These are the best books about what it means to be male

Are you desperately wondering how to define masculinity in this day and age? Well, these books may help you on your quest for answers...

What does it mean to be male? It’s a question many philosophers, academics and authors have been asking for centuries; and the real answer, gents, is that no one actually knows. We live in a constantly shifting, changing world (thank goodness). Gender dynamics are (rightfully) ever transforming, and our place in the world is perpetually in flux; which means the concept of ‘maleness’ is hard to pin down to any sort of exact science.

There are some authors, though, who can provide a valued insight into the male psyche. Through both poignant fiction and observant non-fiction, there are some books out there that have fully captured what it means to be a man living on the planet; whether centuries ago or today, whether a brief snapshot of a specific age or a journey through an entire male lifespan. Read on; and see what you can learn about being a gentleman from these uniquely documented male experiences.

Sweet Sorrow by David Nicholls

You’ll already know all about David Nicholls, of course; he’s the man behind the One Day fame, about which we’ve waxed lyrical previously. But have you read his latest bestseller? The epitome of a coming-of-age story, it focuses on 18-year old Charlie Lewis, and mostly takes place in the summer immediately preceding Charlie’s A-level exams.

When we first meet Charlie, he’s struggling. His exams did not go according to plan, and he has no idea what the future will hold. But when he inadvertently (and unexpectedly) stumbles into performing in a local outdoor Shakespeare production of Romeo & Juliet, he meets Fran Fisher; and his world is promptly turned upside down. As Charlie gains confidence in himself, he simultaneously falls in love; and the result is a deeply moving tragicomedy that depicts what it is to be a teenage boy in love for the first time.

David Copperfield by Charles Dickens

Well, we said we’d span the centuries; so this is us following through on that promise. If you’ve never read David Copperfield, it might be time to clear some space on your bookshelf; not only is it a brilliant insight into the male psyche, but Dickens actually admitted it was his favourite of all his books. How’s that for a recommendation?

It’s semi-autobiographical, and follows Copperfield’s life all the way from his miserable childhood to his successful middle age years as a prolific author. Copperfield is one of the most famous male characters ever depicted in literature, and the book is also jam-packed with some of Dickens’ most famous literary character creations: Betsey Trotwood and Uriah Heep among them.

The Perks of Being a Wallflower by Stephen Chbosky

It’s another coming-of-age story, this time set in America; and it’s one that every gentleman should make it his mission to read. It’s a brilliant, moving, poignant insight into what it’s like being a freshman at an American high school. It centres on the story of Charlie, who is deeply shy, socially awkward and exceptionally intelligent.

He’s trying to explore the world in which he lives, while simultaneously fighting a desire to run away from it. He explores the world through pop-culture — it’s the 90s, so Charlie lives in a world of mix-tapes and the Rocky Horror Picture Show — but before long, he recognises that he can’t experience everything he longs to while watching from the sidelines. Sure to transport any gentleman back to those tentative, trepidatious schooldays, it’s a masterpiece and a must-read.

These are the best books about what it means to be male

The Perks of Being a Wallflower


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Less by Andrew Sean Greer

If you’re not already aware of him, Andrew Sean Greer truly is a writer to watch. Actually, you don’t even need to watch him any more; his star has already risen, and we’d highly recommend snapping up this book as fast as you can. It tells the story of Arthur Less, a 49-year old writer whose career is in a downward spiral, and whose ex-boyfriend is getting married.

So Less decides to take a tour around the world, determined to remove himself from the vicinity both of heartbreak and a floundering career. Follow Less around the globe, from Paris to Berlin to India; and prepare to laugh out loud as you simultaneously get a refreshing reminder of the power of hope even in the most despairing of circumstances.

Notes on a Nervous Planet by Matt Haig

Male mental health is something we all need to be talking about more; and there is arguably no greater voice on the topic than bestselling author Matt Haig. We’ve extolled the considerable virtues of his memoir, Reasons To Stay Alive; and this later book is the handbook every gentleman needs to feel happy in our fast-paced, technologically saturated world.

Haig is no stranger to anxiety, panic attacks and depression; and in this book, he takes a look at the surrounding forces that could have impacted that. He looks at how we can stay balanced in a world which encourages us to be dissatisfied and in which it’s normal to worry about anything and everything; and he’s full of advice on how we could all strive to live happier, healthier and calmer lives.

These are the best books about what it means to be male

Notes on a Nervous Planet


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Stoner by John Williams

So many books focus on those who live vibrant, exciting, innovative lives — and where male characters are concerned, we’re often presented with those who do phenomenal things, or to whom phenomenal things happen. It can be a tad dispiriting to read about all those wildly exciting lives happening in literature; but this book offers a different perspective on what makes for a meaningful existence.

William Stoner doesn’t live a remarkable life. He’s not the sort of chap many people remember after he’s gone. But the novel explores the beauty that can be found in the simplicity of individual lives, through tracking Stoner’s last minute career change from agriculture to teaching English, and through his marriage to the wrong woman: and it’s a glimpse into all those events that so often pass unrecorded, but which are no less noteworthy for that.

Me Talk Pretty One Day by David Sedaris

Put simply, any book by David Sedaris will be a brilliant (and side-splittingly funny) insight not only into the male psyche, but into any psyche at all. Sedaris’ observations of the world in which we live, and of human beings, are as precise and nuanced as they come; and his prose is so acerbic and razor sharp that writers everywhere lie awake at night wondering how they can match his wit.

If we were forced to pick one of his books, though, it would be this one: a collection of essays tracking Sedaris’ move to Paris from America, and his attempts to learn French. While the book is primarily about Sedaris’ desire to learn something new and his observations of the new culture in which he finds himself, it’s also a satirical commentary on his life, and on modern life. It’s safe to say this is a book from which every gentleman can learn more than a little something — and have more than a few laughs along the way.

These are the best books about what it means to be male

Me Talk Pretty One Day


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Fleishman Is In Trouble by Taffy Brodesser-Akner

Ever struggled to navigate dating apps? Well, so has protagonist Toby Fleishman: as we see at the very beginning of this sharp, acerbic novel that will, by the end, leave you feeling a little as though you’ve been struck by lightning (in the very best way). Toby starts the novel as a newly single, co-parenting ex-husband, with what seems like a date every other night and an apparently inexhaustible dating app profile.

But when his ex-wife, Rachel, disappears, Toby has to change his lifestyle (and fast), to give his children the care they need while trying to work out where on earth she could have gone. What follows is a shift from biting comedy to a book centering on gender politics; and it ends as a trailblazingly feminist novel that necessitates Toby exploring his part in the downfall of his marriage. It’s a fascinating exploration of trying to navigate dating apps while juggling other responsibilities; and it encourages all of us to look at our own wrongdoings.

These are the best books about what it means to be male

Fleishman Is In Trouble


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So You’ve Been Publicly Shamed by Jon Ronson

We live in an era of ‘cancel culture’; how often have you vowed to boycott a particular creative’s work because of toxic behaviour on their part, or seen others doing the same thing in a storm of Twitter furore? It’s a form of public shaming; and that’s what Jon Ronson explores in this seminal book.

Ronson is, unequivocally, one of the wittiest, most observant writers of our time — and he delves into a 21st century phenomenon that explores what it means to be visibly shamed in our online era; something that has the potential to affect all of us in some way. For anyone trying to work out what it means to be male today, this is a book you won’t want to miss; not because public shaming is a uniquely male phenomenon, but because public shaming and cancel culture is a universal, all-encompassing part of modern life that’s very much here to stay.

These are the best books about what it means to be male

So You've Been Publicly Shamed


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The Descent of Man by Grayson Perry

If there was a definitive book written on masculinity, this would be it. With his trademark humour, he explores what it means to be a good man today; would sort of men would make the world a better place for all who live in it; and what would happen if we redefined what masculinity — and what being a man in today’s world — really means.

The result is a funny, prescient, salient book about the stereotypes surrounding masculinity, and how those stereotypes can be thrown off to create greater happiness for men and women, and to drive gender equality forwards. Perry freely admits he’s not immune from these stereotypes himself; and his refreshing honesty makes the book all the more relatable. It’s an essential read for those looking to define what it means to be a man today; and for anyone who wants to do their bit to make the world an infinitely better place.

Looking to give your eyes a break from all that reading? Why not go and listen to some jazz at Ronnie Scott’s

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