11 Books That Destroyed Me~In Which There Is Much Weeping And Gnashing Of Teeth

Greetings, world!

There are many different kinds of books out there. For instance, some books make you laugh, (at least on the inside) and other books make your brain hurt. Some books are bubbly and fluffy and make you feel warm and fuzzy inside.

Some books take hold of your heart and proceed to mercilessly pulverize it.

There are books in all of these categories that I love. But today I am going to talk about some of my favorite books in the Heart Crushing category. These are the most fun, aren’t they?

Haha, no.

But I am sure that all of you would love to share my suffering! How, you ask, can I possibly join in on the anguish???

Never fear! I have compiled a nice little list of books that crippled my poor heart, in the hopes that you will be inspired to read them as well.

1. Ender’s Game by Orson Scott Card

Earth has already been attacked once, and we’re not going to let it happen again. I can’t say the same for my traumatized heart.

Ender is a child who has been messed with since before he was even born. He literally exists to be a weapon for the government but he is a CHILD and he needs someone to hug him.

The problem is that he’s so messed up he would probably kill you if you attempted to hug him, but that’s just proof that he needs it.

Ender is tormented by his brother, his teachers, and his own mind. He faces isolation and life-threatening situations and leadership positions before he is eleven years old.

He has a desperate need to win, to pulverize his enemy, but really he just wants to see his sister.


2. A Separate Peace by John Knowles

Gene has a deep-set envy of his best friend Phineas, but he doesn’t even realize it.

Talk about depressing.

This book didn’t so much crush my heart as it did smother it with damp and slightly mildewed towels.

It’s a good book. It’s well written, and the characters are complicated, interesting human beings. I really felt like I got inside of Gene’s head. I felt like IΒ was Gene.

Which is possibly why I felt genuinely depressed after reading this book.

The story is set at a boarding school in New England, so think Dead Poets Society. But more depressing.

3. The Boy in the Striped Pajamas by John Boyne

Bruno doesn’t understand what is going on. At all.

But this is not The Lego Movie. This is the Holocaust, so if you don’t think everything ends in anguish you are dead wrong.

This book is masterfully crafted. It is about World War II, but it is from the unique perspective of the young son of one of the German officers. It is amazing how much the author is able to reveal to us through the eyes of a little boy who doesn’t understand most of what he’s seeing.

As the reader, you understand much too well.

It is a poignant story of friendship in war, with plenty of devastation for all.

4. Harry Potter and the Deathly Hallows by J.K. Rowling

Okay, so technically this book isn’t really as heart-wrenching as some of the others, but as a twelve year old reading this for the first time I WAS NOT PREPARED.

This is the last book in the Harry Potter series, and J.K. Rowling has really developed her characters a whole lot by now. It’s quite impressive how real they all feel. You actually care about them and don’t want them to die.

Ha. Ha ha.

This is literally the only book that I’ve ever read that had me sobbing on the floor. Maybe I was really tired that day, I don’t know. But that definitely happened.

5. The End by Lemony Snicket

Another book you maybe weren’t expecting to be on this list.

The first time I read this as a ten year old I was as cool as a cucumber (aside from being bitter about how it ended) but as a twenty year old reading it for the second time I WAS NOT PREPARED.

I got way too attached to the Baudelaire orphans the second time around. I took this series way too seriously.

Thus, upon reaching the armchair where the three dying siblings huddled together to read a book written by their parents I just about lost it.

Also the baby! Somehow that whole thing meant a lot more to me the second time. I am a huge sucker for the redemption of tragedy through the life of a child for some reason. This essentially happens in Harry Potter too (TEDDY) and I LOVE IT.

6. All the Light We Cannot See by Anthony Doerr

This book…shattered me.


Set during World War II (again), this book follows the stories of Werner, a German boy, and Marie-Laure, a French girl. Werner joins Hitler Youth and Marie-Laure helps the resistance when her city is occupied by the Germans. Needless to say, they both experience the war in radically different ways.

The writing style is rich and full of imagery. The juxtaposition of the contrasting stories is fascinating. Marie-Laure and Werner are both wonderful characters, but Frederick (Werner’s friend) and Jutta (Werner’s sister) are the ones that break my heart and traumatize me to this very day.

It’s too terrible to think about. But sometimes I do anyway just to screw up my brain.

7. The Book Thief by Markus Zusak

Yet another World War II backdrop.

First, I fell in love with the writing style. It is so striking and unique, and undoubtedly effective. It’s teeming with imagery and encompasses all the senses. It’s light and dense at the same time, like poetry. It’s hard to describe.

Then I fell in love with the characters: Liesel, Rudy, Rosa, Hans, Max- they took hold of me, and they wouldn’t let go.

Then the heart crushing happened.

8. The Perks of Being a Wallflower by Stephen Chbosky

I have issues with this book, but Charlie is amazing and I love him.

Charlie is entering his freshman year of high school.

That right there should let you know how depressing this is going to be.

This book is chock full of abusive relationships. People trying to relate to each other in all the wrong ways. It’s desperately sad. We are all yearning for love so much that sometimes we subject ourselves to horrible things in order to get it. We will do whatever we can to belong.

It’s messy. It’s painful. It’s full of stuff that I’m not comfortable reading, but the characters are so real and so heartbreaking that I don’t regret reading it.

Charlie is the most sensitive, thoughtful kid imaginable. I couldn’t help but love him. The way he thinks about things is beautiful and sad.

9. Orbiting Jupiter by Gary D. Schmidt


This story totally took my off guard. I don’t know what I was expecting.

But I wasn’t expecting to find a book that shattered my soul and settled firmly into a spot on my Favorite-Books-of-All-Time list.

Jack is an average 6th grader living with his parents on a farm in Maine. They have cows. Joseph, two years older, is Jack’s new foster brother.

Oh, my dear, dear, Joseph.

Joseph tried to kill his teacher. Joseph went to a juvenile detention center. Joseph has a baby daughter that he’s never seen. And now he’s staying with Jack’s family.

I have a sneaking suspicion that this book was purposefully designed to destroy me.

This is one of the only books that has ever made me cry. It was a bit of a delayed reaction though. I finished the book on Friday, walked around in shock for a couple days and finally cried my heart out on Sunday morning. I knew I was crying for the book, even if it was late. It was weird.

10. Till We Have Faces by C.S. Lewis

Ugh, this book takes everything inside me and mixes it up in a blender. FEELS GREAT.

C.S. Lewis decided to retell the Greek myth of Cupid and Psyche, from the perspective of Psyche’s older sister, Orual. This should be fun.

The story is set in the primitive kingdom of Glome, where they worship Ungit (Aphrodite) and everything is pretty much a nightmare. There is so much darkness and oppression. It’s suffocating to read about at times.

Parts of this book make me feel yucky but it’s SO GOOD. C.S. Lewis really delves into Orual’s, um, well, psyche. It’s disconcerting how much I resonated with Orual’s thoughts and feelings sometimes. She is such a conflicted, broken character.

She cracks open my heart and crawls inside. I became Orual in the same way that I became Gene. But this book, though heavy, is notΒ quite as depressing as A Separate Peace.

11. The Return of the King by J.R.R. Tolkien

In my opinion, this story has one of the most unbearably bittersweet endings of all time. I love it so much.

I’ve read this…five or six times now? And I always cry at the end. Without fail. It’s kind of weird. I think, “Well, this time I probably won’t.” And then I do.

There is a very deep and special place in my heart for the hobbits. When my darling Shire lads get emotional, I just can’t help but get emotional too.

They’ve finished the quest. The Ring is gone. They’re picking up the broken pieces of their home, but there are some things that are broken beyond repair. There are some things we have to let go.

Letting go is so hard.

In Conclusion

Sometimes books penetrate deep inside of us, and it is a beautiful thing. I love it when a book resonates with me and unlocks the emotions that are pent up inside of me. Sometimes it’s a relief and sometimes it’s hard. Sometimes I cry and enjoy being torn apart by the characters, and other times I feel kind of icky and I’m forced to think about troubling matters while my heart squeezes painfully in my chest.

How do books manage to do these things to us?

Your turn! What books caused you to become emotionally compromised? Have you ever cried while reading a book? Do you like books that make your heart feel like it went through a blender? Have you read any of the books I mentioned, and did any of them destroy you like they destroyed me? Let’s weep together!


22 thoughts on “11 Books That Destroyed Me~In Which There Is Much Weeping And Gnashing Of Teeth

    1. Yeah, I get that. I have read hundreds of books and only three on the planet have made me cry, so it’s kind of a weird thing. Also I think I have started crying more as I get older for some reason? Not sure why that is. But things that didn’t used to make me cry make me cry now.


      1. Before Les Mis: with Wicked in my life- I knew a musical song could be sad. I thought I knew how much a musical song could affect you.

        Turns out I was so wrong. Les Mis challenged everything. I realized that in the past, I was 100% blind to heartbreak: Les Mis introduced me to that. The emotions in Les Mis impacted me in a way that emotions in musicals never did before. I never was an emotional wreck watching a musical- Les Mis still has its hold on me- it still does it

        Liked by 1 person

  1. I’ve definitely read a bunch of these or at least heard of some. I have yet to read Ender’s Game or finish one of the series mentioned above.

    The only book that has ever made me cry was The Kite Runner. I think another book might have made me cry but I really don’t remember *shrugs* I tend not to have strong feelings, I guess.

    Also, weeping and gnashing of teeth? Wow, must’ve been intense then xD

    Liked by 1 person

    1. Oh, I have never read The Kite Runner, but I am curious now.
      Haha, it’s possible I am exaggerating a bit. πŸ˜‰ I mean, as much as these books destroyed me, only three out of eleven actually made me cry. Mostly I guess it’s just inner turmoil. I actually feel like I have gotten more emotional as I get older, and that feels kind of scary. I used to laugh at my mum because she cried at random movies, but I have started doing that a bit myself now. It’s weird.
      Also I have read a lot of really emotional books that haven’t made me feel anything AT ALL.

      Liked by 1 person

  2. The Lord of the Rings broke my heart at the end and still smashes it into slightly smaller pieces each time (I don’t actually cry, but I stare at the ceiling like a moody teenager instead).
    A Tale of Two Cities and Cry, the Beloved Country are top of my heart-crushing book list. Both the endings are so bittersweet and all the characters are miserable and it hurts. 😦
    Another would be Fahrenheit 451. There’s so much emotion in that tiny book that it feels like a slap in the face… but in a good way???
    Yet another reminder to read Ender’s Game. One day I might actually get to it!
    Great post! Yeah, heart-crushing’s the most fun.

    Liked by 1 person

    1. I KNOW. The ending of The Lord of the Rings is beautiful.
      Yes, A Tale of Two Cities is another good one! I think I read Cry, the Beloved Country, but…I don’t remember anything about it. It was a long time ago. Bittersweet endings are my FAVORITE.
      I have heard a lot about Fahrenheit 451, but I haven’t actually read it yet. I would love to get slapped in the face though!
      Thank you! I enjoyed writing it!

      Liked by 1 person

    1. Sometimes it’s weird how much we enjoy being torn apart? But I wonder if maybe it can be therapeutic at times. I don’t know.
      Well, if I convinced you to read any of the books on my list, my job here is done. πŸ˜‰
      I haven’t read any of the books you mentioned, but I might have to look them up now!
      Thanks so much for stopping by!


  3. I’ve read Ender’s Game, The Boy in the Striped Pajamas, All the Light We Cannot See, and The Book Thief, and agh, I wish I could say otherwise, but none of the hit me internally. I do like books that do crazy and strange things to my heart, but if I think about, I don’t think a book has ever messed with me in a way that has left me sad. If something terrible or tragic happens in a book, it doesn’t give me a gut reaction like seeing it would. It’s the emotional moments between characters that gets to me, and not necessarily emotionally sad ones too. The part in Fish in a Tree that has made me cry everytime isn’t even sad. It’s closer to the happy end of the things.

    Liked by 1 person

    1. Yeah, it’s weird how some books just gut-punch some people and not others. There’s this book Code Name Verity that completely floored my friend, but I hardly felt an thing when I read it, even though I could tell it was supposed to be emotional. And I didn’t dislike it either. It just didn’t “get to me.”
      Happy moments can definitely effect emotionally as well! Actually with some of these books that I mentioned it’s a mixture of happy and sad that does it. Bittersweet moments are really what cause my emotions to keel over. Because usually a moment isn’t truly happy unless it’s on the other side of pain. And that’s what breaks my heart. If a book is all happy all the way through, I’m just not going to care. It’s the relief of coming out of the storm that can make me break down. If a book ends totally depressing I am much less likely to cry.

      Liked by 1 person

      1. Oh yes, I’ve read Code Name Verity. I think I was in between you in your head on how much it got to me.
        Yes- the sad and happy combinations, that’s it. To be more specific, I’ve realized it’s the moments between characters when they’re loyalty and love is shown that create tears immediately. Yes, I agree with that too. Very happy books and dark books (not that I read the latter very often) aren’t likely to make me cry.

        Liked by 1 person

  4. I can’t read the Boy In Striped Pajamas because someone spoiled it for me. Even though it’s a really obvious ending, I don’t want to go through it.
    I love Adam Silvera’s books, I love the way he handles death. Not a lot of people explore it fully, possibily because they don’t want people to cry all the time.

    Liked by 1 person

    1. Yeah, when you KNOW how awful something is going to be, it can be hard to take the plunge- it’s best to plunge blindly! (Haha, that sounds terrible, but with reading it’s true.)
      Ooh, I have heard of Adam Silvera but I haven’t read any of his books. Now that I know he explores death I may have to reconsider him.
      Why wouldn’t you want people to cry all the time??? πŸ˜‰

      Liked by 1 person

  5. I’m not actually one of those people that cry when they feel super sad (I’m a “let’s get angry and then cry a lot” certain of person) so I rarely cry in novels, but I do sometimes just stop reading and lie on the floor and question existence. Return of the King definitely makes me do that, as does Les Miserables and A Tale Of Two Cities, and um…all those other books as well? John Boyne wrote another book called Stay Where You Are And Then Leave, which I read a few months ago. it was okay (about a little boy whose father is a mental hospital after being shellshocked on the Western front), but I didn’t feel particularly overwhelmed by it.

    Liked by 1 person

    1. I get angry sometimes too. I think I used to get angry more, but the older I get the more weepy I get for some reason? I’m not sure why. Oh, Les Miserables and A Tale of Two Cities! I knew I had forgotten to add something to this list. Those ones definitely got to me. I didn’t cry though. That’s seriously only happened three times.
      I kind of like the title of that John Boyne book you mentioned.
      Thanks for your thoughts!

      Liked by 1 person

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