The best books about middle-aged women that will make you snort laugh

Why am I passionate about this?

I’m the author of two novels, a memoir, and numerous essays and humor pieces. As a reader, I’ve always been drawn to strong, flawed, funny female characters and voices. The pull is even stronger now that I’m at midlife, a phase that’s equal parts misery, hilarity, and night sweats. I read a wide range of books, from literary fiction and classics to psychological thrillers to graphic novels that I steal from my teenagers when they’re not looking. But I have a special place in my heart for books that explore the many facets of what it means to be a woman “of a certain age” today, while making me laugh—and sometimes cringe—with recognition. 


I wrote...

Book cover of The Society of Shame

What is my book about?

Kathleen Held’s life is turned upside down when she arrives home to find her house on fire and her politician husband on the front lawn in his underwear with an attractive, half-dressed young staffer. But the scandal that emerges isn’t the affair; it's that a photo taken by an eyewitness captures a period stain on the back of Kathleen’s pants. 

When the image goes viral, Kathleen is catapulted to unwanted fame as the figurehead for a new women’s rights movement, #YesWeBleed. Hilarious and heartfelt, The Society of Shame is a satirical romp through internet activism, online shaming, and politics, as well as a tender mother-daughter tale.

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

The books I picked & why

Book cover of Mrs. Fletcher

Jane Roper Why did I love this book?

As a parent on the verge of becoming an empty nester (noooooo!!), I was immediately drawn to Mrs. Fletcher. The titular character is a 46-year-old divorcee who has a sexual awakening—and develops an appetite for online porn—after her son leaves for college. Her son, meanwhile, gets his own education in sex, gender, and consent on campus. It’s an entertaining and surprisingly sweet exploration of sexuality, relationships, and the ways people navigate turning points in life. 

By Tom Perrotta,

Why should I read it?

1 author picked Mrs. Fletcher as one of their favorite books, and they share why you should read it.

What is this book about?

New York Times bestseller!
Now a major Sky/HBO TV series

From the bestselling author of The Leftovers and Little Children comes a penetrating and hilarious new novel about sex, love, and identity on the frontlines of America's culture wars.

Eve Fletcher is trying to figure out what comes next. A forty-six-year-old divorcee whose beloved only child has just left for college, Eve is struggling to adjust to her empty nest when one night her phone lights up with a text message. Sent from an anonymous number, the mysterious sender tells Eve, "U R my MILF!" Over the months that follow,…


Book cover of I'm Wearing Tunics Now: On Growing Older, Better, and a Hell of a Lot Louder

Jane Roper Why did I love this book?

I’ve enjoyed Wendy Aaron’s humor writing for years, but even if I hadn’t, I think I would have bought this book based on the title alone. I’m Wearing Tunics Now is a hilarious memoir about the absurdities, indignities, and, yes, benefits of being a middle-aged woman. If you’re Gen-X or thereabouts, you will totally relate to the humor and references. The book includes a lot of funny lists, in the style of McSweeney’s, so it’s the kind of read you can pick up and enjoy in bite-sized pieces.

By Wendi Aarons,

Why should I read it?

1 author picked I'm Wearing Tunics Now as one of their favorite books, and they share why you should read it.

What is this book about?

An honest and hilarious memoir about second acts, self-acceptance, and celebrating what happens when a woman gets older, wiser, and a lot more excited by sales at Eileen Fisher.

A late bloomer who came to her career later in life, humorist Wendi Aarons shares the joys, stumbles, and outfit mishaps she’s experienced on her road to no longer giving a f***. It's a journey from chunky heels and bad choices from the juniors department to the panache of a comfortable linen tunic (metaphorically, but also literally), enjoying her second act and unapologetically chasing her dreams. With relatable personal anecdotes, an…


Book cover of Where'd You Go, Bernadette

Jane Roper Why did I love this book?

There’s something cathartic about reading a midlife meltdown story, and this one is over-the-top hilarious. Once a successful architect, the eccentric, misanthropic Bernadette Fox is fed up with what her life has become. When she disappears without a trace, her precocious teenage daughter sets out to track her down. The story is told almost entirely through emails, letters, memos, and other bits of correspondence, making it a fast, fun read. 

By Maria Semple,

Why should I read it?

12 authors picked Where'd You Go, Bernadette as one of their favorite books, and they share why you should read it.

What is this book about?

A misanthropic matriarch leaves her eccentric family in crisis when she mysteriously disappears in this "whip-smart and divinely funny" novel that inspired the movie starring Cate Blanchett (New York Times).

Bernadette Fox is notorious. To her Microsoft-guru husband, she's a fearlessly opinionated partner; to fellow private-school mothers in Seattle, she's a disgrace; to design mavens, she's a revolutionary architect; and to 15-year-old Bee, she is her best friend and, simply, Mom.

Then Bernadette vanishes. It all began when Bee aced her report card and claimed her promised reward: a family trip to Antarctica. But Bernadette's intensifying allergy to Seattle --…


Book cover of Impersonation

Jane Roper Why did I love this book?

I love it when stories are told through the lens of contemporary issues but still manage to be deeply personal and funny. Impersonation fits the bill, taking place against the backdrop of #MeToo and the Trump presidency, and starring sharp-witted forty-year-old single mom Allie Lang, who you root for right from the start. Allie is hired ghostwrite the memoir of a high-powered feminist with political ambitions, to make her seem more maternal and relatable. It’s a nearly impossible task—until Allie starts bringing herself to the page. 

By Heidi Pitlor,

Why should I read it?

1 author picked Impersonation as one of their favorite books, and they share why you should read it.

What is this book about?

"By turns revealing, hilarious, dishy, and razor-sharp, Impersonation lives in that rarest of sweet spots: the propulsive page-turner for people with high literary standards." --Rebecca Makkai, author of The Great Believers TOGETHER, THEY MAKE THE PERFECT FEMINIST MOTHER

Allie Lang is a professional ghostwriter and a perpetually broke single mother to a young boy. Years of navigating her own and America's cultural definition of motherhood have left her a lapsed idealist. Lana Breban is a high-profile lawyer, economist, and advocate for women's rights with designs on elected office. She also has a son. Lana and her staff have decided she…


Book cover of Wow, No Thank You.: Essays

Jane Roper Why did I love this book?

Reading Samantha Irby’s raw, hilarious, and totally uninhibited essays, you feel like you just found the funniest person at the party, and all you want to do is settle in with your drink and listen. Irby’s third essay collection finds her at forty, writing about everything from aging to friendship to bodily functions (lots of bodily functions!) with her signature self-deprecating humor, hyperbole, and cut-through-the-B.S wisdom. 

By Samantha Irby,

Why should I read it?

3 authors picked Wow, No Thank You. as one of their favorite books, and they share why you should read it.

What is this book about?

Winner of 2021 Lambda Literary Award for Bisexual Nonfiction • #1 NEW YORK TIMES BESTSELLER • From Samantha Irby, beloved author of We Are Never Meeting in Real Life, a rip-roaring, edgy and unabashedly raunchy new collection of hilarious essays.

“Stay-up-all-night, miss-your-subway-stop, spit-out-your-beverage funny.... irresistible as a snack tray, as intimately pleasurable as an Irish goodbye.” —Jia Tolentino

Irby is forty, and increasingly uncomfortable in her own skin despite what Inspirational Instagram Infographics have promised her. She has left her job as a receptionist at a veterinary clinic, has published successful books and has been friendzoned by Hollywood, left Chicago,…


You might also like...

Dormice & Moonshine: Falling for Slovenia

By Sam Baldwin,

Book cover of Dormice & Moonshine: Falling for Slovenia

Sam Baldwin Author Of For Fukui’s Sake: Two years In Rural Japan

New book alert!

Why am I passionate about this?

Author Author Snow lover Fish out of water Traveller

Sam's 3 favorite reads in 2023

What is my book about?

When two brothers discover a 300-year-old sausage-curing cabin on the side of a Slovenian mountain, it's love at first sight. But 300-year-old cabins come with 300 problems.

Dormice & Moonshine is the true story of an Englishman seduced by Slovenia. In the wake of a breakup, he seeks temporary refuge in his hinterland house, but what was meant as a pitstop becomes life-changing when he decides to stay. Along the way, he meets a colourful cross-section of Slovene society: from dormouse hunters, moonshine makers, beekeepers, and bitcoin miners, to a man who swam the Amazon, and a hilltop matriarch who teaches him the meaning of being 'priden'.

Struggling with Slovene, a language with grammar so complex it can cause brain damage, and battling bureaucracy, he explores the culture and characters of this underappreciated ex-Yugoslav republic, its wild beauty, and its wild animals.

A love letter to Slovenia, this rare, adventurous account follows a foreigner trying to build a new life — and rebuild an old house — in a young country still finding its own place in the world.

Dormice & Moonshine: Falling for Slovenia

By Sam Baldwin,

What is this book about?

'Charming, funny, insightful, and moving. The perfect book for any Slovenophile' - Noah Charney, BBC presenter

'A rollicking and very affectionate tour' - Steve Fallon, author of Lonely Planet Slovenia

'Delivers discovery and adventure...captivating!' - Bartosz Stefaniak, editor, 3 Seas Europe

When two brothers discover a 300-year-old sausage-curing cabin on the side of a Slovenian mountain, it's love at first sight. But 300-year-old cabins come with 300 problems.

Dormice & Moonshine is the true story of an Englishman seduced by Slovenia. In the wake of a breakup, he seeks temporary refuge in his hinterland house but what was meant as…


5 book lists we think you will like!

Interested in middle-aged women, Washington state, and quality of life?

11,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about middle-aged women, Washington state, and quality of life.

Middle-Aged Women Explore 23 books about middle-aged women
Washington State Explore 73 books about Washington state
Quality Of Life Explore 26 books about quality of life