Pimpin’ Ain’t Easy: How to Score like a Literary Hero/Anti-Hero

Jul 8th, 2010 | By | Category: Columns

Awww yeah, guys and girls!

Who doesn’t want to become luckier with the opposite sex (Answer: nuns)?  Listen, we all want to love and be loved (while avoiding a plethora of venereal diseases). But it’s tough out there! And many of us have, more often than not, failed in scoring our crotch’s desire.

You’ve probably been relying on self-help periodicals and recreational drugs as ways to meet your possible conquests. This has probably led you to be as successful on the battlefield of love as Civil War General Braxton Bragg (who had nothing to boast about! ZING!).

So you know what we should all do?


No wait…

…what we should do is harken back to great literary heroes/anti-heroes (just gentlemen, ladies can’t be heroes; they are too busy ironing in Ye Olde Washroom). These dudes knew how to pull, so let’s grab a chair, learn how to read, and delve into what made these guys so great with getting their horizontal hump on!

Robert Lovelace from Clarissa by Samuel Richardson

Style: Your step-father’s Benedict Arnold Halloween costume

Type: Ruthless seducer

Best Line: “If a man could not make a lady in courtship own herself please with him, it was as much and oftentimes more to his purpose to make her angry with him.”

Lovelace, master of the Neg, was such a rake, the ladies he conquered either died in childbirth or became whores. High five dudes!

The key to being like Lovelace is never taking “No” for an answer. Can I pay for dinner? No. Lets just be friends. No. Will you stop calling? No. Listen, it’s nice you’re feeling super passionate about me, but can you please not kidnap me and hold me hostage in a brothel? Hmm. No.

Lovelace is all about persistence. Never give up! It’s what makes America great. (But since Lovelace is British, persistence expires during the Revolutionary War. SERVED!)

Upside: Lovelace is the precursor to every romance novel novel bad boy.

Downside: Lovelace is the precursor to every romance novel bad boy.

"See the banked passion in my eyes? Focus on that and ignore my fists in your face. Aw yeah!"--excerpt from Clarissa by Samuel Richardson

Vicomte de Valmont from Les Liaisons dangereuses by Pierre Choderlos de Laclos

Style: Groom at a Labyrinth wedding

Type: Intelligent slut machine

Best Line: “I foresee that vengeance will move faster than love.”

Grace. Gift of gab. Heels on his shoes. Prince? The Purple One wishes . Valmont adds a stylistic edge to Lovelace’s Stockholm Syndrome Love Potion, so instead of ladies becoming whores after a love fest, they lock themselves in a nunnery or just take it on as a new vocation. That’s right, only God gets those fine specimens when Valmont is done with them!

To be a Valmont, you need cunning and a good lawyer (following up on those “Cease and Desist” letters from your future love can be a pain). You also need a really great wingman/wingwoman who can steer you toward your next sexual take-over, as well as informing you if your brocade jacket makes your butt look big. But stay clear of closeted underage hotties with helicopter mothers. You’ve been warned.

Upside: Destined to always score.

Downside: Fatal wound; brought to you by the boyfriend of a chick you banged.

"Whatever you do," Valmont purred. "Don't muss up the wig, as it is the source of all my powers." excerpt from Les Liaisons dangereuses by Pierre Choderlos de Laclos

Alex from A Clockwork Orange by Anthony Burgess

Style: High school steampunk convention

Type: Bad boy

Best Line: “Appy-polly-loggies.”

Are you into serial rape? No? Moving on…

Upside: Free will.

Downside: Beatings, the Ludvico Technique.

After we go to the milk bar, I will do delinquent things to you. Welly, welly, welly, welly, welly, welly, well.


Ethan Frome from Ethan Frome by Edith Wharton

Style: Bedraggled farmer (aka hipster)

Type: Sad sack with a heart of gold

Best Line: “I want to put my hand out and touch you. I want to do for you and care for you. I want to be there when you’re sick and when you’re lonesome.”

To be a successful Ethan Frome, you need to showcase your vulnerability, but not so much that you end up horribly crippled in a sledding accident. Suggestion: a book of poetry and some eye drops. Remember not to talk a lot, and when you do speak, make sure your speech is rough and decorated with lots of apostrophes as if it were written out phonetically.

Always stand a little away from the crowd when you are in a public area, showcasing your openness to feeling feelings and emoting emotions that the rest of the cold, cruel world cannot begin to understand. To expedite the lie that you are thoughtful, grow a beard.

Upside: The opposite sex will enjoy your sensitivity.

Downside: You might be asked to grow a pair.

Girl, you are so fine we should be related! We are? Well let's get our relations ON."--excerpt from Ethan Frome by Edith Wharton

Maximilian (Maxim) de Winter from Rebecca by Daphne du Maurier

Style: Donald Trump (with hair)

Type: Cardboard

Best Line: “Forgive me. I was very rude after lunch.”

Wow, you are handsome! And well-dressed! And moody And…well, not that much else. But the opposite sex digs your standoffish mysterious dickishness, because it obviously alludes to a personality that you actually don’t have!

The Maximilian is perfect for those just starting out with literary pimping. Test your wings and go to Saks Fifth Avenue (clearance section). Pick out some awesome duds and go out to da club. Be sure to fold your arms, furrow your brow, and focus on the wallflowers, as they tend to be more willing to overlook your lack of dialogue for handsomeness and the fact that you are the owner of property that may or may not be haunted by your unbelievably good looking ghost wife.

Upside: Always looking fly.

Downside: Dead wife ruining your groove.


V from V for Vendetta by Alan Moore

(Comics are literature. Professor Stan Lee says so.)

Style: Masquerade party on acid

Type: Badass

Best Line: “Please allow me to introduce myself… I’m a man of wealth and taste. “

To be V, you can’t be no shrinking violet. Make sure that while you’re out prowling, you impress a possible hook-up by getting into a verbal alteration with a Republican, Democrat and Libertarian, before setting the bar on fire.

Upside: Can work a cape.

Downside: Is a renowned computer hacker, but isn’t good with cell phones.

Behind this mask lies the potent elixir of pure sensuality. Oh and anarchy. I guess.

Ashley Wilkes from Gone with the Wind by Margaret Mitchell

Style: Great great grandpappy, minus the handgun and white hood

Type: Sober southern gentleman

Best Line: “I don’t love you.”

Many people pick Rhett Butler as the master hustler, but those people seem to forget that stuffed shirt Wilkes has all the right moves. Indeed, he had both Scarlett O’Hara and Melanie Hamilton wrapped around his well-manicured fingers.

Ashley Wilkes’s secret? Super politeness followed quickly by disinterest. Play hard to get! For instance: when you nicely ask your sexy interest about his/her day, be sure to wander away while they are in mid sentence. Or, offer your possible hump partner a ride home from Bible study, and then drive off without them. Remember: you’re a wild, disinterested horse that can’t be tamed!

Upside: Great table manners.

Downside: Like Ethan Frome, suffers from Doormattitude.

"Scarlett," Ashley whispered passionately. "I feel so apathetic towards you!"--excerpt from Gone with the Wind by Margaret Mitchell

Roland Deschain The Dark Tower Series by Stephen King

Style: XXXL Cowboy Costume from Party City

Type: *Stares*

Best Line: *Stares*

The fact that Clint Eastwood is inspired by this dude means you need to get this shiz on lockdown! Question 1: Are you so masculine you eat tree bark for breakfast while bench-pressing tractor-trailers? Question 2: Do you have no sense of humor, because you’re too busy fighting the good fight and jokes are for sissies? No? What, are you on your period you little bitch?

If you want to score and score big, you gotta talk the talk and walk the Ka-Tet talk. That means you need a weather-beaten duster and hands the size of overcooked hams. Remember: your past is a mystery, so if your love interest asks what you did on Sunday, just grimace and ask if he/she can help you solve a riddle. Otherwise, they are dead to you.

Upside: Manly.

Downside: Is actually allergic to roses. Shhh, don’t tell!

Underneath this manly exterior--is a more manly exterior!

Well,  sexually-charged men and women who want to get freaky, I hope this list helps you in your quest to bone. I’d like to leave you with the immortal words of ladies man Lord Byron: “Between two worlds life hovers like a star, twixt night and morn, upon the horizon’s verge–Get it girl!”


Eileen’s heart will always remain with Captain Ahab. He is so fine.

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