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Photograph by Felipe Buitrago

The Playa: Our intrepid reporter on assignment, hitting on women with the help of a $50-an-hour companion.

A Friend in Need

For lonely single guys, a female wingman can help close deals—but at a price


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USUALLY THE HOMOGENOUS drones who populate the singles-bar scene do nothing for me, so the concept of utilizing a wingman never crosses my mind. But a certified female wingman? Now that's a phenom I had to hijack.

For those unfamiliar with the concept, a wingman is a male friend who helps break the ice with the ladies, continues the conversation and makes you look good in order to get the ever-important email address (the contact medium of choice these days, I've been told). He's supposed to help you get some action. I've never used this technique, so I can't vouch for its effectiveness, but it's a pretty common scheme.

There's now a new twist to the old game. Since two guys can be as intimidating as one, many bachelors have borrowed a female companion to help out with a hookup. For those men without even a single female friend, a professional organization, ladywingmen.com, has emerged. You can now pay a woman 50 bucks an hour with a two-hour minimum to emphasize what a swell, datable person you are. According to ladywingmen's website, its service "instantly legitimizes you to other women. You could be a total slobbering drunk, but if you're with a female friend, your slobbering drunkenness now becomes cute and endearing to other women."

With that clincher in mind, I contacted ladywingmen, which introduced me to a woman who went by the name of "Maria." She agreed to be my point person for a night pro bono. I agreed to keep her identity secret, though it's safe to say her brunette locks, fishnet stockings and cleavage instantly rekindled my fascination with the opposite sex.

She said she'd performed wingman-type services for her guy friends for years. "I didn't think about it as my soliciting guys," she told me. "I wasn't getting paid for it." We then hit the town to put her talent to work.

Maria already knew plenty about me, subjecting me to a barrage of friendly prying—nothing personal, just some basic questions about what kind of female I was interested in (underground, bohemian, counterculture, creative type with a Ph.D. and 12 piercings), how often I went on dates (rarely), when was the last time I had a long-term relationship (five years ago), things like that.

After the initial round of questions, the insidious details come next. Maria instructed me to show up well-groomed—no hair on the face, nose, ears or neck—and to wear an ironed shirt, not one that looks like it was yanked out of the hamper. She also said women don't like a guy obscenely doused in cologne or whose chest hair creeps out of the neckline.

"Standard operating procedure for dating, if you want to be successful, you have to go back to the old days a little bit," she said. "You have to be a gentleman. You have to act like you're interested, and kinda dress nice, or show interest."

"So it's not about going home together, watching a skate-rock video and drinking cheap malt liquor?" I asked.

"I don't even know what you're talking about," she replied. "I guess I'm removed."

Psych 101

Maria told me that she grew up in the 1980s sneaking into meat-market dance-hall places like Studio 47 and Paradise Beach—discos I wouldn't have touched with a 30-foot pole, even if I had been old enough to get in. So as a test I invited her to meet me at the opposite end of the nightlife spectrum—First Fridays at Anno Domini, a monthly counterculture art reception. It's the type of place that attracts art teachers, hip-hop heads and—most significantly—young alternative art-chick hotties.

Anno Domini was obviously not Maria's scene—she was too businesslike, perhaps, and was more interested in science—but she still moved effortlessly through the crowd. I was impressed with the way she initiated a conversation with women, allowing me to join in and eventually talk my way into closing the deal on some contact information. As we walked around sipping wine from a plastic cup, she approached a pretty woman in black boots, a skirt and red pullover jacket. Maria asked her if she liked the art show, which piece she liked best and so forth. At some point, I started chatting, not sure what I was saying. But at the end, I walked away with an email address and a tingling sensation from the flirting. Maria likens the lady wingman as a natural extension of the small jealousies common to pair bonding. If women see a guy in a bar hanging out with a female friend who's cool and tolerable, they'll become more interested in who the guy is.

"It's basically who you're seen with kind of reflects the friends you choose," she explained. "Women will size you up based on who you're with. ... It also goes with the basic Psych 101 where a woman wants something that she can't get and she likes that challenge, so she'll try and try and get to the guy because he's already with a woman. All of a sudden he becomes much more attractive." Maria emphasized a man should never inform a pickup that he used a wingman to get her number. "Don't you dare," she warned. "Don't even. Don't tell girls that stuff. ... You'll ruin your game." Not to mention her feelings.

After the art reception, we infiltrated what is left of the SoFA district, beginning with South First Billiards and its swanky Elixir Lounge.

Unfortunately, the heavy predominance of males to females prevented any serious prowling.

"It's all dudes," Maria observed. "Let's get outta here." As the band resumed their set in the front corner, we split in search of other joints.

We moved a block down the street to the new and promising SoFA Lounge upstairs above Eulipia—not a "pickup" joint by any stretch, but a cool, velvety, laid-back hangout nevertheless. By 10:45pm—still early—the male-to-female ratio clocked in at five to one. I had a beer and Maria ordered a French martini.

"You're up against a lot of competition here," she said as we slumped down into a vintage couch. "There's so many guys."

"Yeah, Silicon Valley is also known as Man Valley," I told her.

After our drink, we went down the stairs toward the sidewalk below, with Maria insisting that I let her walk in front of me. Two guys on their way up blatantly checked her out, but turned away when they realized I was with her.

"Did you notice that?" She said a few moments later. "That's important. That's why you let the woman walk in front of you, not behind. Guys will part like the Red Sea to let a girl go by. And you can give them the stare to let them know you're with her. Letting her walk in front also gives you a chance to check out the girl's ass."

"I've already been checking out your ass," I answered.

As we kept walking, I began to wonder if all this was really worth the $50-an-hour price tag. Except for the art gallery, I had nothing in common with the women in any of these joints, which included the next stop on our trip: Mission Ale House. Here the hunt continued, albeit for 30 seconds.

"This is just a frat party," Maria declared. "Forget it."

I agreed. The jock-to-female ratio was 10 to 1, and we left for a more interesting place down the street: Johnny V's, a killer hole-in-the-wall hipster bar where a DJ pounded out rhythms and disenfranchised types abounded. But unfortunately the only women worth hitting on were the cute bartenders. I was more interested in listening to what Maria had to say anyway. I crouched at the bar and pounded a few beers while she schooled me on everything from body language to leave-in hair conditioner.

My conclusion is that even if you have no problems picking up women, the lady wingman can still help you hone your skirt-chasing craft. She not only provides confidence, but I appreciated her advice. We talked some more about how to meet people. It's more like a job than I thought it was. "It's about getting the connections, just like networking for a job," Maria explained.

My night with Maria was over. I walked her back to her car, gave her a hug and watched her drive off. If only every woman were as easy to meet.

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From the February 16-22, 2005 issue of Metro, Silicon Valley's Weekly Newspaper.

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