The Boys We Learned to Love

Who were the boy characters who formed our impressions of who guys were supposed to be, who set crushable standards, who we wanted to grow up and some day meet—or become—ourselves? 

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Y.A. for Grownups is a weekly series in which we talk about Y.A. literature—from the now nostalgia-infused stories we devoured as kids to more contemporary tomes being read by young people today.

We've looked back at some of our favorite girl characters from the books we used to read as kids. But who were our favorite boys*? Who, especially, were the boy characters who formed our early impressions of what men were supposed to be, who set crushable as well as aspirational standards? Before there was Team Peeta or Team Gale, there were characters like Gilbert Blythe of the Anne and Green Gables series, Milo of The Phantom Tollbooth, and Meg Murry's dependable friend, Calvin O'Keefe, from Madeleine L'Engle's Time Quintet. These were the boys we wanted to grow up and meet, or, maybe, be a little more like ourselves.

Gilbert Blythe. The swoonworthy Blythe (see above; L.M. Montgomery writes him as a "tall boy, with curly brown hair, roguish hazel eyes, and a mouth twisted into a teasing smile") starts things off on the wrong foot with feisty Anne after calling her her most hated of nicknames, "Carrots." But how was he to know? She cracks him on the head with a slate; he apologizes for teasing her and then spends much of the rest of the series trying to make it up to her and get her to speak to him again. In the process of that, he becomes her most important competition and motivation to succeed. Gilbert and Anne are, it turns out, kindred spirits; it's not a spoiler, we all know they eventually marry and have a family, but their romantic tension and the push-pull of the nascent love they feel for each other—beautifully imagined as a crack across the head by Montgomery—was a formative part of our early experience with crushes and relationships. Even though Anne despises him vehemently for the longest of times, Gilbert is polite, courageous, and kind, even saving her from a near drowning, though she scorns him and then immediately regrets her haste ("her heart gave a quick, queer little beat"). By the time she's ready to forgive, it almost seems he's moved on. Fortunately for us, and her, he hasn't.

The Roald Dahl boys. James (of the Giant Peach), Danny, the Champion of the World, Charlie (of the Chocolate Factory)...these were all boy heroes we likely had significant crushes on. Each of them end up in unimaginable, fantastic situations we could only dream (or read) of. Each has courage beyond his years; each gets out of a bad situation on the strength of not only his wits but also his good heart. And each is rewarded for it. Plus, James ends up with some awesome Central Park real estate.

Encyclopedia Brown. A viable male counterpart to Harriet the Spy, Leroy Brown, 10, was smart and quick-witted enough to solve crimes that left adults—including his police chief dad—clueless. Plus, he's business-minded, forming his own detective agency. And he had that mop of brown hair and his own pre-hipster flair. How can you not adore "a complete library walking around in sneakers"? (See also: The Great Brain.)

Calvin O'Keefe. In A Wrinkle in Time, Calvin tells Meg, who's plagued with self-doubt, that she has "dreamboat eyes." Then he sticks with her through whatever danger comes, and there are many. Comforting, loyal, popular (and sporty!) Calvin, a guy not afraid to hold hands. Should we ever meet such a fellow, we'd be sure to snap him up before you could say "tesseract."

Billy Coleman. Before Must Love Dogs, there was the far better and more emotionally moving portrayal of Billy Coleman in Where the Red Fern Growsone of the quintessential cry-your-eyes-out tomes of our youth. Little Ann, Old Dan, and Billy might also be the first (and best) "love triangle" we ever experienced.

Jesse Aarons. Bridge to Terabithia's main boy character became best friends with a girl, a strange "rich" neighbor girl with the funny name of Leslie, who doesn't even have a TV and is better than him at the one thing he hopes to excel at, running. In befriending her, he gets over his own prejudices and those of the kids at his school. That, and the fantasy world he creates with Leslie, is enough to love him for. But then something truly awful happens, and the man he'll grow up to become really emerges. What happens to Leslie breaks our hearts (again and again: Do not read this book if you don't want to break down in hysterical tears), but Jess helps heal the heartbreak as much as he can.

Max. The main character of Where the Wild Things Are might grow up to be a holy terror in a wolf suit, the bad boy that you know you shouldn't date but are compelled to, anyway. While you won't end up with him, he's fun, fun, fun, and never boring. There's something to be said for that.

Milo. Cool name, cooler kid. Milo of The Phantom Tollbooth is bored because life is, well, boring (we get you, Milo). When he receives the mysterious gift of a miniature tollbooth complete with a map of what lies beyond, his boredom inspires him to drive through his new tollbooth in his toy car. He is transported to an entirely new magical land, where totally not boring things ensue. Milo taught us that being bored is a waste of time, because there are adventures to be had everywhere. Also, he saves princesses, and he can drive.

Henry Huggins. Another boy who loved dogs (aw, Ribsy), Huggins came before Beverly Cleary's Ramona series, which ended up surpassing the Huggins books in popularity. But it's not like Henry was a schlub, though he was sort of the "every boy." He held down a newspaper route, had an awesome dog that he nurses to health after he finds it as a stray, and has been dubbed "The modern Tom Sawyer" or, by us, "the lothario of Klickitat Street." Like Milo, he has wheels.

The boys of The Outsiders. This list would not be complete without the most smoldering of boys trying to become men: Two-Bit, Ponyboy, Johnny, Dally. The characters in S.E. Hinton's Y.A. book about boys growing up on the wrong side of the tracks, trying to do the right thing and become men despite the challenges they face—gangs, violence, death among their own—are rebels in slicked-back hair. Smoking their cigarettes, they were dangerous; they were sexy, too. They were the boys we wanted to date, the boys we wanted to be, especially the survivalist writer, Ponyboy. Hinton wrote the book when she was 16, meaning that she, too, was likely not entirely immune to their charms—in fact, Ponyboy was said to be based off a boyfriend she'd had.

Joe Willard. Betsy Ray and Joe Willard—the proud, aspiring, sensitive, intelligent orphan boy of the Betsy-Tacy series (of course, he's no slouch in the looks department, either)—have a kind of Gilbert Blythe and Anne Shirley thing going. He inspires her to work harder; they're competitive; jealousies spring up between them. They grow together and apart and then together and apart again, but always with that back-of-the-heart adoration for each other, even if they're dating other people. They write each other the most wonderful letters! There are misunderstandings and awkward situations and bad timings that predate and trump any old boring rom-com. You know they end up together. They have to. But how they get there is half the fun. Extra points, for the insiders among us: They're a power media couple.

*Disclaimer: We're drawing from not just the books traditionally defined as "Y.A." but more generally from the canon we grew up on as kids.

This article is from the archive of our partner The Wire.