The Best ‘Sad Girl in Her Twenties’ Novels to Read and Weep

Published on 6/27/2023

Recently, I was looking at the reviews for a book I had just read, and I saw it described as a “sad girl in her twenties book”. They were right, it really was one. Finally, I had a name for all these books I had been reading and loving for years.

‘Sad girl in her twenties’ is my favourite genre, and I’d been lacking the term to describe it.

There is something so satisfying about these slow books that are usually character-driven rather than plot-driven. They all differ, but time and time again, you get the self-sabotaging main character, the concerned yet offended best friend, the bad news love interest (who is usually older), and the ambition to be some kind of artist.

I absolutely adore this genre, even though I usually don’t like any of the characters.

So if you’re ready to explore more books about sad girls in their twenties, here are the seven that I’d recommend starting with.

1. Careering - Daisy Buchanan

When I was buying this book in a store, the guy behind the checkout smirked and said, “Yeah, my girlfriend loved this one.”

And you know what? His girlfriend has excellent taste, then.

This book was more plot-driven than ‘sad girl in her twenties’ novels usually are. The main character had more of a drive to her, an ambitious greed that I could really relate to.

While a lot of the novels in this genre approach sex, this one explored how we discuss sex as well. Given the popularity of sex writers nowadays, it was fascinating to see how they can be fetishised by their own staff, to the extent that their consent is almost removed. You see Imogen grow more and more uncomfortable, and almost begin to resent her sexuality.

“Imogen has always dreamed of writing for a magazine. Infinite internships later, Imogen dreams of any job. Writing her blog around double shifts at the pub is neither fulfilling her creatively nor paying the bills.

Harri might just be Imogen's fairy godmother. She's moving from the glossy pages of Panache magazine to launch a fierce feminist site, The Know. And she thinks Imogen's most outrageous sexual content will help generate the clicks she needs.

But neither woman is aware of the crucial thing they have in common. Harri, at the other end of her career, has also been bitten and betrayed by the industry she has given herself to. Will she wake up to the way she's being exploited before her protégé realises that not everything is copy? Can either woman reconcile their love for work with the fact that work will never love them back? Or is a chaotic rebellion calling…” - Careering, Daisy Buchanan

2. Milk Fed - Melissa Broder

I’ll be honest: I haven’t recommended this book to many of my friends.

That’s not to say that it wasn’t good. This book was absolutely incredible. To say I devoured it would be a cliche, but an accurate one. It was one of the best books I read in 2022.

I feel a little embarrassed recommending it as it is rather graphic. It has some very explicit sex scenes, that border on disgusting. But that’s also what made the book so good. It blurred the lines between fetish and hunger.

It was a book all about hunger. The hunger for food, sex, love and belonging. The main character has an eating disorder, and I appreciate how graphically and bluntly it is described. It could definitely be triggering for some, but as someone whose been recovered for a few years, I found it really refreshing and non-glorifying.

“Rachel is 24, a lapsed Jew who has made calorie restriction her religion. By day, she maintains an illusion of existential control through obsessive food rituals while working as an underling at a Los Angeles talent management agency. At night, she pedals to nowhere on the elliptical machine. Rachel is content to carry on subsisting - until her therapist encourages her to take a 90-day communication detox from her mother, who raised her in the tradition of calorie counting.

Rachel soon meets Miriam, a zaftig young Orthodox Jewish woman who works at her favorite frozen yogurt shop and is intent upon feeding her. Rachel is suddenly and powerfully entranced by Miriam - by her sundaes and her body, her faith and her family - and as the two grow closer, Rachel embarks on a journey marked by mirrors, mysticism, mothers, milk, and honey.” - Milk Fed, Melissa Broder

3. Beautiful World, Where Are You? - Sally Rooney

I won’t claim that this is Sally Rooney’s best novel or that everyone will love it. I don’t know a single novel that everyone would love, and if I did, it would be a terrible book to appeal to everyone.

I will say that this book encaptures the ‘sad girl in her twenties’ trope so well. In particular, it covers the aspect of co-dependent friendships in your twenties. I think many of us have had a friendship that we now realise was too much, one where your ego was so wrapped up in them and the success of the relationship. The highlight of this novel were scenes of Alice and Eileen together, even though they could be infuriating.

Sally is excellent at creating flawed characters that don’t fall into the typical ‘unlikeable character’ trope. Many are frustrated by how passive they can be, but I find that to be a testament to how realistic they are. I think we’re all prone to forget how passive we are in our own lives, and how often the ‘miscommunication trope’ is choosing our decisions for us. Check out my list of books you’ll like if you enjoy Sally Rooney.

“Alice, a novelist, meets Felix, who works in a warehouse, and asks him if he’d like to travel to Rome with her. In Dublin, her best friend, Eileen, is getting over a breakup, and slips back into flirting with Simon, a man she has known since childhood.

Alice, Felix, Eileen, and Simon are still young―but life is catching up with them. They desire each other, they delude each other, they get together, they break apart. They have sex, they worry about sex, they worry about their friendships and the world they live in. Are they standing in the last lighted room before the darkness, bearing witness to something? Will they find a way to believe in a beautiful world?” - Beautiful World, Where Are You? Sally Rooney

4. Sweetbitter - Stephanie Danler

This novel differs from the others on the list through the glitz and glamour dripping from it. Set in the New York restaurant industry, it is fast, witty and raw. I loved the glimpse into food writing and culinary explorations. Especially as I was often reading this while eating my sad bowl of oatmeal.

It’s a novel of self-discovery, and how that can often occur when discovering something else, in this case New York and the restaurant business. It’s gritty and almost difficult to read at times, but that’s what made it so good.

“Newly arrived in New York City, twenty-two-year-old Tess lands a job working front of house at a celebrated downtown restaurant. What follows is her education: in champagne and cocaine, love and lust, dive bars and fine dining rooms, as she learns to navigate the chaotic, enchanting, punishing life she has chosen.

The story of a young woman’s coming-of-age, set against the glitzy, grimy backdrop of New York’s most elite restaurants, in Sweetbitter Stephanie Danler deftly conjures the nonstop and high-adrenaline world of the food industry and evokes the infinite possibilities, the unbearable beauty, and the fragility and brutality of being young and adrift.” - Sweetbitter, Stephanie Danler

5. A Very Nice Girl - Imogen Crimp

This was the book that I saw described as “sad girl in her twenties”, and that captures it perfectly.

There is such a loneliness to this novel. It is both detached and vulnerable. It is honest and yet guarded. Imogen managed to capture the character perfectly. And while you wouldn’t necessarily relate to Anna yourself, you can definitely imagine being her friend and wanting to give her a massive shake and reality check.

It captures the self-sabotaging element that seems to define this genre. You keep reading just to see what they’ll do next. As even though the character infuriates you, to an obsessive extent, you need to know that things will turn out alright for them in the end.

“Anna doesn’t fit in. Not with her wealthy classmates at the selective London Conservatory where she unexpectedly wins a place after university, not with the family she left behind, and definitely not with Max, a man she meets in the bar where she sings for cash. He’s everything she’s not―rich, tailored to precision, impossible to read―and before long Anna is hooked, desperate to hold his attention, and determined to ignore the warning signs that this might be a toxic relationship.

As Anna shuttles from grueling rehearsals to brutal auditions, she finds herself torn between two conflicting desires: the drive to nurture her fledgling singing career, which requires her undivided attention, and the longing for human connection. When the stakes increase, and the roles she’s playing―both on stage and off―begin to feel all-consuming, Anna must reckon with the fact that, in carefully performing what’s expected of her as a woman, she risks losing sight of herself completely.” - A Very Nice Girl by Imogen Crimp

6. Insatiable - Daisy Buchanan

One look at the cover of this novel will tell you a lot of what you need to know. I mean it; click on the link and take a look.

This is a naughty book. I say that in a gleeful tone, not a disparaging one.

This novel centres on lust. Not just the lust for sex, although there is plenty of that, but the lust to succeed, to be someone, to be wanted by someone. It’s a desire to be loved, especially by yourself.

I included two books by Daisy on this list, and if I’d read more of her work, I probably would’ve included those as well! Daisy has a brilliant way of stripping things down to their simplest form while also writing prose that could be poetic in any other light. She excels at writing books about women in their twenties.

“Stuck in a dead-end job, broken-hearted, broke and estranged from her best friend: Violet's life is nothing like she thought it would be. She wants more - better friends, better sex, a better job - and she wants it now.

So, when Lottie - who looks like the woman Violet wants to be when she grows up - offers Violet the chance to join her exciting start-up, she bites. Only it soon becomes clear that Lottie and her husband Simon are not only inviting Violet into their company, they are also inviting her into their lives.

Seduced by their townhouse, their expensive candles and their Friday-night sex parties, Violet cannot tear herself away from Lottie, Simon or their friends. But is this really the more Violet yearns for? Will it grant her the satisfaction she is so desperately seeking?” - Insatiable, Daisy Buchanan

7. My Year of Rest and Relaxation - Ottessa Moshfegh

This is a book that requires little introduction. But just in case you haven’t seen it absolutely everywhere, as I have, I’ll mention why it earned a spot on this list.

I have dreamed of just never leaving my bed. Not in the ‘Oh, I want to sleep five more minutes’ way, but more of a ‘My depression is literally too exhausting and never going away’. So when I saw the concept of this novel, my curiosity was immediately snatched up.

This book captures depression in its lethargy, monotony and egoistic thinking. It’s one of the strangest books I’ve read but was so compelling in its oddity.

It’s a slow and thoughtful novel that captures many of the self-indulgent thoughts that define our twenties.

“Our narrator should be happy, shouldn't she? She's young, thin, pretty, a recent Columbia graduate, works an easy job at a hip art gallery, lives in an apartment on the Upper East Side of Manhattan paid for, like the rest of her needs, by her inheritance. But there is a dark and vacuous hole in her heart, and it isn't just the loss of her parents, or the way her Wall Street boyfriend treats her, or her sadomasochistic relationship with her best friend, Reva. It's the year 2000 in a city aglitter with wealth and possibility; what could be so terribly wrong?

My Year of Rest and Relaxation is a powerful answer to that question. Through the story of a year spent under the influence of a truly mad combination of drugs designed to heal our heroine from her alienation from this world, Moshfegh shows us how reasonable, even necessary, alienation can be. Both tender and blackly funny, merciless and compassionate, it is a showcase for the gifts of one of our major writers working at the height of her powers.” - My Year of Rest and Relaxation, Ottessa Moshfegh

Books about sad women in their twenties are like catnip to me. As much as I love a fast-paced fantasy novel, or a heartwarming romance, there is just something so raw about the misery of youth.

These characters are often so unlikeable, mainly because they act like a mirror to us. It’s hard to see your darkest thoughts splayed out on a page and not resent a character for having the audacity to think as you do. These books often feel like a big game of ‘what if?’ to me.

What if I just ruined my life? What if I slept with that person who will only hurt me? What if I’ll never really be happy?

Keep a box of tissues close and dig in to these 7 books about sad girls in their twenties.

Looking for more reading recommendations? Check out the best books I’ve read so far this year.

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Welcome to Symptoms of Living! A place where I like to relieve myself of the barrage of thoughts and ideas filling my mind. Here I'll take a look at various topics, from books to BPD, series to self-harm, there's nothing that we can't, and shouldn't, talk about.

Having struggled with mental illness since the age of 15, one of the hardest parts was how alone I felt in it. While mental illness is beginning to be discussed more openly, and featured in the media, I still think there is room for improvement. So whether it is mental illness or merely mental health, a bad day or a bad year, let's make this a place to approach it and strip it back. Everyone has their own symptoms of living, and you certainly won't be the only one with it.

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