Everything We Know About 'Insecure' Season 4

Adapted from her career-catapulting web series Awkward Black Girl, Issa Rae's HBO series Insecure has become one of TV's best series. It's been praised for its diverse team of writers and ability to tell nuanced stories about a pair of 20-something best friends in LA, navigating love, their careers, and the black American experience. Rae, showruns the series she stars in, has gotten her fair share of awards recognition with two Golden Globe nominations and one Emmy nom for her performance as the relatable Issa Dee. 

There's been a lot to both laugh and cry about over three seasons as Issa and Yvonne Orji's Molly weave in and out of toxic relationships and face the conflicts of everyday life -- and the end of Season 3 set up a ton of intriguing storylines to look forward to in the show's fourth season. Old flings come out of the woodwork, new flings abound, and tensions run high among their friends. In anticipation of what's coming Issa and Molly's way, here's everything we know so far about Insecure Season 4. 

Is there going to be a Season 4 of Insecure?

Hell yeah! Back in September 2018, Issa Rae announced the HBO series would be back for a fourth season. 

While Rae once joked that she would cancel the show if she found out Melania Trump watched it -- a comment she made to Glamour in 2018 when explaining what it was like to talk to Michelle Obama about Insecure -- it is, in fact, coming back. (Whether the current First Lady will continue tuning in, as her Director of Communications claims she does, remains to be seen, but it looks like Rae couldn't care less.)

When will Insecure Season 4 premiere? 

After what felt like an eternity, HBO finally announced Insecure Season 4 is scheduled to premiere on Sunday, April 12. Back in April 2019, HBO programming chief Casey Bloys explained to Vulture that the show wasn't following its typical yearly release schedule (Season 1 debuted in October 2016, 2 in July 2017, and 3 in August 2018) for the upcoming season because "Issa became a big movie star," with lead roles in films like The Photograph (opposite Lakeith Stanfield) and the forthcoming The Lovebirds (opposite Kumail Nanjiani). While you may have to wait a little longer than usual, don't worry too much: Bloys stressed that the star "partly wanted a break to come back to [Insecure] fresh," so it should be better than ever. 

Is there a trailer for Insecure Season 4?

HBO announced the premiere date with a fun teaser featuring not one, but three Issa Dees trying on a series of stylish yet professional fits, gassing herself by doing one of her classic mirror raps. The clip doesn't reveal a whole lot, but it looks Issa's got a whole new 'tude and ready to take on the world with some optimism. Other than that, it mostly just stirs up a whole lot of feelings of how much you've probably been missing this character and series.

How many episodes will there be?

Per Deadline, Issa Rae confirmed during the TCA panel for her HBO series A Black Lady Sketch Show that Season 4 will have 10 episodes. That’s a bit more than Seasons 1-3, each of which only featured eight episodes.

Who will be in the cast of Insecure Season 4? 

The show is created by and starring Issa Rae, so she'll obviously be reprising her role as Issa, and Yvonne Orji will definitely be back as her best friend, Molly. Plus, their core friend group, like Lisa Joyce (Frieda), Y’lan Noel (Daniel), Natasha Rothwell (Kelli), and Amanda Seales (Tiffany), should also be back, too. Molly’s latest love interest Andrew (AKA Asian Bae), played by Alexander Hodge, has also been moved up to a series regular, according to Deadline. Given that his character's roommate is coming back, last season's newcomer Kendrick Sampson, who plays Nathan, should be too. 

For awhile, it was up in the air whether we would be seeing the Best Buy employee you can't help but love/hate, Jay Ellis' Lawrence, again or not. When Lawrence and Issa broke up way back at the end of Season 2, it was said that he would no longer be on the show -- an absence that pissed off the #LawrenceHive so much, they started a petition for his return. Inevitably, he was back toward the end of Season 3, this time with a new boo whose identity remains unknown to Issa. She just so happens to be Condola, Issa's potential new business parter, who got increasingly more serious with Lawrence throughout the end of the season. Alas, he will be back. That means Condola will probably also be there, setting the season up for a seriously uncomfortable confrontation if Issa keeps working with Condola -- their relationships and histories might make for an interesting work/life balance. 

Who else is involved this season?

Kerry Washington revealed on Instagram in November that she would be directing episode 9 of the series' fourth season, joining a roster of guest directors that includes Watchmen star Regina King. 

What will Insecure Season 4 be about? 

Aside from the seemingly inevitable conflict between Issa and Condola, Issa and Molly's relationship could be put to the test in Season 4. Never have the two really dated men from the same circle, and they've both kept those parts of their lives relatively separate from their friendship with each other -- meaning, they're entering uncharted waters dating a pair of roommates. Molly is moving into a new relationship with Andrew (Alexander Hodge), AKA Asian Bae, and Issa seems to be picking things back up with Nathan (Kendrick Sampson). As Refinery29 pointed out, in the Season 3 finale post-show special Wine Down, executive producer Prentice Penny said fans can expect these new relationship dynamics to be a large focus of the upcoming season. He said, "Typically, we've always had their relationships as 'Issa's dating this guy' and 'Molly’s dating this guy.' And never the 'twain shall sort of meet... what’s interesting now is what will this friendship be like [in a new situation]?" Sounds like a lot of drama over boundaries to come! 

That's all while Issa continues to work on herself, according to Rae who spoke on a Television Critics Association panel in January 2020. She said now that the character quit her job, she's ready to "level up" and enter the next phase of her life professionally, as well as personally. But just as much as she's trying to thrive, Rae said that all comes with examining "the fallout that happens when turning 30."

It's also a possibility that mental health becomes more of a central focus, as it was revealed that Nathan ended up ghosting Issa not because he didn't want to see her anymore, but because he needed to go home to Houston to sort out his personal issues.

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