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At the end of a year, Strauss learned his lessons so well that he became one of the most successful PUAs in his strange little fraternity. He ultimately told his “Ugly Duckling to Prince Charming” tale in The Game: Penetrating the Secret Society of Pickup Artists, a 2005 memoir that became another New York Times bestseller.

Guidelines about sex, love, and romance—expressed neveristically—have also been authored by women. Some of the best have come from Cynthia Heimel, a columnist for many years at Playboy and the Village Voice. In Sex Tips for Girls (1983), her first book, Heimel provided this rule:

Never, under any circumstances, ever go to bed

with a man you’ve just met in a bar.

Or any man you hardly know. No matter what.

There is no equivocation in this advice. Earlier in the book, though, Heimel had a little fun answering the question “Should you sleep with a man on the first date?” She immediately answered, “No, you should not, no matter what.” But then, after proclaiming, “This is a hard-and-fast rule. There are no exceptions,” she concludes unexpectedly: “Unless you really want to.” Her book also contained other admonitions, some expressed in unforgettable ways:

Never ask if it’s in yet.

Never, ever talk about how good you are in bed.

Never try to establish a successful flirtation when your hair is a mess.

Never spend more than an hour and a half cleaning your apartment for a fellow.

You must never fake an orgasm.

Faking an orgasm is an act of self-degradation.

No area of life is filled with more mistakes and missteps than the world of sex, love, and romance. As a result, there are few arenas filled with more cautionary warnings, dissuasive advice, or proclamations about what one should never do. Let’s continue our look at them in the rest of the chapter.

Never confuse “I love you” with “I want to marry you.”CLEVELAND AMORY, quoting an anonymous

father’s advice to his sons

Never be rude in a bar, because the guy you snub tonight

could be your job interviewer tomorrow.DAN ANDERSON & MAGGIE BERMAN, in the 1997 book

Sex Tips for Straight Women from a Gay Man

Never date a man prettier than yourself.ELIZABETH ANDERSON

Never let the little head do the thinking for the big head.ANONYMOUS

Often described as “advice to teenage boys,” these words have been delivered by countless fathers, coaches, and other authority figures speaking frankly to hormone-driven young men. The saying has been around for many decades, but it always enjoys a resurgence of popularity when a powerful or high-status male falls from grace after an embarrassing or calamitous affair. There are a number of other anonymous neverisms in the category of sex, love, and romance. Here are some of my favorites:

Never use the word “fine” to describe how a woman looks.

Never run after a woman or a bus, because there’s one every ten minutes.

The ones after midnight are not as often, but they are faster.

Never bag on another man’s fetish.ANONYMOUS

Urbandictionary.com describes this modern “code of conduct” this way:Never bag on (make fun of, put down) someone else’s fetishes or sexual turn-ons, because lurking in the dark corners of your mind are some crazy turn-ons that you would never want anyone to find out about, and if they did, you wouldn’t want them to bag on you for it.

Never kiss by the garden gate.

Love is blind, but the neighbors ain’t.ANONYMOUS RHYME

“Never Let a Sailor Lad an Inch Above Your Knee”ANONYMOUS ENGLISH FOLK SONG

This is the title of a bawdy nineteenth-century English folk song. Why should a fair maiden heed such advice? The lyric below, from a sad-but-wiser woman, explains why:Come all of you fair maidens, a warning take by meAnd never let a sailor lad an inch above your kneeFor I trusted one and he beguiled meHe left me with a pair of twins to dangle on my knee

Never assume that the guy understands

that you and he have a relationship.DAVE BARRY, in Dave Barry’s Complete Guide to Guys (1996)

Barry called this “The Number One Tip” for women who want to have a relationship with men. With tongue in cheek, he went on to explain:The guy will not realize this on his own. You have to plant the idea in his brain by constantly making subtle references to it in your everyday conversation.

After providing several not-so-subtle examples, Barry continued:Never let up, ladies. Pound away relentlessly at this concept, and eventually it will start to penetrate the guy’s brain. Some day he might even start to think about it on his own.

Never date a man who knows more about your vagina than you do.ROBIN BARTLETT, to Meg Ryan, in the 1988 film City of Angels

This is one of my all-time favorite movie quotations, but it goes by so quickly that it’s easy to miss it. The line is delivered by Bartlett, playing a pediatric nurse named Anne, to heart surgeon Dr. Maggie Rice (played by Ryan). The distraught doctor, who has just lost a patient in surgery, escapes to the hospital nursery for some quiet time. Sitting among the newborn babies, she begins to wonder if she should have chosen another specialty. “I should’ve gone into pediatrics,” she finally confesses to Anne. Attempting to lighten the mood, the nurse introduces her vaginal dating admonition by saying, “Oh no. Every guy you meet is either married or a gyno.”

One simple rule, ladies:

Always be classy. Never be crazy.

Okay, actually it’s two simple rules,

but trust me, you will never be sad you followed them.GREG BEHRENDT & LIZ TUCILLO, on losing it after

a bad break-up, in He’s Just Not That Into You (2004)

Never date a man who wears

more jewelry—or worries more about his wardrobe—than you.LARA FLYNN BOYLE, quoting her mother

Never force anyone to do anything for you “in the name of love.”

Love is not to be bargained for.LEO BUSCAGLIA, in Loving Each Other:

The Challenge of Human Relationships (1984)

Never date a man whose belt buckle is bigger than his head.BRETT BUTLER

Butler said this in the popular 1990s sitcom Grace Under Fire, in which she played Grace Kelly, a single mom struggling to raise her three children. Kelly, a recovering alcoholic with an edgy quality, was famous for her no-nonsense remarks. She also once said: “Never take a job where the boss calls you ‘babe.’”

Never refer to any part of his body below his waist as “cute” or “little.”C. E. CRIMMINS, in The Secret World of Men:

A Girl’s-Eye View (1987)

This appeared in Crimmins’s clever satirical travel guide for women who are planning a trip to the foreign—and often extremely exotic—nation of Boyland. Crimmins’s spoof holds up very well after nearly twenty-five years. In a section on “Sex in Boyland,” she added: