The skyline of New York City, a constant backdrop to dreams and dramas, has always promised a particular kind of allure. For decades, television has invited us into the lives of women navigating ambition, friendship, and the relentless pursuit of love. But the way these women are portrayed, the messy realities they’re allowed to embody, has subtly, profoundly, shifted. Today, my thoughts turn to this fascinating transformation: From Sex and the City to Fleabag: The Evolution of the Messy Woman on TV.
This isn’t just about fashion or dating; it’s about the ever-expanding space for female characters to be authentically, gloriously, and sometimes painfully, flawed. It’s about letting women on screen shed the burden of perfection and embrace the beautiful chaos of real life. And honestly, it’s a journey I, and many others, have welcomed with open arms.
Where It Began: Manolos, Martini Glasses, and Manhattan Muses
For Matthew, my amazing partner, who, bless his heart, watches with an appreciation I can only describe as profound, Sex and the City is his absolute favorite show. And you know what? He’s not wrong. When it premiered in 1998, Sex and the City was revolutionary. It showed four independent women in their thirties and forties, living in New York, openly discussing sex, careers, and friendship in a way that felt fresh, bold, and entirely new for mainstream television.
- The Pursuit of Love (and Shoes): Carrie, Charlotte, Miranda, and Samantha were iconic. They chased careers, faced dating dilemmas, and supported each other through thick and thin, all while navigating the complexities of modern womanhood. It was witty, glamorous, and often genuinely insightful.
- Open Conversations: The show dared to discuss female sexuality, orgasms, and relationship dynamics with a frankness that broke taboos. It gave women a voice in conversations that were often relegated to hushed whispers.
- Flaws, But Polished: While these women certainly had flaws (Carrie’s self-absorption, Samantha’s often-casual cruelty, Charlotte’s naivete, Miranda’s cynicism), their messes were often presented through a polished, aspirational lens. Their apartments were fabulous, their wardrobes designer, and even their emotional breakdowns looked chic. Their problems, while real, usually found a neat resolution by the end of the episode. The mess was there, but it was often accessorized.
Sex and the City gave us a glimpse of women breaking free, but still within a certain framework of aspirational perfection. The idea of the “messy woman” was hinted at, but kept largely within the bounds of a designer handbag.
The Gritty Unveiling: When the Mess Got Real (and Profound)
As television evolved, so did its willingness to explore deeper, less filtered, aspects of female experience. The conversation shifted, the lens zoomed in, and the mess became gloriously, heartbreakingly, raw.
- Girls (2012): The Messy Millennial Manifesto. Lena Dunham’s Girls unapologetically threw the polished perfection of Sex and the City out the window. It focused on the messy, self-absorbed, often unlikeable, yet profoundly relatable lives of four young women in Brooklyn navigating post-college uncertainty, bad jobs, and even worse relationships. The humor was often derived from their awkwardness, their poor choices, and their profound immaturity. It was real, unfiltered, and deeply uncomfortable at times, reflecting the genuine struggles of a generation trying to find its footing. It traded Manolos for sweatpants, and polished dating for disastrous encounters.
- Broad City (2014-2019): The Joyful Chaos of Friendship. Ilana Glazer and Abbi Jacobson’s Broad City embraced the chaos and celebrated the unapologetic friendship of two aimless, hilarious women just trying to survive (and thrive) in New York City. Their messiness was less about angst and more about wild, anarchic energy. They were broke, often high, and always, always there for each other. Their humor came from their fearless embrace of their own imperfections and their joyous refusal to conform. It showed that true female friendship could be wonderfully unpolished and fiercely loyal.
- Fleabag(2016-2019): The Holy Grail of Honest Mess. And then there is Fleabag. Written by and starring Phoebe Waller-Bridge, this show redefined the “messy woman” with a level of brutal honesty, dark humor, and raw vulnerability that was groundbreaking. Fleabag, the unnamed protagonist, is witty, sexually adventurous, often self-destructive, and perpetually grappling with grief, guilt, and a profound sense of loneliness. She talks directly to the camera, pulling the audience into her chaotic internal world.
- Unflinching Honesty: Fleabag doesn’t shy away from the ugliest, most uncomfortable aspects of female experience: self-sabotage, addiction, complicated family dynamics, bad sex, and deep, unexpressed grief. It shows the internal monologue of a woman who is witty on the surface but screaming inside.
- Vulnerability as Power: Waller-Bridge makes Fleabag’s vulnerability her greatest strength. We see her flaws, her mistakes, her desperate longing for connection, and it makes her profoundly relatable and deeply human. She is not just messy; she is broken, imperfect, and utterly captivating precisely because of it.
- Redefining “Likability”: Fleabag shattered the notion that female characters must be “likable.” Fleabag often makes terrible choices, but her honesty about those choices, and her genuine pain, makes her utterly compelling. She showed that flawed women are infinitely more interesting than perfect ones.
- Beyond the “Strong Woman”: This show moves beyond the sometimes one-dimensional “strong female character” trope. Fleabag is strong, yes, but also weak, flawed, vulnerable, and profoundly human. Her strength comes from her resilience and her ability to keep going, even when life is a painful mess.
The Evolution: From Aspiring to Authentically Flawed
The journey from Sex and the City to Fleabag marks a significant evolution in how television portrays women. It’s a move from aspirational glamour (where even flaws are carefully styled) to a raw, unvarnished honesty that embraces the discomfort, the ugliness, and the profound beauty of human imperfection.
- Sex and the City allowed women to talk about sex and careers.
- Girls allowed women to be self-absorbed and aimless.
- Broad City allowed women to be joyfully chaotic and unconcerned with societal expectations.
- Fleabag allowed women to be profoundly grieving, sexually complicated, self-destructive, and still, somehow, worthy of love and understanding.
This evolution is vital. It expands the narratives available to female characters, creating more diverse and relatable reflections for audiences. It pushes the boundaries of what is considered “acceptable” or “likable” on screen, proving that truth, in all its messy glory, is often the most compelling story of all. And in a world that often demands a polished performance, seeing women on screen embrace their authentic, imperfect selves is a profound, liberating act.