Tween Books to Heal a First Broken Heart

by Jake Gerhardt

There’s nothing worse than having your heart broken. Except when it happens for the very first time.

“How many thousands of smiles had been aimed at me? So why did this one feel like the first?” Leo asks in Jerry Spinelli’s Stargirl. What a perfect expression of that feeling of first falling in love, especially that moment when you really see someone in a different light. It might be the moment you notice the way sun reflects off someone’s eyes. Or the moment you observe a simple act of kindness (like warning someone he’s about to sit a on a thumbtack, for example). Whatever it is that inspires it and whenever it happens, falling in love is an all-consuming and unstoppable force.

Eighth-graders Duke, Chollie, and Sam are faced with first-crush troubles in my book, Me and Miranda Mullaly; each guy is determined to make Miranda his girlfriend. But this is not a how-to book. Nor it is a how-to-not book (though they try many things you should not attempt). I think of it more as a guide for traveling through first love — and perhaps a broken heart. More than anything, I hope it’s a fun read.

I’ve rounded up a list of some of my favorite books on the subject. I’m a true optimist at heart and, despite bumps along the way, all the characters in these books land safely after venturing through the jungle of first love. I’m happy for them all.

  • Books tweens should read to heal a broken heart

  • What I like best about these four books is that in all of them our heroes jump back in the saddle every time they are thrown for a loss. Of course, they start out feeling sorry for themselves, they feel down in the dumps, and they worry how their peers perceive them. Despite their troubles, they refuse to give up on themselves. And in the end, they all learn a lot and are the better for it.

  • The Summer I Turned Pretty

    by Jenny Han

    Belly spends every summer at the beach with her mom, her mom’s best friend, Susannah, and Susannah’s sons, Conrad and Jeremiah. But this summer is different. Conrad and Jeremiah really see Belly as more than a kid for the first time. And she surely notices the brothers as well.

    This is a perfect antidote for heartbreak because through Belly’s eyes we see that teenage girls are just as confused as boys when it comes to romance. No one has it completely figured out.

  • The Cat Ate My Gymsuit

    by Paula Danziger

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    Thirteen-year-old Marcy Lewis is smart, kind, vulnerable, and working through some serious problems at home and school. She worries constantly about her weight and has very low self-esteem. When she meets and falls for Joel, she has no choice but to face her self-doubts. This is a great book for readers who feel like they’re going through turbulent times alone. Paula Danziger’s novels are filled with humor and joy alongside gloomy angst — just like life.

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  • Flipped

    by Wendelin van Draanen

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    Juli first “flips” for her neighbor and classmate, Bryce, in the second grade. But to Bryce, Juli is nothing but a big pain in the neck.

    It’s in middle school when Bryce begins to notice Juli. When Juli tries to save a neighborhood tree, he’s intrigued. And when Bryce’s grandfather strikes up a friendship with Juli, Bryce becomes more interested. A series of harmless misunderstandings leads Juli to question who Bryce really is and whether or not she really likes him. By this point, Bryce is very, very interested in Juli. He’s in love. But is it too late?

    No one will read Flipped and think falling in love is easy. But oh, what fun.

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  • Stargirl

    by Jerry Spinelli

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    Stargirl doesn’t play by the senseless unwritten rules that every student abides by. She’s different and is very happy that way. Leo can’t take his eyes off her and he can’t get her out of his mind. Before he knows it, they’re a couple and he’s really seeing and experiencing the world for the first time. But when Leo is forced to choose between Stargirl’s zaniness and the conformity of Mica High, he makes a fateful choice. The final scene at the school prom will stay with you for a long time.

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  • Books parents should read

  • Because it’s never too late for a refresher course on first broken hearts.

  • Wanda Hickey’s Night of Golden Memories: And Other Disasters

    by Jean Shepherd

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    Among other themes, Wanda Hickey’s Night of Golden Memories captures the anticipation and build-up to the biggest moment in a young person’s romantic life: the first date. When young Jean falls head over heels for Daphne Bigelow, he works up the guts to ask her to a movie at The Orpheum and a bite to eat at the Red Rooster. Jean’s big night is, of course, an unadulterated disaster. But his failed romance with Daphne doesn’t keep young Jean down for long. By the end of the week he has moved on to Wanda Hickey, this time planning for the night of his life at the big spring dance. Ever the optimist through his courting disasters, Jean always sees the light at the end of the tunnel.

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  • “The A&P”

    by John Updike

    Sammy, a teenage clerk at the supermarket, is mesmerized by a group of teenage girls who walk in. When the manager of the store kicks the girls out for wearing bathing suits, Sammy watches the girls leave and decides to do something rash. He tosses his apron at the manager and quits on the spot, hoping the girls hear him. Searching the parking lot, he can’t find the girls. They’re gone. Sammy looks back into the store, sees the manager working the cash register, and feels his stomach fall as he “felt how hard the world was going to be to me hereafter.”

    I’ve always liked this short story because it completely nails the rashness and absurdity of being a teenager in the presence of great beauty.