure” including a Stanford University reunion, a character’s “death” and an almost inevitable split.

During the episode, Kelly is surprised to learn that she’s mistakenly made the “in memoriam” page at their alma mater. She’s even more surprised to see that Issa left a comment about her “death.”

“Am I a joke to you?” Kelly later wonders.

Also in the episode, Issa and Molly run into an old girlfriend, Cheyenne, who was previously part of their college rap group. Cheyenne is doing well for herself after dancing on tour with Ciara, and the ladies agree to all get together for a nostalgic party.

On the way to the party the ladies decide to stop by a liquor store to buy booze to pregame but on the way out they’re robbed by a man armed with a gun. Cheyenne is SHOOK and wails in fear, leading the robber to chastise her and mistakenly call her by her name.

Yes, Cheyenne was in the robbery the whole time, and after the jig’s up, she orders the ladies to give up their property. Not Issa’s shoes though because Cheyenne shadily says she doesn’t want them.


The ludicrousness of the robbery causes Issa and Molly to burst into laughter and brings them a step closer to reconciliation.

The next day after the robbery foolishness and while leaving Stacks Cafe, Issa and Molly have a conversation about Molly possibly rekindling a flame with her college hookup buddy Omari. Omari’s recently divorced and based on some not-so-subtle hints, he’s interested in pursuing Molly.

Molly goes to Issa for advice and Issa notes that she was never “pressed” about Omari.

“That’s when I thought I had all the time in the world,” says Molly. Issa remarks that maybe “they do” which apparently makes her have a revelation; it’s time to let bygones be bygones. 


“I just wanna move forward,” says Issa.

“I wanna move forward too,” agrees Molly.


Later Lawrence finally appears and he and Issa are seemingly just fine despite him expecting a baby with Condolences. Lawrence picks up Issa from the airport and they share a kiss.

On the ride home however Issa’s stewing in silence and apparently coming to terms with the inevitable.

“Lawrence I had to a chance to think and…” starts Issa before she emotionally hangs her head.

“Yeah, I know,” replies Lawrence while on the verge of tears.

And that’s it. The on-again-off-again couple is off, possibly for good.

HuffPost’s Black Voices notes that In a roundtable conversation ahead of the premiere, Issa discussed why it was important for the writers to end that chapter and noted that Issa and Molly’s relationship is the central focus of the show.

Sorry Lawrence!

“That was the most important thing for us to acknowledge and repair. That’s why the Issa and Lawrence decision happens at the end of the episode because Issa needed to figure out where she was with Molly and get that relationship repaired and using that as a foundation to kind of give her the clear head to make a decision about what was best for her,” Rae told HuffPost.


Did YOU watch the Insecure season 5 premiere?


Source: Raymond Liu / HBO

Take a look inside the episode with the Wine Down” with Issa Rae, Prentice Penny and Melina Matsoukas.


Insecure airs Sundays at 10 p.m. ET/PT on HBO. Want to watch more? The entire series is now streaming on HBO Max.


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