8 Undateable Male Characters

We know that quite often the fantasy is better than the reality in most things. When it comes to stories, the ones that enthrall me follow characters that I could read about constantly, but would not necessarily want in my life. Some characters skip over intriguing and exciting and fall right into the category of "absolutely not" for dating material. A real life version of any of them would be a waking nightmare!

If you have read any of the books on this list, you can probably tell from the character's name alone why I would never consider them a romantic match. If you haven't, allow me to explain.


1. Dorian Gray — 'The Picture of Dorian Gray' by Oscar Wilde

Dorian Gray is vain, thoughtless, fickle, and wildly hedonistic. He drives a woman to suicide and murders a man! He has difficulty taking responsibility for his own choices. Dorian may be super attractive, but that's never enough. Sometimes, that's the problem. If a man's face is too handsome, I'll get tired of looking at it. I'm not saying I'd prefer the face of his frightening portrait, but perhaps you can understand my point. 

Buy The Picture of Dorian Gray (Dover Thrift Editions) from Amazon.com

 
2. The Playwright — 'The Playwright' by Eddie Campbell & Daren White

The thing that makes the unnamed playwright in this comic undateable is that he reminds me too much of myself, or what I could become. His plays are well-received by the public, but he is an outsider. His inaction is the least appealing part about him. After a while, the brooding artist becomes less mysterious and more of a bore. A future with the playwright consists of weekends spent in, self-inflicted torment, and many furrowed brows.

Buy The Playwright from Amazon.com

 

3. Nathaniel P. — 'The Love Affairs of Nathaniel P.' by Adelle Waldman

Nathaniel P. teeters between typical fellow and jackass throughout The Love Affairs of Nathaniel P. He kind of cares about people, cares about his goals, but not so strongly that he is sympathetic. He does not rise to his potential, so I would not expect him to rise to a romantic partner of equal or superior intelligence. What I see in Nathaniel P. is calculated mediocrity in matters of the heart. Not attractive!

Buy The Love Affairs of Nathaniel P.: A Novel from Amazon.com

 

4. Hamlet — 'Hamlet' by William Shakespeare

Indecisiveness is death to libido, especially when it leads to tragedy, death, and mayhem. Hamlet doesn't have a sense of who he is, or if he even wants "to be." He also drops one of the most famous disses of all time on Ophelia, the woman he supposedly loves. I would not want to suffer her fate. I'm decidedly staying away from the Prince of Denmark.

Buy Hamlet ( Folger Library Shakespeare) from Amazon.com

 

5. Henry Chinaski — Various Bukowski Novels

Oh, Bukowski, your alter ego is a terror, but I can't look away. Henry Chinaski is constantly drunk and having mostly awkward sexual encounters with woman after woman, all while achieving a little literary success. He's the perfect anti-hero, and also the perfect anti-boyfriend. I've kept up with his antics, but would definitely keep my distance from the character himself.

Buy post office: A Novel from Amazon.com

 

6. Patrick Bateman — 'American Psycho' by Bret Easton Ellis

As a rule, I don't date serial killers. Even if the crimes were all in his mind, Bateman is still insane. Not to mention his general lifestyle: an investment banker who dabbles in cocaine, clubbing, and boring conversation. Again, I don't care how attractive he is. I'm not into it. Moving on.

Buy American Psycho from Amazon.com

 

7. Yunior — 'This is How You Lose Her' by Junot Diaz

Yunior seems to make the same mistakes again and again. Though written well, I grew tired of his antics throughout This Is How You Lose Her very quickly. In the short story "The Cheater's Guide to Love," Yunior's girlfriend finds out he's cheated on her with fifty women! Fifty! That's all I have to say about that.

Buy This Is How You Lose Her from Amazon.com

 

8. Ignatius J. Reilly — 'A Confederacy of Dunces' by John Kennedy Toole

Ignatius J. Reilly is my ultimate undateable character. He is so entertaining on the page, but it is completely terrifying to think of dating him. I imagine he would smell like hot dogs and ripe B.O. incessantly. He still lives at home but doesn't respect his mother, can't keep a job, and loves to argue. His fashion sense is lacking, and I doubt he would be willing to take any of my kind advice on that matter. Ignatius is perfect reality show material, but keep him away from me.

Buy A Confederacy of Dunces from Amazon.com


Even though these bachelors are not-so-eligible, their stories are all eligible for reading.

Take a trip down the undateable male character rabbit hole! Which one is your favorite?

Christine J. Schmidt

Column by Christine J. Schmidt

Christine J. Schmidt is a writer originally from New Jersey. After receiving her BFA in Dramatic Writing from SUNY Purchase, she worked at Seattle Repertory Theatre as their artistic literary intern. She recently left Brooklyn, where she was a bookseller and events host at WORD, to reside in Los Angeles. She has previously written for New York Theatre Review, and her plays have been read and produced at theaters in New Jersey, New York, Connecticut, Pennsylvania, Georgia, and Washington. Coffee is her favorite thing.

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