Do we ever really arrive in life?
Deep down, we’re all wondering if next week, or next month or even next year will be when we finally, and irrevocably, get all our collective shit together, allowing us to relax, coast and enjoy the fruits of our hard work.
But as Issa Dee (Issa Rae) demonstrates beautifully in the fifth and final season of Insecure, it might be that we never really arrive anywhere, and that a whole a concrete, defined destination (besides, the obvious of course which no one wants, thanks very much) will always prove elusive.
It’s not an easy thing to grapple with, and Issa, her best friend Molly carter (Yvonne Orji) and the other two members of their inner circle, Kelli Prenny (Natasha Rothwell) and Tiffany DuBois (Amanda Seales) all spend much of season five trying to figure out if they are there yet, and if not, if they will ever get there.
They won’t, of course, but then no one ever really does, do they?
Insecure, a brilliantly immersive look at the lives of four up-and-coming successful Black women in Los Angeles, and those who orbit them, closely or tangentially, is well aware that life really offers any firm and solid answers to anything.
In a season which is far more concerned with where life is heading than with any great, resounding narrative punctuation points – this is a season for exploring and wrapping up, not for great twists and turns, though there are some emotionally searing moments – each of the main cast members, and of course Issa whose story has been the beating heart of Insecure since its beginning on HBO in September 2016, has to decide for themselves what it is they want from life and what really matters to them.
Issa, as noted, is the main game in town when it comes to existential crises.
In the ten, roughly 27-minute episodes (the final is little longer to allow for proper goodbyes) that makes up the season, Issa has to variously decide whether she and Molly can stay besties, which man really owns her heart, and crucially, which way she wants to take her burgeoning events career, with the company, The Blocc, really starting to gain some traction.
It’s at this point that Issa has to ask herself what success and happiness will really look like?
It might seem like an easy question on the surface, but as Issa grapples with what it might resemble, and if she’s okay with the shape it eventually if impermanently takes, she realises, so many before her, that there’s likely no one point when you can say “THIS IS IT”.
Life is never that obvious and tidy, and while some of the hallmarks of success like a bigger apartment or the money to go to nice restaurants make their presence known with every aspirational flight of fantasy – in episode eight “Choices, Okay?!” where Issa pictures where a Sliding Doors moment for her professionally might take her – the truth is, we usually don’t know what success will look like until we find it … and sometimes not even then.
In a season replete with some truly evocative musical choices, and parties and get-togethers lush with the promise of modern middle class Black life, Insecure is always asking itself, via Issa, whether we will ever know what satisfies us?
Perhaps we won’t but Issa, who is prone to overthinking things to an epic degree, and who needs to take the advice of her friends and just go with the flow, tries really hard to will it into shape all while telling herself, and yes, the extent of her self-sabotage does become obvious to her as the seasons winds to a close, that she may never make it.
Season five of Insecure, which continues a welcome and burgeoning trend in US television to reflect the gloriously rich diversity of our world as it actually is, also spends much of its thoughtfully nuanced and luxuriously unhurried storytelling – the writers manage to pack a lot into less-than-half-hour episodes, a testament to the calibre of their resonant creativity – letting its characters build on their found 9and biological) families, recognising that success means little if there aren’t significant people with which to share it.
Over the course of the ten episodes we see Molly let go of her incessant internal criticism and need for precise order in the world in favour of surrendering herself to what comes naturally, Kelli, who has ostensibly be all confidant and brassy self-togetherness own her vulnerability and need to belong, and Tiffany come to grips with a pretty big change in her own life with husband Derek, (Wade Allain-Marcus).
In the centre of it all is Issa, forging her long-wished for career promoting the richness of Inglewood, the largely Black neighbourhood in which she lives, and trying to work out who it is she wants to be with – long-time on-again, off-again beau Martin (Jay Ellis) or the luminously blue-eyed though emotionally uncertain Nathan (Kendrick Sampson), both of whom bear promise but who may or may not be the one that Issa needs in the long-term.
What ultimately defines Issa, and makes her so rewarding and accessible to watch, is her brutal honesty, fallible humanity and sense of uncertainty about where to take her life.
While her life does gain longed-for traction, it all takes place again a backdrop familiar to many of us where the linear piling up of good times, happiness and achievement does always happen we want and we are forced to handle as many steps backward as we are taking forward.
As a final season, it will not surprise anyone that Insecure‘s fifth suite of episodes does celebrate all kinds of milestones and big moments, and that it wraps up most things with a pleasing big red bow, but even in the final scene, which ends with the welcome that life will go on for Issa and Molly, and indeed all their friends and family, it sticks to its central message that we will find happiness and success, but that it may not always make itself obvious or certain and that that’s okay as we long we keep moving onward, ever onward, confident that life will take us somewhere, and that it will be sustainingly good.