Nice guys don’t flirt:
How and why they should
By Jenn Shreve
When my close friend Eric developed a crush on a woman who worked in a nearby tea shop, he spent weeks contemplating how he would approach her. Striking up a conversation while ordering Earl Grey seemed too bold. If he lingered too long at a table by himself, he'd seem like a loser. But if he showed up with a group of guy pals, he might come across like a macho jerk.
He settled on arriving at the shop with a posse of female friends to demonstrate, as he puts it, that he was "pre-approved by the female sex." In this way, he was finally able to nervously introduce himself to the woman behind the counter. Amusingly enough, they became friends. She introduced him to her co-worker, whom he ended up dating for more than a year.
My boyfriend, when he was single, used to buy women drinks. But before the beverage could even be delivered, he'd run out of the bar, unsure and afraid of the next step. A handsome, eligible dentist I know recently needed several pep talks before he could phone a woman. Another nice guy pal has simply given up on flirting. He cannot imagine a line or approach that wouldn't seem contrived or insulting to a woman's intelligence. Better not to flirt at all than inadvertently confirm a woman's worst fears about male behavior.
What a dreadful loss to womankind! Nice guys — the ones we want to meet and fall in love with — don't flirt. Meanwhile, a verbose minority of jerks wreaks havoc with their uninhibited flirtatious ways. They whistle at women on the street, introduce themselves with cheesy lines, leer at breasts and legs but never brains. In short, they sully the reputations of their fellow men with rude, crude and socially unacceptable behavior.
Why don't nice guys flirt? A nice man considers the woman's feelings above his own. He figures she probably doesn't want to be disturbed by a total stranger; best to leave well enough alone. A nice man is humble. He does not consider himself to be God's greatest gift to womankind, so he does not assume that she will see him as such. A nice man puts friendship before sex. He would rather get to know somebody slowly than come on strong from Day One.
The fear of making a bad impression looms large. Men, if they want to flirt successfully, must come across as both confident and harmless. It's a difficult balance to maintain. If you lean too far in either direction, the consequences are disastrous.
"The opposite of confident is a loser,” Eric says. “The opposite of harmless is even worse."
Throughout my adult life, for reasons I can't quite explain, my close friends have almost all been men. Not just any men, mind you. These are Grade A quality chaps — nice, smart, handsome, polite — the kind you want to place atop a pedestal and bring home to mom. Thanks to these friendships, I've gotten a first-rate education in the mind of our brothers of the XY chromosome. I've come to understand their hopes and fears, their joys and guilty pleasures.
And when it comes to anxieties, few things rate higher with these fellows than flirting. They talk about it constantly. I've been asked to scour e-mails and phone messages for hidden messages. I offer the female take on when to ask a woman out and how. Hollywood would have us believe that men stand around in locker rooms and sit on barstools bragging of their latest conquests. In reality, they are probably bemoaning their paralysis when it comes to approaching, chatting with and asking out members of the opposite sex.
In hopes of helping men overcome their flirting phobia, I've written several articles on the topic. In one, I interviewed a flirting expert. For a glossy national men's magazine, I sent a romantically challenged acquaintance to get private lessons on flirting technique, then unleashed him on a series of bars and parties. I lurked in the background, furiously taking notes.
The secret to giving good flirt, I've learned, is the ability to read and react properly to the signals a woman is sending. A smile means smile back. Two smiles means find an excuse to say hello.
The reason most men fail in flirting is they don't wait for the woman to make the first move. Numerous times I've been somewhere minding my own business when out of nowhere a stranger pops up and starts trying to make conversation. He may be very nice, good-looking and charming. But in my mind I'm wondering, Why in the hell is this man talking to me? What does he want?
Men need to pick their moments well. If a woman is busy, preoccupied or stressed out, the best flirt in the world won't impress her. For ages, I've been telling my friends that if they want to meet and flirt with women, they should go in for weekly manicures.
Flirtatious conversation should focus on her, not you. Ask about her interests, her work, her friends. Find common interests and explore them. Lines never work.
If a man is flirting with someone and, for whatever reasons, she stops sending warm signals, it is important to quickly and politely withdraw. For example, "I'm meeting someone" means "Leave me alone, freakazoid," not "Please stay and talk to me until my date arrives." To accept rejection gracefully is flirting's greatest challenge. I constantly find myself reassuring friends that the reasons for a woman's lack of interest are rarely ever personal.
In the past when men have started flirting with me uninvited, I've responded with such charming tactics as: 1. Smiling and nodding while looking at anyone or anything other than him. 2. Pretending that he doesn't exist. 3. Walking away. Or, 4. Telling him in no uncertain terms to go the way of the devil.
Today, I no longer give the automatic brush-off. Instead I try to convey that I'm flattered but not interested (unless he's rude; then he automatically gets the No. 4 treatment). Because I sympathize with how difficult it must have been to make that initial gesture. And because, if the guy seems nice, I want to encourage him in his flirting endeavors. Chances are, if he keeps at it, he'll eventually introduce himself to the right woman.
Jenn Shreve writes about media, technology, relationships and popular culture for Salon.com, the San Francisco Examiner, Wired and other publications. Her last story for UnderWire was about women escaping abuse.
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