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There didn’t seem to be anything wrong with the man sitting across from me. I had yet to detect a single flaw in his appearance, speech, or demeanor. His hair was black and wavy, his eyes blue; he was muscular and lithe at six foot one and 200 pounds, square-jawed, and comfortable in his skin. His conversational skills were better than average; the more he spoke the more likable he became, revealing a well-developed sense of humor and a healthy dose of humility that offset the quiet confidence he exuded. Even his table manners were up to par — while eating the meal for which I’d invited him out, he sliced rather than stabbed his skirt steak and opted to sip instead of gulp his wine. This strapping, corn-fed 26-year-old would be the one to beat at a casting call for the next Superman movie. It was difficult for me to imagine why such a specimen of male perfection would hire a woman to help him meet other women. But two nights earlier, that’s just what he had done.

“Mark Anderson” — so dubbed by me because of his reluctance to be known — recently moved to San Diego from a small town in Iowa. “All my friends were getting married. They do that about this age,” says Anderson. “I didn’t like my job as a retail manager. I got bored. It’s hard to find single girls my age in that area, and if you do, they all want to settle down right away.” A friend invited Anderson to visit him in California. “He showed me a great time. I quit my job, sold some of my stuff, gave some of it to my friends and family, hired a moving company, and just moved out here.” Two days after interviewing for a temp agency, Anderson was assigned a permanent job in an office. “I was always worried about money in the past. Now I’m able to go out and have a good time. For once in my life I don’t have to work weekends and nights, and I’m going to enjoy that for a while.”

Once here, Anderson was quick to make new friends, but a few months passed and he had yet to go on a date. “I tend to be very shy,” he says. “I’m from a really small town — a graduating class of 35. My whole town was, like, 1000.” In high school, Anderson was neither the most popular nor the most picked on. “I was stuck in the middle, which is actually the worst. A lot of those small-Midwestern-town stereotypes are true — the starting quarterback is going to be your most popular guy in school. I was not the starting quarterback. I was the tight end. It’s not as glamorous.”

Like any shy guy, Anderson has difficulty speaking to women. “If I’m interested in someone, my brain freezes and it’s just a cloud and I can’t think of a thing to say. I’m literally that guy who walks up to a girl and thinks she’s attractive, and I go, ‘Hi…’ ” He freezes and stares blankly for a few seconds to illustrate. “I’ve been single a very long time [a year and a half], and it’s kind of like, ‘Okay, I’m ready to have a girlfriend.’ ” Before moving to San Diego, Anderson had dabbled with craigslist, MySpace, Match.com, and Yahoo! personals, but this time around, he decided against online dating. “To be honest, I’m just a little too lazy to do all that work — I’d rather meet somebody in person and know right off the bat if I have that connection with her. Every girlfriend I’ve ever had, we just immediately had great chemistry, great rapport, and I just knew I had to date this person. I don’t run into that often, and I definitely don’t think I’d get that online.”

A Wingwoman Is Better Than a Wingman

One August afternoon at a coffee shop in Pacific Beach, Anderson noticed a pink business card pinned to the bulletin board. It said, “Bar Buddy San Diego: Because a wingwoman is better than a wingman.” Anderson pocketed the card. “I thought, why not? It could be interesting. I knew about Wingwomen [a dating service in New York that opened in December 2004]. I’d seen them in Maxim and Playboy — I actually read Playboy, the articles are very good.” That night, Anderson emailed the address on the card and booked himself a bar buddy for the following Wednesday.

Most singles are familiar with the term “wingman,” used to describe the supportive male friend of a guy engaged in the art of seduction. In the Air Force, the wingman protects the lead aircraft in an attack formation. The term was most likely adopted by single men because of the strategic and predatory nature of hitting on women. The analogy can stretch to accommodate almost all aspects of dating: think of the phrases “he has her in his sights,” “slipping in under the radar,” “mission accomplished,” and the commiserable “he was shot down.” As a result of being pursued in this manner, women in the dating scene have their defenses up and can easily recognize such formations. Now, with companies like Bar Buddy, Wingwomen in New York, and Venus Allure in Washington, D.C., men have a new and improved strategy for pursuing women.

Bar Buddy was founded in the summer of 2007 by Matt and Rick, two twentysomethings who requested I not share their last names. They met through craigslist, when Rick answered an ad to design a website for Matt. To pay his Mission Valley rent until the company takes off, Matt works as a computer systems administrator. He is tall and thick, with a baby face and dark hair. Matt celebrated his 21st birthday just a few months before launching the company that relies on the hundreds of bars he is now legally allowed to enter. He initially wanted to open a franchise of Wingwomen, but the company’s owner, Shane Forbes, was not interested. “I asked, ‘Do you mind if I steal your ideas?’ and he said, ‘No, but do not use the word “wingwomen.” ’ He was very nice; he gave me the rundown in three or four hours.” Matt and Rick designed a website that could be easily accessed from a BlackBerry. “Even the form can be filled out on a BlackBerry,” says Matt. “Our target audience is 25- to 45-year-old men who have a higher-than-average disposable income. Of that, a pretty good portion are on mobile devices.” He adds that this feature will cut down on the possibility of a man becoming embarrassed if a coworker “sees over his shoulder and recognizes the website. Guys shouldn’t be ashamed, but they probably wouldn’t want to advertise” that they are using the service.

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shizzyfinn Feb. 13, 2008 @ 8:46 p.m.

So if, with his wingwoman's help, a guy does meet a woman that he wants to date, does he tell the new woman that the woman he was with was an escort? That could get weird. But the cover-up could be worse than the crime. What's a nice, sensitive guy to do?


Barbarella Fokos Feb. 15, 2008 @ 9:02 a.m.

That's the question, Shizzyfinn. I leave it to the nice, sensitive guys to answer for themselves. ;)


MikePhace Feb. 16, 2008 @ 5:09 p.m.

I would say that I was out having a drink with someone from work or an old friend who was in town visiting the area. That's too easy of a question to answer....

I like the service and I would utilize it if I didnt have any cute female friends. Women are very weird....when they see a guy with a cute female or a few cute females they become disarmed and curious. If you roll up with dudes the only women you will have luck with is girls on the rebound or barflys....all of which are nothing to take home to mom.


Josh Board March 4, 2008 @ 2:46 a.m.

Just got around to reading this. Very enjoyable story. I'd have to say...the guy would be INSANE to ever admit he hired a "wingwoman" to the woman he met and is dating. Because, there can just so much about that that turns this new girlfriend off. Most women like a guy that has confidence. They might think shy guys are cute, but when it comes down to it, they like a guy to have enough confidence in certain aspects of their life. And, them finding out you hired a woman, and that's how you met them, just reeks of patheticness. And, it also can be seen as deceitful, as this "wingwoman" vouched for you being a good guy. And, well, she really doesn't know you're a good guy. She was basically hired to say that. So, it starts the relationship off on a series of lies.


wingwoman3 Feb. 13, 2011 @ 4:30 p.m.

Having a girl that's confident and able to open conversations with strangers can make or break an interaction. Being a hired wingwoman is definitely a great way to meet people are make a little money on the side. I'm with a wingwoman service called Chicago Wingwoman at www.chicagowingwoman.com. Check 'em out!


tootit Nov. 8, 2011 @ 2:01 p.m.

This comment was removed by the site staff for violation of the usage agreement.


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