We’re tournament people, my husband and I. The way some people climb rocks or brew beer (I don’t know: What do other people do?), we draw sloppy 64-berth brackets in coffee-stained spiral-bound notebooks then set to vigorous, regimented discussion, rationally whittling down the field until an undisputed champion emerges. Notable competitions past include Most Intriguing City (Helsinki def. Buenos Aires) and Favorite Animal (Polar Bear def. House Cat). Most times, Matt is the tournament master, the committee of one who conceives and presents the field to me, which I then imperiously adjudicate, usually while reclining on a couch or airplane seat and eating something packed with butterfat. It’s a good arrangement, because he is a historian who likes categories and I am a writer who likes making things up.

For tournament people, the next bracket is always a gift. Matt’s mom visited last month, and she brought with her a 32-person field of literary characters for each of us to complete. Our champions were to be not the greatest or most iconic or most influential figures, but the characters we’d most like to have as friends.

“Would you want to be friends with Humbert Humbert?” Claire Messud had recently demanded of Publishers Weekly.

She had a point. We took Alexander Portnoy instead.

Serious readers know we shouldn’t go looking for friends in fiction. Better to look for moral questions, social truths, emotional possibilities—the stuff of life. And yet, isn’t it sort of fun to imagine playing Eschaton with Michael Pemulis or cruising Mexico with the Savage Detectives? Isn’t imagining ourselves among fictional people actually pretty central to the experience of reading? Literary characters certainly know this. They read and imagine, just like us. Per Holden Caulfield: “I wouldn’t want to call Somerset Maugham up. I don’t know, he just isn’t the kind of guy I’d want to call up, that’s all. I’d rather call old Thomas Hardy up. I like that Eustacia Vye.”

The truth is, most of us like or dislike the characters we encounter in books, whether we ought to or not. It’s all part of fiction’s fantasy that we get to pal around with a charming drug dealer or a righteous butler or an angry socialite we’d otherwise never get to know. Every time we read a good novel, we are essentially befriending a new incorrigible person—which makes sense, really, because most of us love incorrigible people all throughout our lives.

Still, it’s probably no surprise that the first round of our tournament was tough on sociopaths and criminals, characters who, for all their life force and complexity, we’d generally want to avoid at a party. Heathcliff would turn his dogs on us and laugh. Humbert would despise our American vulgarity even if he didn’t commit statutory rape. Jay Gatsby’s parties are intimate, but let’s face it, he only has one real friend. On the whole, the intelligent, passionate women looked better to us—Middlemarch’s Dorothea Brooke, that old Eustacia Vye—as did heroic kids like Pip and Huck Finn.

Things got more interesting as the competition progressed. Matt consistently chose female friends, while I had a soft spot for men. We found ourselves drawn not to brooders or generous hearts or agreeable conversationalists, but to characters who could, for one night at least, show us a hell of a time. Seductive charmers fared better than idealists or moral compasses; disaster flirts held our attractions longer than those who plunged into oncoming trains.

Whether our choices are likeable or not is of course purely a matter of taste: other readers might prefer a selfless governess like Jane Eyre or a judicious father like Atticus Finch. Good for them. Tournaments are by their nature catalogues of individual prejudices and preferences: what we admire, what we desire, and, just as often, what we disdain.

For us, the best literary friends skated the edge between adventure and safety: smart and interesting, but also fun. Thus did many of the greatest inner lives falter against lighter-weight opponents. Hamlet, Mrs. Dalloway, Anna Karenina: all of them among our all-time favorites, none in the final four. In each case, we felt, we’d experienced the best of them already. They’d never be better than they were in the books.  

The saddest part of any tournament is choosing a champion. For a while in the middle rounds, you get to hoard dozens of desirable specimens, revel in their variety, pretend they all belong to you. But bracketology, like eating a bag of gummy bears, requires ruthlessness, the snuffing out of many a desirable flavor, until you are left with just the one. One friend to rule them all.

In the end, Matt was forced to choose between Elizabeth Bennett and Daniel Deronda’s Gwendolen Harleth, two fine nineteenth-century females. After some vacillating and a heroic effort to put Keira Knightley out of mind, he went with Gwendolen and a spirited game of roulette.

For my part, I was left with two outsiders, and I opted for Jake Barnes from The Sun Also Risesover cool girl Ellen Olenska, the society-flouting countess in The Age of Innocencewho captures Newland Archer’s heart. Yes, Jake is impotent, but we’re not talking about sex here, we’re talking about a night on the town. And with Jake, the town would be in France or Spain and the night would last until sunrise and there’d be riotous dancing and too much drinking with all sorts of outrageous people.

“Listen,” Bill Gorton tells Jake. “You’re a hell of a good guy, and I’m fonder of you than anybody on earth.” In a novel packed with careless, aloof, and ironic exchanges, this is an earnest claim from a true friend, as good a recommendation as any.

Or, as Lady Brett Ashley puts it, “I always joke people and I haven’t a friend in the world. Except Jake here.”

It’s pretty to think so, anyway. For the sake of the tournament, I must.

Katherine Hill’s first novel, The Violet Hour, is out this month from Scribner.