The 7 fictional guys I’d date in real life

When the dating world gets tough, I find myself wishing that I could go out to dinner with one of these literary companions instead.

Lauren Naefe | Stocksy United

Ever since I can remember, I’ve been a reader. It started with my mother reading tales of adventure and continued as I began to read on my own. My books became some of my favorite companions. I loved to solve a case along with Nancy Drew and I remember feeling bereft at the end of the Boxcar Children series.

Books not only taught me about adventure, they also taught me about love. Fictional boys met fictional girls and lived happily ever after. I looked forward to the day that it would happen to me in real life.

MORE TO READ: The health benefits of reading one chapter a day

When the dating scene gets demoralizing—as it often does in the non-fiction world of dating apps and blind dates—I think of my favorite male characters. I often wish that they would step off the page so that we could go get coffee or dinner together. Here are a few of my favorite fictional boyfriends to conjure from the page. Tell me some of yours in the comments!


from Calvin and Hobbes by Bill Watterson.

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This might seem an odd choice, on the surface, but I’ve done the math and realized that if Calvin was six years old when I was a kid, he’d be just the right age for me about now. His antics are a little crazy to be sure, but who doesn’t have a few of those stories from childhood? Maybe I could tell him about the time I sold Concord grapes door to door in my neighborhood without telling my parents. I’m sure he’d get a laugh out of that. Although Calvin was wild, he was also extremely smart. I’d bet that he grew up to be a professor, or a politician, maybe a scientist. Plus, his childhood crush was his bookish, outgoing and kind neighbor, Susie Derkins, showing me that he admires strong independent women. (In fact, Calvin’s mom was also a force to be reckoned with. I’d love to find a cool mother-in-law like her.) So if, for whatever reason, Susie is no longer in Calvin’s adult life, I think I could become the next bookish gal he falls for.

Datability: An intellectual fun-loving maverick, who would remind me to slow down, have fun, be curious, and nurture the child inside. But would he settle down?

Henry Tilney

from Jane Austen’s Northanger Abbey.

No list of this sort would be complete (for me) without a Jane Austen hero. I go back and forth on this often (which seems like a better use of my time than some of the dates I’ve been on). Although I love Mr. Darcy, he’s a bit prickly for my taste. George Knightley is wonderful, but he can be a little judgy. But Henry Tilney? He’s a delight. And dependable. (A quality I sometimes wish you could swipe for on dating apps.)

Henry always does what he says he’s going to do. He teases the heroine of Northanger Abbey, but he’s consistent about expressing his interest in her. He’s sweet. He seems sane and reasonable (which is hard to find). His only flaw seems to be in having a rather snobby father and in encouraging flights of fancy that led Catherine to believe that she was living in a Gothic novel. I’d definitely like to give him a few tips on decorating his parsonage.

Datability: Steady and dependable, he’s the type of man who would actually call when he says he will. And someone charming to take home to your parents.

Luke Brandon

from Sophie Kinsella’s Shopaholic books.

All throughout the series Rebecca, the Shopaholic, gets into trouble. It’s the sort of trouble that I can’t even imagine getting into, thousands of dollars worth of debt, crazy schemes of epic proportions that explode in her (and everyone else’s) face. Every time, I waited for Luke Brandon, her love interest to say: “That’s it, I’m done. This time, you’ve gone too far.”

But he doesn’t. He is patient and he helps her figure out the messes that she’s gotten herself into. I’m no Rebecca, but I love the idea of someone who isn’t afraid of a snag here and there, and will still love me even when I’m not at my very best. Part of being a soul mate is loving another person, flaws and all. (Plus, navigating money problems in a relationship is one of the big things couples need to know how to work together on.) As if that’s not enough, Luke is driven, successful, and quite the world traveler. Being around someone who is excited to explore and motivated to move mountains would inspire me to push myself to be the best I could be, too.

Datability: Loves you at your worst and best, is always honest, never late, and he would know the best restaurants for our dinner dates.

Gilbert Blythe

from the Anne of Green Gables series by L.M. Montgomery

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When I first read about Gilbert Blythe (and watched him in the movies), I wasn’t terribly impressed. He was a little boring, not terribly exciting. I understood why Anne didn’t pay too much attention to him. But as I’ve gotten older, I’m understanding more and more why she ended up with him. For one thing, he’s incredibly smart. He’s very driven toward his goals in school and eventually becomes a doctor. Beyond that, how many people will remain loyal to a childhood love through many years, with no encouragement? He tries to move on, but he just can’t shake Anne. He’s too deeply in love. When he finds his soul mate, he’s done. That’s the sort of guy I’d like to have in my corner.

Datability: Steadfast and determined, he’d never flake out on a date, and would have no problem commiting to being a boyfriend (or husband).

W.W. Hale the 5th

from Ally Carter’s Heist Society books.

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The Heist Society series, written for teens, is centered on a young woman named Kat born into a family of thieves. She’s trying to “get out of the business” but she ends up coming out of retirement for good causes. One of her friends (and potential love interests) is a mysterious young man she calls Hale. Although they’ve known each other forever, he won’t tell her his first name (but she keeps guessing). He’s very rich, and he’s a good thief, but mostly he’s looking for belonging. And that’s part of why we date in the first place: we’re looking for someone to belong to: a partner in crime, if you will.

His parents are uninvolved with his life (that makes the whole “Should we spend Thanksgiving/Christmas at your family’s place or mine?” conversation easy), and he likes being part of Kat’s family. He is protective and loyal and just a wee bit dangerous, which would probably keep things interesting.

Datability: Mysterious, dangerous and a little needy … alarm bells! But he’d definitely make for some good first-date story fodder.

Lord Peter Wimsey

from Dorothy L. Sayer’s Lord Peter Wimsey mysteries.

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First off, he’s brilliant, but he isn’t showy about it. He’s just as fond of making a joke or singing a silly song as solving a murder, but his mind is always working. He’s a collector of fine wine and rare books (both of which I enjoy) and is known to be a wonderful dancer. He has all manner of interesting friends. Like Gilbert from Anne of Green Gables, he knows how to be persistent, waiting a long time for the lovely Harriet Vane with no encouragement. (Sometimes a gal needs to see that kind of dedication in action to realize that a man is going to stick around through thick and thin.) My only hesitation is the way that crime seems to follow him so closely.

Datability: A cultured mannerly man of intellect who won’t step on your toes, but always pulls out your chair for you.

George Weasley

from the Harry Potter series by J.K. Rowling

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When I read Harry Potter for the first time, I loved the twins. They are silly and sassy, always coming up with some new prank to play. Of all of the families in the Harry Potter world, I think I like the Weasley’s the best. They are kind and loving to each other, and they take Harry and Hermione in without a thought. I imagine that now, with his twin gone, George is a bit more serious, a bit more focused on what matters, but I’m sure he still has that sparkle in his eye.

Datability: Fun-loving, kind and caring. A sense of humor in the modern dating world is a must.

What fictional character would you date? Tell us in the comments!

Cara Strickland
Cara Strickland

Cara Strickland is a freelance writer living in the Pacific Northwest. She writes about food, faith, singleness, and relationships for a variety of publications in print and online. You can find more of her work at

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