Cry with the Sky: Tear-Jerking Books to Read on a Rainy Day

Before writing this article, I went to my Goodreads account and checked one of my shelves called “Books That Made Me Cry.” There are currently 142 books under that shelf. Full disclosure: I only list books there that made me cry extra hard for an extended period; 42 books have done that. Some people haven’t even read that many books in their life.

A bulk of those books, I’ve read when I was in my first two years in college. For some reason, I wanted—no, craved—books that would make me sob so hard I’d soak my pillow.

Now that we’re in the thick of the rainy season, I figured I’d share with you some of those books. There’s just something about the gloomy weather that makes you want to bundle up and read sad stories.

Fair warning: if you thought “The Fault in Our Stars” was sad, prepare yourself for the exquisite pain the following books will bring:

Tiger Lily by Jodi Lynn Anderson

View this post on Instagram

q o t d: What kinds of endings do you like the most ❤️? ⠀ a o t d: It depends on the book, the characters, what the author made me feel. The novel in the picture is a retelling of Peter Pan, told by Tinker Bell and featuring Tiger Lily. It’s one of the most touching book I have ever read. Delicate, moving, poignant and awfully written. I know that most of you tend to overlook whatever doesn’t fit the “Beauty and the Beast” category. But believe me if I say that this novel will haunt you for months to come. Tiger Lily will haunt you. Because you will be aware, from the very beginning, that Peter won’t choose her. And his ultimate decision will still break your heart… But that’s okay, I suppose. Some books are just perfect the way they are. Heartbreaking endings and all ❤️. ⠀ ⠀ ⠀ #tigerlily #jodilynnanderson #retellings #fantasyya #readingya #bookaesthetic #bookster #bookphotography #bibliophiles #mywhitetable #minimalstyle #prettylittlethings #mybeigelife #momentsofmine #theartofslowliving #visualoflife #lifestyleblogger #thatsdarling #darlingmoment #chasingseasons #postitfortheaesthetics #liveauthentic #thehappynow #folklife #thecreative #inspiremyinstagram #frenchstyle #frenchvibes #pursuepretty

A post shared by — Liv (@bookstolivby) on

I used to think of Peter Pan in relation to Wendy Darling, Captain Hook, and Tinker Bell. I didn’t even know who Tiger Lily was until I had to dress up as her character in 3rd year high school English class. Even then, the only thing I knew about her was that she’s a Native American princess.

When I read Jodi Lynn Anderson’s “Tiger Lily,” everything changed. Perhaps it’s because we’ve all been where she was in this book: attracted to someone or something that’s inherently bad for us. Told through Tinker Bell’s point of view, this book will make you feel the rush of falling in love for the first time and break your heart thinking about all the what-ifs between the main characters.

The Nightingale by Kristin Hannah

Kristin Hannah has written several books before she penned “The Nightingale,” an international bestseller that swept dozens of literary awards in 2015. These honors include the coveted Goodreads People’s Choice Award for Best Fiction and Book of the Year awards from Amazon, iTunes, and the Wall Street Journal.

I feel like any form of media that tackles different World War II stories has the power to make me cry. In “The Nightingale,” the story is about two sisters living in France whose lives are torn apart when the War began. This book is a beautiful kind of tearjerker because of its portrayal of women during WWII. Their contributions and sacrifices during that time are beautifully—but not romantically—portrayed in this book.

The Song of Achilles by Madeline Miller

View this post on Instagram

Hello, hello beautiful book dragons and Happy Fourth of July if you celebrate! The girls and I will be driving up to Denver so I can take them to a firework show. Do you have any plans for today? · · · · The Song of Achilles is one of those books that has been sitting on my TBR for way too long, but one I know will be a five star read once I finally get to it. · · · · What are some of your five star predictions? I loved An Enchantment of Ravens so much I'm positive Sorcery of Thorns is going to be five stars! · · · · The Song of Achilles synopsis: "Greece in the age of heroes. Patroclus, an awkward young prince, has been exiled to the court of King Peleus and his perfect son Achilles. By all rights their paths should never cross, but Achilles takes the shamed prince as his friend, and as they grow into young men skilled in the arts of war and medicine their bond blossoms into something deeper – despite the displeasure of Achilles' mother Thetis, a cruel sea goddess. But then word comes that Helen of Sparta has been kidnapped. Torn between love and fear for his friend, Patroclus journeys with Achilles to Troy, little knowing that the years that follow will test everything they hold dear. Profoundly moving and breathtakingly original, this rendering of the epic Trojan War is a dazzling feat of the imagination, a devastating love story, and an almighty battle between gods and kings, peace and glory, immortal fame and the human heart."

A post shared by Areli Lefevre | Book Dragon | (@offaerietalesandbooks) on

Almost everyone knows the story of Achilles: the greatest of the Greek warriors. A Trojan War hero. Invulnerable except for his heel, which later became his downfall. But “The Song of Achilles” is told through Patroclus’ point of view. Long portrayed by historians as Achilles’ best friend since childhood, Patroclus is depicted here as Achilles’ lover.

If you’re like me, who thought that just because she knows the fate of these two characters, she’s prepared, you’re wrong. Miller’s writing is the embodiment of “poignant.” Your tears will have no choice but to fall.

Letters to the Lost by Brigid Kemmerer

Many people look down on Young Adult genre for being too shallow. I, myself, am not fond of YA books in contemporary settings. That’s why I was a bit hesitant to read this book when my friend recommended it. But boy was I glad that I gave this a chance.

Told through Juliet and Declan’s alternating points of view, “Letters to the Lost” tackles the hardships of growing up, being judged, and the secrets that can tear families apart. There’s also a heavy dose of anger, loss, and grief — a trifecta of themes guaranteed to make even the heartless cry.

 It Ends With Us by Colleen Hoover

The first Colleen Hoover book I read was “Maybe Someday” five years ago. Since then, I’ve been a huge fan of her works because they’ve never failed to make me cry. But “It Ends With Us” hits differently.

I won’t get into the specifics because this can turn spoiler-y real fast, but Colleen Hoover’s most provocative book made me pause and think a lot of times throughout this story. It’s romance, yes, but it’s more than that. It’s the story of so many courageous women and even men. A story that doesn’t often get told because of the stigma surrounding their situation. The honest way Hoover handled this story made it even more thought-provoking and heartbreaking. Fortunately, it will reach a wider audience because Jane the Virgin‘s Justin Baldoni is turning It Ends With Us into a film.

Now you may already have an endless TBR pile. You may not even be in the mood for tearjerkers and want to read nostalgic books instead. Or perhaps you’d rather binge-watch Netflix shows . But the next time it rains or the sky’s full of dark clouds, pick up one of these books and cry the sky.

Leave a Reply

Your email address will not be published.