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10 of the Most Engaging Books That are Sure to Make You Cry

Books That are Sure to Make You Cry
Those who enjoy reading, consider books to be their friends. True friends that make us happy, and at times, also make us shed tears. For now, here's a collection of some outstanding tomes, bound to make you misty-eyed.
Penlighten Staff
Last Updated: Jun 3, 2018
"The love of learning,
the sequestered nooks,
And all the sweet serenity of books."
- Henry Wadsworth Longfellow
Reading a sad book, quite literally, splits me up into two people. A part that's mad at the author for having written such a heart-wrencher, and the other that wants to kiss the hands that wrote the heart-wrencher. Truth be told, if there is one thing that can make me revel in melancholy, it's got to be a book which gets me teary-eyed.

The list of books that follows is a personal one - these are some of my favorite books that are worth reading over and over again, despite the accompanying tears. It comprises a couple of classics, a little magic, some animal love, and even a Stephen King.
10 Books That Will Make You Shed Tears
F. Scott Fitzgerald's The Great Gatsby
"The exhilarating ripple of her voice was a wild tonic in the rain."
The Great Gatsby is the story of star-crossed lovers set against the backdrop of the roaring twenties. Fitzgerald's moving novel takes us through Jay Gatsby's furiously obsessive love for the delicate Daisy Buchanan, and his ultimate realization that money can take you to the heady heights of power, but never buy love.
Harper Lee's To Kill a Mockingbird
"Mockingbirds don't do one thing but make music for us to enjoy. They don't eat up people's gardens, don't nest in corncribs, they don't do one thing but sing their hearts out for us. That's why it's a sin to kill a mockingbird."
Harper Lee's classic covers racial discrimination, Southern class divides and prejudices in a delicately woven tale seen through young eyes. However, the most inspiring undertone of this book is that compassion should never regard skin color. After all, you never really understand a person until you consider things from his point of view - until you climb around in his skin and walk around in it.
Anne Frank's The Diary of a Young Girl
"As long as this exists, this sunshine and this cloudless sky, and as long as I can enjoy it, how can I be sad?"
Anyone with a beating heart has shed tears while reading this book, and then has gone on to re-read it several times over, only to cry a little more. Anne Frank as the voice of WWII displays wisdom beyond her years as she chronicles the final few years of her life spent hiding from the Nazis.
John Boyne's The Boy in the Striped Pyjamas
"You're my best friend, Shmuel," he said. "My best friend for life."
Young friendship does not understand war. It doesn't recognize religions, and it has no regard whatsoever for the wired fences set up to divide their distinct worlds. Bruno and Shmuel's friendship works on one basic principle - when you hold another's hand in friendship, you never let it go, no matter what.
Robert James Waller's The Bridges of Madison County
"In a universe of ambiguity, this kind of certainty comes only once, and never again, no matter how many lifetimes you live."
He is Robert Kincaid, a globe-trotting photographer with no strings attached. She is Francesca Johnson, an Italian-American housewife living in her Iowan farmhouse. Fate brings them together for four magical days, beyond which they live their separate lives, privately pining for each other. They reunite in death, with both wishing to be cremated, and their ashes thrown off Roseman Bridge - the place where they first realized they were in love.
J.K. Rowling's Harry Potter and the Deathly Hallows
"From the tip of his wand burst the silver doe. She landed on the office floor, bounded once across the office, and soared out of the window. Dumbledore watched her fly away, and as her silvery glow faded he turned back to Snape, and his eyes were full of tears. "After all this time?"
"Always," said Snape."
The final installment of the Harry Potter series finds a place in this list for several reasons. First, there were tears of joy that it all ended well for the wizarding world and us muggles too. Second, it was the fact that each and every character's story culminated perfectly, giving the most perfect ending to a perfect adventure.

And the third, and a personal favorite reason was Severus Snape's eternal love for Lily Evans - solely because,"If there is one thing Voldemort cannot understand, it is love."
Stephen King's The Green Mile
"We each owe a death, there are no exceptions, but sometimes, oh God, the Green Mile is so long."
Stephen King's ability to stir the conscience into taking a moral stand is remarkable. To have an innocent man's blood on one's hands weighs heavily on the conscience, and keeps gnawing at the soul for eternity. The Green Mile's innocent convict John Coffey embraces death like an old friend, and in the process, frees prison guard Paul Edgecomb of the guilt of having played a part in his ending.
Wilson Rawls' Where the Red Fern Grows
"I buried Little Ann by the side of Old Dan. I knew that was where she wanted to be. I also buried a part of my life along with my dog."
There's something special about the bond that humans share with their pets. Unspoken, sublime, and intensely private, it binds them together for a lifetime, and beyond. But, like every other emotion, you don't feel it until you've felt it. Those who've lost their hearts to a pet will know what I'm talking about. The rest will have to just read this book to find out.
Erich Segal's Love Story
"What can you say about a twenty-five-year-old girl who died?"
Probably the most widely-read romantic tragedy, Erich Segal's novel is the story of Jenny and Oliver. Jenny, a grounded, working-class girl and Oliver, a loaded jock, find love in the most unusual of circumstances, only to have it abruptly culminate in the most harshest of ways.
Bernhard Schlink's The Reader
"Sometimes the memory of happiness cannot stay true because it ended unhappily."
A story revolving around the Holocaust, The Reader deals with several complexities, and haunts you even after you've put it down. Central character Hanna, remains a conundrum; do we take her illiteracy as a metaphor, or is she deviously brutal? Finally, the heart goes out to Michael, as a character who belonged to the generation of Germans who grappled with the reality of their history.
A Few More Tear-Jerkers...
  • The Notebook by Nicholas Sparks
  • The Hunchback of Notre-Dame by Victor Hugo
  • The Phantom of the Opera by Gaston Leroux
  • The Time Traveler's Wife by Audrey Niffenegger
  • My Sister's Keeper by Jodi Picoult
  • A Child Called "It" by Dave Pelzer
  • Memoirs of a Geisha by Arthur Golden
  • Veronika Decides to Die by Paulo Coelho
  • The Kite Runner by Khaled Hosseini
  • The Fault in Our Stars by John Green
Stories told in books elicit all kinds of emotions in us - they make us a part of their journey, and we willingly partake in their happiness and sorrows as we go along. And despite the sadness, we find ourselves reaching out to books like these whenever we're searching for a friend that we can call truly ours.