Everything We Know About 'Insecure' Season 5

The Issa Rae comedy is coming back for one final season.

Merie W. Wallace/HBO
Merie W. Wallace/HBO
Merie W. Wallace/HBO

It was just back in 2016 that Issa Rae took her talents over to HBO to adapt her popular web series Awkward Black Girl into Insecure. Now, after four successful seasons and 11 Emmy nominations, the comedy has become a mainstay and the hype around it only (rightfully) continues to grow. Following a young Black woman in LA named Issa Dee and her (mis)adventures in professional success, friendship, and love, the series co-created by Rae and Larry Wilmore has been hailed for its relatability and earnest laughs-and has drawn seriously divided lines between fans about their eye candy of choice. 

While Season 4 saw Issa and her BFF Molly (Yvonne Orji) trying to “level-up” in their personal lives, it seems like the two still have a long way to go on their own, and as a duo. Considering the season finale seemingly left many things unsaid and dropped a handful of bombshells, it’s definitely fair to start looking toward the next installment to see how everything gets patched up. While we’ll have to kill time with some mirror raps of our own as we wait for more of Issa’s, here’s everything we know about Season 5 of Insecure so far. 

Will there be a Season 5 of Insecure

Insecure is definitely coming back for a fifth season. The renewal was confirmed before Season 4 was even over, back in May 2020, as reported by Deadline. They shared that showrunners “Issa Rae, Prentice [Penny], and the whole Insecure team will be getting back together,” so it should be another round of laughs and tears as usual. 

A bit of freaking out is in order, though: Season 5 will be the final season of Insecure. Variety reported in January 2021 that the show was coming to an end. It doesn’t sound like the series was canceled, but rather the showrunners decided it was time to wrap things up appropriately, as executive vice president of HBO Programming Amy Gravitt told Variety “this talented team has conceived a brilliant final season.” At least we’ll be getting to say our goodbyes to Issa, Molly, and co., and it won’t be long till we next the next comedy project from Rae: HBO announced that she’ll be starring in and writing a new eight-episode, half-hour series called Rap Sh*t, about two erstwhile high school friends teaming up to form a rap group in Miami. Syreeta Singleton, who has written for InsecureCentral Park, and Black Monday, will be the showrunner.

When will Insecure Season 5 premiere? 

According to Popsugar, filming on Season 5 was well underway in February 2021. As the comedy isn’t much of a heavy production lift, it seems likely that shooting should wrap up this winter/early spring and then move into post-production shortly after. It’s confirmed that the upcoming, final episodes will hit HBO sometime this year, so we’d place our bets on seeing new episodes sometime this summer/early fall.

Who in the cast is returning?

Insecure wouldn’t be the same without its core cast, so you can assume that all of the main leads will be back. Issa Rae will reprise her role as Issa Dee, Yvonne Orji will be back as Molly, as well as Natasha Rothwell as Kelli, Jay Ellis as Lawrence, and Amanda Seales as Tiffany. 

Now that Andrew (Alexander Hodge) and Molly broke up, though, it’s hard to say if we’ll be seeing any more of Asian bae. But as for Condola (Christina Elmore), it seems like she’ll definitely be sticking around, given the news she dropped in the season finale. More on that reveal below, but when you consider the detour that throws in Issa’s relationship with Lawrence, it might be time for Nathan (Kendrick Sampson) hive to shine and for that ex to be back in the picture as well. At the very least, photos caught the actor on set in a scene alongside Issa, so it’s certain he’ll appear at least a bit. 

Merie W. Wallace/HBO
Merie W. Wallace/HBO
Merie W. Wallace/HBO

What will Season 5 be about? 

According to showrunner Prentice Penny, the final season hinges on one question: “If life doesn’t look like how you imagined it, does that mean it’s a success or a failure?” He spoke to Entertainment Weekly about what that means and how it should carry into Season 5, and it builds upon just about every one of the developments from that jaw-dropping finale. 

While Issa and Molly attempted to talk things out after their relationship took a hit when they each tried to focus on their own lives, their friendship isn’t necessarily going to be back to normal. Penny said, “We don’t want them to go back to where they were. They’re going to be forever changed by this, forever humbled by this, and hopefully, forever close by this.” He explained that the new episodes will explore what the road back to their close friendship, and ultimately the “2.0 version” of it, will look like. 

Where their relationship stands isn’t the only unpredictable wrench thrown into Issa’s life that’ll be explored going forward. Penny explained to EW that it was intentionally left uncertain whether or not Issa and Lawrence are still an item, but now that Condola is pregnant with his child, Issa will have to reevaluate whether or not she still wants a life with him even if it’s not the ideal one she imagined. Could that send her back onto the Nathan train? It’s hard to say, but it’ll certainly affect Lawrence individually, and whatever relationship remains between the two of them. 

On top of dealing with all that drama, Rae told Popsugar that what she’s really hoping for next season is for her character to start feeling “comfortable.” She said, “I don’t think we’ve ever seen her be that … We’ve always talked about this show as being a journey to get these characters to a place where they’re secure with their insecurities, and so that’s what I want for her, whether that’s through her man, through her passion. Whatever it is, I just want her to find her footing and be okay-and also not broke.” It’s what we want for her, too.

Continue to check back, as we’ll continue to update this post as more information regarding what’s up with our favorite L.A. friends is announced.Need help finding something to watch? Sign up here for our weekly Streamail newsletter to get streaming recommendations delivered straight to your inbox.

Sadie Bell is the entertainment editorial assistant at Thrillist. She’s on Twitter at @mssadiebell.


Where to Celebrate Lunar New Year 2023 in Australia

And what it means to be in the year of the Rabbit.

where to celebrate lunar new year australia

Starting with the new moon on Sunday, January 22, this Lunar New Year ushers in the year of the Rabbit. We’ve put together a guide on celebrating the Lunar New Year in Australia.

What is special about the year of the Rabbit?

As you might know, each year has an animal sign in the Chinese Zodiac, which is based on the moon and has a 12-year cycle. This year, we celebrate the year of the rabbit, known to be the luckiest out of all twelve animals. It symbolises mercy, elegance, and beauty.

What celebrations are taking place and how can I get involved?

There are plenty of festivals happening all around the country which you can get involved with. Here they are per state.

New South Wales

Darling Harbour Fireworks
When: Every year, Sydney puts on a fireworks show, and this year, you can catch it on January 28 and February 4 at 9 pm in Darling Harbour.

Dragon Boat Races
When: Witness three days of dragon boat races and entertainment on Cockle Bay to usher in the Lunar New Year. The races will commence on January 27 and finish on January 29.

Lion Dances
When: Catch a traditional Lion Dance moving to the beat of a vigorous drum bringing good luck and fortune for the Lunar New Year. The dance performances will happen across Darling Harbour on Saturday, January 21, Sunday, January 22, and Sunday, February 4 and 5, around 6 pm and 9 pm.

Lunar New Year at Cirrus Dining
When: Barangaroo’s waterfront seafood restaurant, Cirrus, is celebrating the Year of the Rabbit with a special feast menu. Cirrus’ LNY menu is $128pp with optional wine pairing and is available from Saturday, January 21, to Sunday, February 5.

Auntie Philter
When: Hello Auntie’s owner and executive chef, Cuong Nguyen will be dishing out some of the most classic Vietnamese street foods with his mum, Linda. All of Philter’s favourites will be on offer, as well as Raspberry Pash Beer Slushies and other cocktails being served at the Philter Brewing rooftop bar on Sunday, January 22 and Sunday, January 29.


Lunar New Year Festival
When: Ring in the Lunar New Year with food, music, arts, and more on Sunday, January 22, from 10 am to 9 pm.

Lunar New Year at the National Gallery of Victoria
When: Celebrate the year of the rabbit at the National Gallery of Victoria’s festival of art, food, and art-making activities for everyone from 10 am-5 pm.


BriAsia Festival
When: From February 1-19, Brisbane will come alive with performances, including lion dances and martial arts displays. There will be street food, workshops, comedy and more.

South Australia

Chinatown Adelaide Street Party
When: Adelaide is set to hose a fun-filled day celebrating the Chinese New Year on Saturday, January 28, from 12 pm to 9 pm.

Western Australia

Crown Perth
When: Across January and February, Crown Perth hosts free live entertainment, including colourful lion dances, roving mascots, and drumming performances. The restaurants will also throw banquets and menus dedicated to the Lunar New Year.

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