16 Heartbreaking Books That Will Emotionally Wreck You

Room by Emma Donoghue

This is a haunting story about a woman held captive in a shed for years with her five-year-old son. She tries to teach him and entertain him in their tiny room until they have a chance to escape. This is an unforgettable pick from books that will emotionally wreck you.

Following their escape, they find acclimating to normal life to be challenging, especially for the little boy. This story will pull on your heartstrings and leave you in tears.

Even though the saying is “the book is better”, the movie adaptation of this contemporary fiction book was really good. There are only a few other book adaptations I would add to that list. If you haven’t read this book about motherhood yet, you need to add it to your list.

Push by Sapphire 

Push is a look at life in the poverty-stricken streets of Harlem in the eighties. The main character is an illiterate 16-year-old pregnant with her second child by her father.

The commentary on a life of poverty and the struggles to get out of her situation are horrific but inspiring. It is incredibly difficult, but such a worthwhile read.

The One Hundred Years of Lenni and Margot by Marianne Cronin

GET READY TO UGLY CRY. This book wrecked me. This is the story of 17-year-old Lenni, who has terminal cancer, and her art partner, 83-year-old heart patient Margot.

They connect at the end of Lenni’s life in the hospital art therapy room where they decided to paint a picture for every year of their combined 100 years.

While painting their picture, we get to learn about their lives before their illnesses and witness an incredible bond form. The ripple effects of their bond and friendship took my breath away numerous times.

Truly one of the best books I’ve read in a long time. This one needs to go on our list of books to emotionally wreck you.

Hearts Invisible Furies by John Boyne

Cyril Avery is not a real Avery- this is what his adoptive parents tell him.  Cyril is born to a young woman out of wedlock and is adopted by a rich family in Dublin. 

He spends his life coming to know himself and who he wants to be.  This is a touching and heartfelt story from the first page to the last. Even though this book is well over 500 pages, it didn’t feel long while I was reading it. This is definitely one of my favorite long books that will emotionally wreck you. This is a beautiful LGBTQ book.

Where the Crawdads Sing Deluxe Edition by Dehlia Owens

September 2018 Reese Witherspoon Book Club Pick

I will admit when I saw the description of this book, I was not sold.  A trusted individual, who has never steered me wrong in the past, gave me an advanced copy so, I took the leap.  And wow, am I glad I did.  I read this book and then recommended it to everyone I knew. 

This 70s book has that spark, that special something that makes it extra.  It is no surprise that we chose this as our favorite of 2018.

We have an entire post dedicated to this book and how to host a book club around it which makes it a perfect book for book clubs! If you love this book, check out our list of 13 books like Where the Crawdads Sing.

The Map of Salt and Stars by Jennifer Zeynab Joukhadar

This book is about Syrian life and a modern-day refugee seeking safety.  The story is spliced in with another taking place centuries before – a mythical adventurer looking to learn the map-making trade. War-torn Syria is hard to read about, but the mapmaker’s tale helps lessen some of the heavier moments.

You will be rooting for both heroines in this moving tale destined for our list of books that will emotionally wreck you.

The Kite Runner by Khaled Hosseini

This book set in the 70s in Afghanistan is one of the most emotional books I’ve ever read. I sobbed for a full 30 minutes after the last chapter. The story of the friendship between a wealthy boy and his servant is one filled with betrayal, tragedy, and heartbreak.

Told against the background of Afganistan’s destruction and the war, this sweeping tale is a must-read if you are looking for books that will emotionally wreck you.

Refugee by Alan Gratz

Three tales in one, the book is told in alternating chapters by three narrators.  The stories feature Josef, a Jewish refugee fleeing WWII Germany, Isabel a Cuban girl on her way to Miami in 1994, and Mahmoud a Syrian refugee seeking asylum in Germany in 2015. The chapters rotate between the three characters and their stories do connect at the end in a meaningful and moving way.

The characters are all about 13 years old but shoulder burdens that would be hard for an adult to handle. Gratz accurately portrays each child’s struggle with both grace and clarity – not shying away from difficult emotions and even death. If you love this YA historical fiction book, we have a list of Powerful WWII Books for Kids.

Night by Elie Weisel

I have a personal story about this book.  My husband’s grandmother grew up in the same town as Elie Weisel.  She knew both him and his wife.  This was the first thing that she told me when I met her (My husband’s name is also Elie but this is purely coincidental). 

This is a must-read non-fiction book about the Holocaust written by the winner of the Nobel Peace Prize.  It is a short but very powerful book that will emotionally wreck you. For more amazing Oprah’s Book Club Picks, you can see the full list.

The Day the World Came to Town by Jim DeFede

I sobbed through this entire story. This non-fiction book was poignant and hopeful at the same time. I loved learning about the town of Gander, Newfoundland and how they took in 6,500 people on planes that had to have emergency landings after 9/11.

The townspeople were so welcoming and kind. It’s like Mr. Rodgers says – always look for the helpers.

A Child Called It by Dave Pelzer

Probably the most graphic novel on our list, this memoir details a young boy’s severe child abuse case. It is incredibly hard to stomach the things the author experienced. That anyone could do that to a child is heartbreaking and disgusting.

This book is deeply disturbing and like Push is not for the faint-at-heart.

The Time Traveler’s Wife By Audrey Niffenegger

Clare and Henry have an unusual love story. They’ve known each other since Clare was six and Henry was thirty-six, but got married when Clare was twenty-three and Henry was thirty-one. You see, Henry is an adventurous librarian who inadvertently travels through time.  

I adore how this story explores very real challenges that any couple faces. With the added time travel element, it becomes an unforgettable pick from our list of romance books. The way that they fight for their love gives this book its clear spot on our list of best romance novels of all time. But be warned, this book may emotionally wreck you.

While I realize there is only the loose librarian connection to this book list, Henry and Clare’s story is one of my all-time favorites and it shouldn’t be missed. You can find more books like this on our list of 23 of the Best Time Travel Books Like the Time Traveler’s Wife.

Castle of Water by Dane Huckelridge

This is a wonderful contemporary fiction book about love and survival.  It is so much more than it appears on the surface.  It’s a beautifully written book about a vacation gone awry.

When Sophie and Barry find themselves on an Island as the sole survivors of a plane crash, they learn to depend on each other.  The book moves seamlessly from the past to the present, weaving an intricate tale. It’s one of Kirsten’s favorite books of all time. We also included this one in our list of feel-good books!

If you are looking for vacation books, this is a perfect pick from the list of books like People We Meet on Vacation.

Me Before You by Jojo Moyes

Me Before You has quickly become a classic story – and a movie to boot. But beware! This is one of the books that will emotionally wreck you that you don’t want to read in public!

When a young man becomes paralyzed his parents hire a young woman to be his companion. As love blooms, and she tries to convince him that life is still worth living, the reader questions what they would sacrifice to make a loved one happy. This novel about grief deals with grieving before the person has passed.

Always, in December by Emily Stone

I was blown away by this tear-jerking story. It was a romance story for the first 30% of the book, but then it becomes something much deeper.

Josie mails a letter to her deceased parents every Christmas, but this Christmas she accidentally hits a stranger named Max with her bike on the way to the post box.

As she explored the holiday season with Max her feelings start to grow, but when he leaves unexpectedly, she’s left to deal with the aftermath of the impact he had on her heart. But fate isn’t done with their story yet as they bump into each other throughout the year.

Probably my favorite Christmas book of 2021, this one is a tear-jerker for sure. I sobbed for the entire last 10% of the book and it will most likely, emotionally wreck you. This book is a testament to the healing power of love and the kind of impact each of us can make on each other.

I don’t want to spoil anything, but if you are looking for a Christmas book that ends with a bow and smile, you may want to look elsewhere.