The best books with realistic female friendships in challenging times

Who am I?

I’d thought I was writing a novel about someone putting a life back together after everything fell apart but, when I’d finished, readers told me I’d written a book about vivid, authentic friendships. It was a welcome surprise. From Charles Dickens to Sylvia Plath, nuanced characters have always interested me and so, when writing, I set myself the task of believable dialogue and interactions which readers can relate to like it’s their own friends sitting around a table; laughing, crying, or bickering. When a life falls apart it’s often friendships that are tested to breaking but then become stronger as a result.


I wrote...

Keep Walking, Rhona Beech

By Kate Tough,

Book cover of Keep Walking, Rhona Beech

What is my book about?

Rhona’s candid, messy journey will make you laugh, cry and remember. Not a typical break-up book, it's much more profound. Rhona has been casually swapping one job for another while comfy in a long relationship, until it ends abruptly and her efforts to adapt to that change are thrown by unwelcome news... 

This beautifully written, pacey satire about female friendship, heartbreak, career change, conceiving and illness will appeal to fans of Fleabag. Join Rhona on a laugh (and cry) out loud search for meaning amongst the bars, offices, and clinics of Scotland. Will her friendships survive the challenges? Will she survive? At once funny and tender, Keep Walking, Rhona Beech is a clear-sighted look at a generation that was told they could have it all.

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

The books I picked & why

Book cover of Cranford

Kate Tough Why did I love this book?

It’s never the plot that draws me to a novel; it’s always other ingredients like people and place and, in these regards, Cranford is a stellar delight. The protagonist is a frequent house guest in the small town of Cranford, giving readers intimate access to the quirky social codes of its mostly female population. From the ones who care about social mores to the ones who care less, these wonderful vignettes document their attempts to outwit a visiting magician, or foil rumored night-burglars, or adapt to the losses of loved ones. Each woman has had a journey in some way stifled by the patriarchy of the 1800s but these ladies’ timeless and absorbing intelligence, compassion, loyalty, ingenuity, forbearance, and above all, wit, shine through.

By Elizabeth Cleghorn Gaskell,

Why should I read it?

2 authors picked Cranford as one of their favorite books, and they share why you should read it.

What is this book about?

Elizabeth Gaskell was a British author during the Victorian era. Gaskell's novels are notable for detailed descriptions of the different classes of society in 19th century Britain. Cranford is a novel about a fictional town modeled closely after one Gaskell was familiar with. The story features a series of episodes in the life of Mary Smith.


Book cover of Conversations with Friends

Kate Tough Why did I love this book?

Of all the genres, I’m drawn most to contemporary realism and this book is a spectacular example. Despite the age gap between myself and the main character (Frances, aged 21) the writing is so astute, assured, and insightful that this book has no problem straddling the generations. Friendship definitions herein are not conventional which makes it infinitely interesting; the four main characters are a mix of best friends, exes, spouses, new friends, new flings, and new infatuations. Their daily concerns and communications are utterly contemporary, reflecting the seamless mish-mash of digital and in-person updates that sustain modern connections. Vulnerability is no one’s strong suit, so when these self-aware, funny and flawed pairs meet they burn brightly until they burn out. 

By Sally Rooney,

Why should I read it?

2 authors picked Conversations with Friends as one of their favorite books, and they share why you should read it.

What is this book about?

***NOW ON BBC THREE AND iPLAYER***

'This book. This book. I read it in one day. I hear I'm not alone.'
- Sarah Jessica Parker (Instagram)

'Brilliant, funny and startling.' Guardian

'I really like Conversations with Friends. I like the tone [Rooney] takes when she's writing. I think it's like being inside someone's mind.' - Taylor Swift

'A sharp, darkly funny comment on modern relationships.' Sunday Telegraph

Frances is twenty-one years old, cool-headed and observant. A student in Dublin and an aspiring writer, at night she performs spoken word with her best friend Bobbi, who used to be her girlfriend.…


Book cover of Another Brooklyn

Kate Tough Why did I love this book?

This book was a powerful reminder of how capable our younger selves are and how much wiser, at times, than the adults around us. The poetic prose quality had me hooked and the wistful truth that some of our most defining friendship bonds are temporary. Evoked in lucid, beautiful sentences the vital, essential connections between August, Sylvia, Angela, and Gigi usher the group through adolescent challenges in a tough neighbourhood. On the streets of Brooklyn in all seasons the young teenagers rely on each other as they hone their skills to negotiate life’s harsh realities away from their parents’ gaze. It’s a process that turns out better for some than others but they carry a part of each other wherever life takes them. 

By Jacqueline Woodson,

Why should I read it?

3 authors picked Another Brooklyn as one of their favorite books, and they share why you should read it.

What is this book about?

THE NEW YORK TIMES BESTSELLER FROM A NATIONAL BOOK AWARD WINNING AUTHOR

A TIME MAGAZINE TOP 10 NOVEL OF 2016 | SHORTLISTED FOR THE NATIONAL BOOK AWARD FOR FICTION 2016

FROM THE WINNER OF THE ASTRID LINDGREN MEMORIAL AWARD 2018

They used to be inseparable. They used to be young, brave and brilliant - amazingly beautiful and terrifyingly alone. August, Sylvia, Angela and Gigi shared everything: songs, secrets, fears and dreams. But 1970s Brooklyn was also a dangerous place, where grown men reached for innocent girls, where mothers disappeared and futures vanished at the turn of a street corner.

Another…


Book cover of Rules of Civility

Kate Tough Why did I love this book?

Although dipping into glamorous strata of New York society, the friendship dynamics reminded me of the period of adulthood where you start to make your way in the world… Often it involves new jobs or new cities and sometimes women discover the people they thought were close friends are not. Parallel journeys of female friends can put them into tension where paths diverge and taking space is the only solution. Here, avid reader Katey is moving beyond her humble beginnings by talent and character alone, while room-mate Eve is escaping her privilege and family ties; their agendas blend well for a while until they spin off in different directions. Resourceful Katey continually starts over in her smart, sharp-humoured style becoming ever more able to rely on herself.

By Amor Towles,

Why should I read it?

3 authors picked Rules of Civility as one of their favorite books, and they share why you should read it.

What is this book about?

From the #1 New York Times-bestselling author of The Lincoln Highway and A Gentleman in Moscow, a “sharply stylish” (Boston Globe) book about a young woman in post-Depression era New York who suddenly finds herself thrust into high society—now with over one million readers worldwide

On the last night of 1937, twenty-five-year-old Katey Kontent is in a second-rate Greenwich Village jazz bar when Tinker Grey, a handsome banker, happens to sit down at the neighboring table. This chance encounter and its startling consequences propel Katey on a year-long journey into the upper echelons of New York society—where she will have…


Book cover of Animals

Kate Tough Why did I love this book?

How are women supposed to behave, discreetly? Are their friendships always a saccharine Hallmark card? Not in this novel. Living loudly, louchely, in chaos, with hedonistic nights out and all-day hangovers, Laura and Tyler are a tight, whip-funny twosome… except one has a wedding on the horizon to a teetotal stable man, and she’s wrestling with whether marriage is a legitimate life milestone anymore. The friendship portrayal here is a messy, clever, and foul-mouthed foray into the moment when inseparable friends face the prospect of their familiar relationship disappearing through the unstoppable forces of adult life. And we’ve all had impossible choices when we haven’t known which loyalties to put first – one’s duty to oneself or to one’s best friend?

By Emma Jane Unsworth,

Why should I read it?

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

What is this book about?

“An utterly triumphant ode to female friendship, in all its intense, messy and powerful beauty” from the internationally bestselling author of Grown Ups (Elle).

It is the moment every twenty-something must confront: the time to grow up. Adulthood looms, with all its numbing tranquility and stifling complacency. The end of prolonged adolescence is near.

Laura and Tyler are two women whose twenties have been a blur of overstayed parties, a fondness for drugs that has shifted from cautious experimentation to catholic indulgence, and hangovers that don’t relent until Monday morning. They’ve been best friends, partners in excess, for the last…


You might also like...

A Long Way from Iowa: From the Heartland to the Heart of France

By Janet Hulstrand,

Book cover of A Long Way from Iowa: From the Heartland to the Heart of France

Janet Hulstrand Author Of A Long Way from Iowa: From the Heartland to the Heart of France

New book alert!

Who am I?

Author Reader Editor Francophile Minnesotan Once and forever Brooklynite

Janet's 3 favorite reads in 2023

What is my book about?

This memoir chronicles the lives of three generations of women with a passion for reading, writing, and travel. The story begins in 1992 in an unfinished attic in Brooklyn as the author reads a notebook written by her grandmother nearly 100 years earlier. This sets her on a 30-year search to find her grandmother’s journals and uncover the hidden interior lives of her mother and grandmother.

Her adventures take her to a variety of locations, from a small town in Iowa to New York, Washington, London, and Paris—and finally to a little village in France, where she is finally able to write the book that will tell her own story, intertwined with the stories of her mother and grandmother.

A Long Way from Iowa: From the Heartland to the Heart of France

By Janet Hulstrand,

What is this book about?

This story, about three generations of women with a passion for reading, writing, and travel, begins in 1992, in an unfinished attic in Brooklyn, as a young writer reads journals written by her grandmother as a schoolgirl nearly 100 years earlier. This sets her on a 30-year quest to uncover the hidden lives and unfulfilled dreams of her mother and grandmother. In this coming-of-middle-age memoir, the author comes to realize that the passion for travel and for literature that has fueled her life's journey is a gift that was passed down to her by the very role models she was…


5 book lists we think you will like!

Interested in best friends, love triangle, and the upper class?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about best friends, love triangle, and the upper class.

Best Friends Explore 83 books about best friends
Love Triangle Explore 70 books about love triangle
The Upper Class Explore 74 books about the upper class