Season 5 of Insecure started off with a bang. Insecure, the HBO sitcom about an African-American woman and her life in Los Angeles, has always been one of my favourite shows. In Season 4, Issa Rae’s character came into her own as an independent businesswoman who could not be pushed around by anyone including herself. In this season she is still strong but less sure of herself due to some major changes in her life. Know everything about Insecure Season 5.
Release date of Insecure Season 5:
24th October 2021
Cast and characters:
-Yvonne Orji as Molly: Insecure season five is all about the changes in Molly’s life. In Season Four, she was an extremely successful lawyer who fought for equality and to is respected by her colleagues at work. In this season, however, she has lost some of that drive which has led to problems in both love and career.
-Jay Ellis as Lawrence: In-secure is Lawrence’s story. In season four he was still working at the law firm but has now left that behind him to pursue his dream of being an entrepreneur, having founded a business that makes T-shirts designed by local artists.
-Issa Rae as Issa: In insecure series five sees Issa continue on her journey towards owning herself and being comfortable with her own skin. In this season, Issa is now working at a non-profit and we see how she deals with the struggles of getting what you want in life – be that career success or finding love – which has always been something that Insecure fans have related to and resonated with.
-Yvonne Orji as Molly: Insecure series five sees Molly take on the next chapter in her life, she is now working at a non-profit and we see how she deals with the struggles of getting what you want in life – be that career success or finding love – which has always been something that Insecure fans have related to and resonated with.
-Natasha Rothwell as Kelli: Insecure series five sees Kelli continue to find her footing and in Insecure Season Five we see her re-evaluate what she wants in life.
-Amanda Seales plays Tiffany: Insecure series five sees Tiffany moving on from Insecure Season Four’s finale, where she decided to leave her cheating boyfriend Dro. In Insecure Series Five, we see how the aftermath of that decision affects not only herself but also those around her too.
-Lisa Joyce as Frieda: Insecure series five will bring back Lisa Joyce in the role of Frieda. In Insecure Season Five, we see her re-enter the lives of Issa and Molly as she takes over ‘The Spot’ after it has been taken away from Lawrence (Jay Ellis).
Plot details of Insecure Season 5:
In Insecure Season Five, Issa Rae is facing a new dynamic at work with her promotion. She has to navigate complicated relationships and difficult situations in order to continue growing as she starts pursuing her dreams of becoming one of the most innovative minds in social media.
Issa’s friends are supportive but not fully understanding after they’ve failed her when it counts. In Insecure Season Five, Molly is in a good place with Dro and she has the opportunity to really get what she’s always wanted.

Synopsis:
In Insecure Season Five, Issa is having trouble figuring out what she wants to do with her professional life. At the same time, Issa struggles in her relationships and ends up jeopardizing one of them.
Molly’s friends are concerned about their own lives after Molly begins acting erratically when she gets together with Dro for a night on the town. In Insecure Season Five, Tasha is trying to figure out what she wants to do with her life while Kelli begins questioning hers after some shocking news comes their way.
#InsecureHBO coming to an end definitely has us in our feelings 😭 https://t.co/QEfZ76Tjaw
— Shadow and Act (@shadowandact) September 29, 2021
Insecure series five sees Molly take on the next chapter in her life, she is now working at a non-profit and we see how she deals with the struggles of getting what you want in life – be that career success or finding love – which has always been something that Insecure fans have related to and resonated with.
What’s new in season five?
In Insecure Season Five, Molly is happy to enjoy being single and also has a new love interest in the form of an investment banker called David (played by Jay Ellis). In Insecure Season Five, we see how Issa’s life begins to go into freefall after she agrees to help Daniel with his campaign – which then creates all kinds of problems in her relationship with Molly. We get to see Issa trying out rapper-dating after she decides that Lawrence isn’t good enough for her anymore and the consequences of this decision are hilarious if a little too close to home at times!
In season Five, Khloe Kardashian is back in action as Tiffany DuBois and, like in Insecure Season Four, she provides the most laughs of any character with her combination of ignorance and entitlement.
In Insecure Season Five, we see Issa Dee return to work after quitting at the end of Insecure Season Three but then having to come back because that’s not how life works!