‘Insecure’ Season 4 Spoilers: Issa Rae Explains Friendship Drama, New Love & Career Goals For Her Character

Issa Rae recently explained what went into putting several elements of HBO‘s Insecure‘s Season 4 premiere together.

The comedy returned on Sunday, April 12, after being on hiatus since September 2018. The new season opens with Rae’s character, Issa Dee, revealing that she is on the outs with her best friend Molly (Yvonne Orji). The season also shows Issa’s determination to host a block party for her Los Angeles community. She had begun working on the project in Season 3 after abruptly quitting her non-profit job, We Got Y’all.

Rae recently spoke to Variety about why she opened up with a negative aspect of her character’s storyline. She explained that her showrunner, Prentice Penny, pitched the idea after she had explained how she wanted to see a story from a nonlinear approach. As the season transpires, she explains that viewers will see what led to the friends’ fallout with several clues throughout the 10 episodes.

Rae also explained why seeing Issa and Molly’s friendship shift was important for her to portray on screen. Throughout the last three seasons, Molly, who is a successful lawyer, has been superior to Issa in terms of their career goals. Now that Issa is making positive strides towards her block party idea, however, Issa says fans will get to see how Molly deals with Issa leveling up this season.

“What happens when that dynamic changes?” Rae asked when talking about Issa and Molly’s friendship. “What role do you play in that friendship, and what happens when your friends look at you through old eyes?”


Rae continued to dish on the more upbeat elements of the season. In Season 3, Issa was dating Nathan (Kendrick Sampson) who she met while she was working as a Lyft driver. As their romance blossomed, Nathan abruptly “ghosted” Issa and didn’t return her calls or texts. One month later, Nathan returned in the Season 3 finale, leaving Issa with the decision of taking him back or moving on. Season 4 reveals that she seemingly did the latter, as she begins a friends-with-benefits relationship with TSA agent Calvin (Reggie Conquest). Calvin is a plus-size man, which Rae shared was something she felt would be interesting to explore this season. She said the romance storyline was actually developed by one of the show’s writers, who had a similar experience.

“She just described what he looked like, and we were like, ‘Oh, that’s it,”‘ Rae said.

“And thinking about it, when she mentioned that we were like, We’ve never had that representation on the show before [for Issa]. Like, duh, we should. That’s what it came down to.”


Although Issa is making strides in her career and love life, the drama between her and Molly will be a focal point this season. While fans of the besties will watch their friendship dissolve, the series’ show within a show, Looking for La’Toya, is set to have plenty of comedic relief. The parody had several guest stars, including Ray J, SZA and Real Housewives of Atlanta stars Kandi Burruss and Porsha Williams.

Insecure airs on HBO at 10:00 p.m. EST.

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