Four Literary Types You Shouldn’t Date…

Holden Caulfield might sound dreamy on paper, but in reality? Not so much. Here, one author explains the character flaws that make some of literature's most romanticized bad boys such terrible partners.

By Maura Kelly

f the beloved French writer Marcel Proust was right, it's impossible to read a novel without seeing the traits of the person you love in the main character. But maybe it also works the other way around. When we fall for a novel, after all, don't half the people we meet in real life (or at least 10 percent of them) begin to resemble the heartthrob at
We'd be lucky to find relationships as happy as any of those in real life.
its center? Think of Pride and Prejudice, for instance: When Elizabeth Bennet begins to understand that Mr. Darcy isn't the priggish rich guy she thought he was — but instead, a chivalrous man with deep loyalties and affections — we start looking for our own Mr. Darcy (or Elizabeth, as the case may be). When tempestuous Mr. Rochester and sensitive Jane Eyre realize they're soul mates, we decide we'll settle for nothing less than a connection as intense as theirs. Or we finish reading David Copperfield, and think it's probably best if we end up like Dickens' hero did — with someone who has loved us since childhood.

We'd be lucky to find relationships as happy as any of those in real life, but some other novels can get readers to romanticize bad boys. As appealing as certain characters might seem on the page, if we actually got mixed up with them, we'd surely find ourselves wishing they'd never stepped into our lives from between the covers.

Who are the (literary) types we should avoid in our personal lives? I've just co-written the new book, Much Ado About Loving: What Our Favorite Novels Can Teach You About Date Expectations, Not So-Great Gatsbys, and Love in the Time of Internet Personals, so that's a question I can answer!

Literary Bad Boy #1: Holden Caulfield, the impossible innocent
The Catcher in the Rye will always have a special place in my heart — and you can't love the book without loving its narrator, Holden Caulfield. The original disaffected youth himself, Holden is hard not to love, if you ask me. Sure, he's always griping about phonies, but isn't it endearing? And remember how he responded when his crush, Jane Gallagher, started crying over their checkers game? As Caulfield himself puts it, "I went over… so that I could sit down next to her — I practically sat down in her lap, as a matter of fact. Then she really started to cry, and the next thing I knew, I was kissing her all over — anywhere — her eyes, her nose, her forehead, her eyebrows and all, her ears — her whole face except her mouth and all." But Caulfield is so cynically idealistic that he'd be difficult to date; his love would easily turn to hate if you did the least little thing that didn't jibe with his idea of who you are (and should be).

Literary Bad Boy #2: Alexander Portnoy, the unhappy sex addict
Another book I love, Portnoy's Complaint by Philip Roth, features another male narrator, Alexander Portnoy — who appears to be a total catch. A principled and very successful lawyer for the New York City Commission on Human Opportunity, he's exactly the kind of guy your mother would want you
Caulfield is so cynically idealistic that he'd be difficult to date.
to marry. He works for the mayor of the most important city in the world; he's brilliant and hilariously funny; women find him impossibly sexy. So what's not to love? Well, Portnoy has some seriously conflicted feelings about his own mother, which have helped make him impossibly hung up about sex. That's not to say he's abstinent — oh, no; he gets more of his fair share of action from the ladies. But he can never enjoy it, because he's always too tortured by guilt. As Portnoy's therapist puts it: "As a consequence of the patient's 'morality' … neither fantasy nor act issues in genuine sexual gratification, but rather in overriding feelings of shame and the dread of retribution, particularly in the form of castration." If you happen to encounter a Portnoy — who may be recognizable because, um, he asks you to join him in a ménage a trois eventually — keep your distance.

Literary Bad Boy #3: The Reverend Casaubon, self-important brainiac
Dorothea Brooke, the heroine of Middlemarch, marries the haughty and much older Reverend Edward Casaubon — not because she loves the very unpleasant clergyman, but because she admires his intellect. Casaubon is determined to write an important work of scholarship, and he neglects everything else (including his lovely young wife) to work on his book. What ends up happening to the couple, you ask? Casaubon never achieves his goal — and Dorothea has to live with her choice to be in a miserable marriage until he dies. So if you meet a man with a messianic mission of his own, don't be too dazzled by his big plans to leave behind a magnum opus that will change the world. There's no need to sacrifice your own happiness for someone else's arrogant dreams.

Literary Bad Boy #4: Philip Carey, the restless wanderer
W. Somerset Maugham's celebrated novel Of Human Bondage is about a young man, Philip Carey, who just doesn't feel happy in any job he takes. Of course, the poor guy is orphaned at age nine and raised by a jerk of an uncle and an idiot of an aunt; his rocky childhood might help explain why it's so difficult for him to settle down into a life that will satisfy and sustain him long-term. But wow, does the guy have trouble getting his act together! After deciding that he could never become a clergyman the way his uncle would like him to, Carey is pushed into working as an accountant's apprentice. He feels so ill-suited to the work that he moves to Paris in the hopes of becoming an artist. After realizing he hasn't got much artistic talent, Carey returns home to England to study medicine, where it takes him a long time to complete his education. When he finally does, he declines to take the comfortable job that's offered to him because he wants to pursue his romantic dreams of traveling the world. Though the novel ends happily, dating an actual Philip Carey would make most women miserable. Just as he struggled to find an enjoyable career, he also had trouble being content with any of the women in his life. So, ladies: Let the wanderers wander on without you getting in the way.

Maura Kelly is a personal essay writer and author of Much Ado About Loving: What Our Favorite Novels Can Teach You About Date Expectations, Not-So-Great-Gatsbys and Love in the Time of Internet Personals. Find out more about her at
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