10 Devastatingly Sad Books to Read This Autumn

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If you’re looking for some emotional reads this autumn, these 10 sad books are for you. I’ve included John Green’s classics like The Fault in Our Stars and Looking for Alaska, which always know how to bring on the tears. And seriously, A Little Life is one of the saddest books I’ve ever read. (I really couldn’t pick up any books after reading it for days) These books are filled with love, loss, and heartbreak, perfect for sad girl autumn vibes. Whether you want to cry over a touching romance or reflect on deeper themes, these really, really sad books will have you reaching for tissues.

Sad Books To Read This Fall

My Dark Vanessa by Kate Elizabeth Russell

This book is intense, and it doesn’t pull any punches. It follows Vanessa as she looks back on her teenage relationship with her much older teacher, and the emotional fallout that comes with realizing the truth as an adult. The writing is sharp and uncomfortable in the best way. If you’re looking for sad books that make you emotional and really make you think, this one’s for you.

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The Fault in Our Stars by John Green

It’s the kind of story that lures you in with witty banter and relatable teen drama, then crushes your heart with a deep, emotional love story. Hazel and Augustus’s relationship is beautiful and tragic, and you’ll probably sob your way through the final chapters. (I did!) Green’s writing is both funny and poignant, making it a perfect pick if you want to laugh and cry in equal measure. It’s the ultimate books that make you cry experience, so make sure to grab some tissues before you start the book.

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A Little Life by Hanya Yanagihara

This is probably the saddest book in the list. Seriously, it’s like emotional endurance training. It’s about four friends living in New York, but the real heart of the story is Jude, whose traumatic past is so devastating it will make your heart hurt. The book is long and sometimes feels overwhelming, but the writing is so beautiful you keep turning the pages even though you’re crying half the time. If you’re into really, really sad books that make you sob very badly, A Little Life will wreck you (in a good way).

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If He Had Been with Me by Laura Nowlin

Autumn and Finny have a complicated friendship that might have been something more, but tragedy strikes before they can figure it out. Nowlin captures that teenage longing and “what if” feeling perfectly. It’s the kind of story that will have you thinking about all the missed chances in your own life. I’d recommend this to anyone who loves books that make you emotional, especially if you’re a fan of bittersweet love stories.

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Girl in Pieces by Kathleen Glasgow

Girl in Pieces tackles mental health, trauma, and recovery in such a raw, real way. Charlotte, or Charlie, is dealing with self-harm, homelessness, and loss, and Glasgow doesn’t sugarcoat her journey. It’s tough to read at times, but you can’t help but root for Charlie. If are looking for sad girl autumn books that feel deeply personal and healing, this one is a must-read.

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You’ve Reached Sam by Dustin Thao

Imagine being able to call someone who’s gone. That’s the premise here, and it’s as emotional as it sounds. Julie is grieving the sudden loss of her boyfriend, Sam, but somehow she can still talk to him through his old phone. It’s a beautifully heartbreaking story about letting go and finding closure. The ending? Total tear-jerker. I didn’t think I’d cry as much as I did, but this book sneaks up on you. Perfect for anyone looking for a gentle, sad book about love and loss.

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Me Before You by Jojo Moyes

This book feels like a rom-com until it doesn’t. It’s about Louisa, who becomes the caregiver for Will, a wealthy man who was paralyzed in an accident. Their relationship is beautiful and heartbreaking, and just when you think it might have a happy ending, Moyes drops an emotional bomb. I cried my eyes out at the end, not going to lie. If you love books that make you sob and stories that explore love, life, and difficult choices, this one is for you. Be warned, though—your heart might not recover.

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Reminders of Him by Colleen Hoover

Reminders of Him follows Kenna, a woman who’s trying to rebuild her life after a tragic accident and time in prison. The way Hoover writes about guilt, forgiveness, and redemption is incredibly moving. The love story is tender, but the real heart of this book is Kenna’s journey to reconnect with her daughter. It’s one of those books that make you cry, but also one that gives you hope. Perfect for a cozy, emotional fall read.

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Looking for Alaska by John Green

The story follows Miles as he navigates boarding school life and falls for the elusive and mysterious Alaska. Then tragedy strikes, and it’s devastating. What I loved about this book is how it deals with grief, guilt, and growing up. The characters feel so real, and their pain is so relatable, it’s hard not to get emotional. If you’re looking for a coming-of-age story that makes you reflect on love and loss, this one’s a great pick for sad girl autumn.

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Of Mice and Men by John Steinbeck

Finally, we have a short classics that will tear at your heart. It’s about two drifters, George and Lennie, and their dream of owning land during the Great Depression. Lennie’s strength and innocence lead to a tragic ending that will have you in tears. It’s a short book, but it packs a huge emotional punch. Steinbeck’s writing is so simple yet powerful, and this is definitely a book that will make you sob. If you haven’t read it yet, put it on your list for those days when you’re ready for a truly sad and emotional journey.

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Stephy George
Stephy George

Hi I am Stephy ! I became a bookworm in my late twenties. So I created this little corner of books online to share my love of reading with YOU! I want to help you find the best books to read so you won’t ever have to worry about your next read!

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