Flirt Like a Pro

Peter is looking to score. The scene: a warm night at the Casanova, a hip watering hole in San Francisco's Mission district. Inside, Peter saunters up and tells the bartender he'd like to buy a drink - anonymously -for a pert blond sitting with friends at a nearby table.

"Why don't you just go introduce yourself?" asks a heavyset dishwater blond, alone and brooding within earshot. Peter explains that he just wants to make a nice gesture. No strings attached. The interloper isn't having any of it. "Women like to know who's buying their drinks," she says, delicately avoiding the fact that she has no need to spend time wondering who bought hers. She has a point. For a minute or two they discuss methods of picking up women. Peter walks away.

Meanwhile, the pert blond has gathered up her things and is heading toward the door. Peter cuts her off at the entrance. "Don't leave," he says. "I want to buy you a drink."

She pauses a second. Then she looks at him and states, with heart-chilling iciness, "Whatever," before strutting out the door.

OK you're thinking, ouch. But wait. It gets worse.

Just as Peter is about to give up and head home solo, in walks the mother lode: a birthday party of drop-dead gorgeous 22 year-olds. Peter is all over them like a hacker in the CIA's mainframe. He grabs himself a party hat (first mistake) and starts chatting up a leggy, doe-eyed number named Molly. Things are progressing nicely, or so he thinks, so he offers to buy her a drink. "I'm taking care of a lot of people in my family right now," she responds. "I don't know if l can take care of anyone else." Peter buys her a drink anyway.

His reward? She mocks him to her friends as she gulps it down. It's only strike two, but Peter is out. There will be other bars, other women, other nights. On paper, this handsome, non-drug-addicted, sweet 28-year-old is a great catch. But while it would be easy to chalk his bad night on the town to run-ins with two bitches, the truth is somewhat more painful: Peter is a lousy flirt. And unless he can brush up on his flirting skills, he will face endless nights of surly women, big bar tabs and restless sleep in a perennially empty bed.

There is a fine line between expert flirt and romantic putz. Most guys brag how they're the Rico Suave of the flirting world, but in reality the facts are a little less flattering. Among my friends, rare is the occasion that a man approaches one of us and doesn't get blown off. You may massage your wounded ego by dismissing us as snobs, but that's not true. This much is: you can be the best-looking man in this hemisphere, make more money than Bill Gates, be smarter than Einstein and more sensitive than the Dalai Lama, but if you approach me with a line -1 don't care how witty, sly or funny you think it is - you're outta here without so much as a second glance.

So how does one approach a beautiful woman and not come off as an idiot? As with ballroom dancing or a perfectly choreographed flea-flicker, flirting is an art. It is learned through observation and perfected through practice. A few have the innate skills to flirt successfully without so much as a dress rehearsal, but most of us must learn to flirt before we can get results.

In the animal kingdom, each species has its own elaborate mating ritual. Birds sing. Blue-footed boobies dance. Certain kinds of snails initiate courtship by shooting darts at each other. Humans are more complicated. There is no prearranged set of behaviors that will guarantee some action. We have eye contact, hot-and-heavy e-mail exchanges and social lubricants such as alcohol. All of these playa part in that elusive art known in finer circles (albeit Edwardian finer circles) as coquetry. At the core, there are only a few basic steps.

Good flirting is a two-way street. Pickup lines fail because they're one-directional, one-dimensional bullets aimed at another person who is considered little more than prey. Artful flirting is an interaction between two people, one which elevates everyday conversation to a new level. An introduction is no longer a mere "nice to meet you": it is a playful quid pro quo between two parties interested in getting to know one another. It is an escalation-the work-related e-mail that turns into a friendly back-and-forth about the boss's outfit, then a discussion of weekend plans.

My friend Richard, 30, was recently filling his plate at a gourmet salad bar when he bumped elbows with an attractive woman to his left. "Left-handed," she said, smiling. Instead of mumbling, "Excuse me," and moving on to the arugula, Richard laughed and said, "Yeah, it's tricky being left-handed. I've knocked sushi right off of people's chopsticks. I'm dangerous." Richard has a girlfriend, so he wasn't about to take things further. But if he'd wanted to, he was off to a good flirting start: a chance everyday incident opened up into an exchange worthy of Tom Hanks and Meg Ryan. He could have chatted long enough to ask for the woman's number. And probably gotten it.

Nicole, 26, says she gets called a flirt all the time, when she's really just a good conversationalist. "When I go out I talk openly, ask people questions about themselves, let them know a little about me. It's the real conversations you take with you." The lesson for you: practice makes perfect.

Take it slow. Francesca Gentille, a coach who holds workshops on improving people's flirting skills, compares it to dancing - only with the woman in the lead. She sends a signal, perhaps a smile or eye contact. The guy responds with a gesture in kind. Then he waits for the next move. If it doesn't come, the dance is over. If she sends another signal, the dance continues. Accept one hard-to-swallow fact: almost always, women are in control in the flirt game.

That's why Peter's timeless tactic of buying a woman a drink, no matter how well intentioned, doesn't work. "He's too strong," Gentille admonishes. "By just jumping in front of women, he's invading their territory. Even for the best-looking guy, that would be threatening." Gentille goes on to add that "any woman knows she can get a guy to have sex with her any day. But she doesn't know if she could get a man to be in a relationship with her any time. To just jump in front of a woman, or to buy a woman a drink, implies, 'I'm going to get you drunk based on your looks.' "

Good flirting is never goal-oriented. If you are looking for a relationship, to get laid or merely to stuff your ego, it's going to come across in how you flirt. And there are few things less attractive than somebody who overtly sends a signal that he wants something. Like Richard's chance encounter at the salad bar, most flirting doesn't lead to anything consequential, but it should always leave both parties feeling better about themselves.

One of my best flirting memories is of a gorgeous fellow who approached me at a bar with an invitation to see his band. I asked what kind of music he played, and before long we were engrossed in conversation about music, work, life, the universe, whether Budweiser was making a comeback. I went home that night feeling attractive, smart and truly charmed by this self-assured stranger. A week later, I showed up to see his band play, only to learn from his friends that he had a girlfriend. But I wasn't upset. He'd made no promises on the night we met. We were, after all, just talking.

Of course, flirting done right can, and often does, lead to bigger and better things. At the end of a good conversation, you may want to ask someone out, or at least get a phone number. If it's clear through body language, eye contact and the tone of what's being said that both parties want to continue things, then offer your number. That way nobody's on the spot, nobody's desperate-just like good flirting itself.

Even flirting lightly with women you aren't especially interested in can be beneficial in the long run. "Women talk and they have a really strong network," Gentille points out. "I wasn't interested in my boyfriend when I met him, but he had dated several of my girlfriends and they all said he was a really nice guy." She kept that in mind, and eventually the two got together.

Play up your best qualities. Never use some crutch, like a sports car. Ask a woman about her worst flirtatious encounter and inevitably it involves a line: the bozo in American Pie who parks his car, looks at his date and says, "Suck me, beautiful," is but one recent example of what not to do. Nicole remembers a guy who, after noticing her pierced tongue, asked, "Would you like another stud in your mouth?" She thought it was amusing. She also sent him packing.

One night at a corporate party, I was making small talk with a handsome CEO when he started persistently asking where I lived and if he could check out my bedroom. As I excused myself, he pulled me toward him. "tonight's the night, baby," he breathed into my ear. I couldn't help myself; I cracked up in his face. It was funny; it was also insulting and pathetic.

If you know for a fact that you're a funny guy, then be funny. If you're attractive, then show it off with nice clothes. If you're intelligent, strike up a conversation on some recent scientific discovery that interested you and will hopefully impress her. Even better, when you meet someone, find out what interests her with lots of questions. Chances are, if there's common ground to be had, you'll find it if you're patient and interested.

Location, location, location. There's a general and gross misconception that to effectively flirt, one must be at a bar or a club. In reality, there are few places worse suited for artful flirting. Approaching a stranger in a bar or a club is about as subtle as a bitch slap: establishing the common ground upon which to launch a friendly conversation is difficult at best. There's no pretext to approaching somebody in a bar other than the obvious: You're cute, lets go home and do it. No wonder so many people end up asking, lamely, "So, you come here often?" Whereas at a party, you can ask pretty much anyone, "So how do you know so-and-so?" and be off to a good start.

As evidenced by Richard's short, sweet encounter at the salad bar, good flirting can happen anywhere. While eating at a restaurant recently, Peter put down the book he was reading. A woman sitting near him picked it up and asked him how he enjoyed it. They started talking, and at the end of the conversation, she gave him her number. Flirting can happen at the gym, the supermarket, stoplights, in elevators, chat rooms-pretty much anywhere you might go. As with being an effective Boy Scout or not becoming an unplanned parent, the key to artful flirting is to always be prepared. You never know when you're going to meet somebody worth talking to.

Of course, it's one thing to itemize the steps to better flirting. It's quite another to hit the streets running. "Flirting is a behavior pattern. It's who we are, it's how we behave in the world," Gentille says. "It's not easy to change from an ineffective way of behaving to an effective way of behaving. It takes commitment - a commitment to become a great flirt and a better person."

Instruction worked for Peter. After some coaching by Gentille, he tried a new twist on his old tactics. While running across the street to buy cigarettes, he passed a bar and noticed two girls inside looking at him through the window. He smiled. They smiled. So he ran in and bought them drinks. Now here's the key: he then returned to the party he'd been attending across the street.

"I figured by the time I went back, they'd be gone," he recalls. "But they were there. I ended up talking with one of them for a little while. We had a lot of laughs, enjoyed each other's company. We ended up kissing and I got her number. It was nice."

Peter scored because of two things: he took a more low-key, casual approach and, despite getting his clock cleaned at the Casanova, he never gave up. Classes, books - even articles in men's magazines can all help the average joe turn his flirting method into art. But, with rare exception, good flirts become so only with plenty of practice. So the next time you're getting gas, thumbing through fiction at a local bookstore or piling carrots onto your salad, be prepared to lay on a little of the old charm. Who knows? Practice could lead to perfect on the first try.

San Francisco-based writer Jenn Shreve once flirted her way through twenty dates in twenty nights for P.O. V.' s sister publication, Egg.