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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.

Matt stresses that Bar Buddy is not an escort service. “The girls are not going out to be your arm candy for the night; they’re not going out to be your date.” For $50 an hour, a man can employ a “bar buddy” to accompany him to a social event or bar and break the ice between him and any woman who interests him. Of the $50, the woman gets $20. “As we get a little more busy and are sending girls out on multiple dates, we will try to send feedback forms. Obviously, the better a girl scores, the more her rate is going to be.” After a five-outing probationary period, the woman’s pay is bumped to $25. Eventually, a bar buddy can make up to $35 per hour.

“We get somewhere in the range of 10 to 15 emails a week from girls who want to be bar buddies,” says Matt. “We probably receive 6 to 10 emails a week from guys. Unfortunately, a very small percentage of them end up panning out.” So far, the company has had about a dozen clients.

Rick, a superfit cutie with light eyes and sun-bleached hair who reeks of quarterback, is responsible for compiling what he says is a collection of attractive, sociable females aged 21 to 35. Matt doesn’t expect older men to use his service, but if they do, they would most likely be paired with a younger woman. “Whether it’s right or wrong, a lot of the guys in their 50s are going to bars looking for 21-year-olds anyway.”

The prime objective of a bar buddy, Matt explains, is “obviously a phone number,” but he emphasizes that there are no guarantees and that it is better for a client to make one real connection than to collect a long list of numbers.

“The main goal is for a guy to feel satisfied,” says Rick. “This is a matchmaking service, so building up his confidence is one thing I harp on the girls to do. If he feels satisfied, if he’s out there meeting girls and talking to them and having fun, that’s going to do it.”

Barbarella, Volunteer Wingwoman

According to Bar Buddy’s website, “Studies have shown that it is easier to meet women when you are introduced to them by another woman.” My personal experience corroborates the statement. Countless male friends have me to thank for dates they’ve had with women I introduced them to. Once, while sipping on a cheap and strong cocktail at Nunu’s, my friend Randy gestured toward a girl at the bar and said, “She’s so beautiful. I could never approach her. How do you talk to a woman like that?” “Wait here, I’ll show you,” I said and left my friend to stand alone while I sidled up to the bar next to the woman and ordered another drink from Jeff, my bar buddy.

While I waited for my vodka concoction, I turned to the girl and said, “Your brows are perfect. You do them yourself?” Thus we were speaking. Several minutes later, Randy appeared at my side, and I casually introduced him. “Oh, hey, Lisa, this is my friend Randy. You know, it’s funny, you were just talking about how much you love the museum, and Randy here volunteers as a docent there once a month. I’ve got to use the restroom. Will you two watch my drink for me?” By the time I returned after half an hour of chatting with other friends, Randy and Lisa had exchanged contact information.

Morgan Gill, Paid Wingwoman

“You kind of act like his sister, his friend, or the girlfriend of his brother’s buddy,” says Morgan Gill, who’d been Anderson’s assigned bar buddy two nights before he met me for dinner. “You help break down the barriers that women instantly put up when they go out into the bar scene.” Anderson was her first (and, at the time we spoke, only) assignment in San Diego, but Gill had been on many such outings while working for Wingwomen’s Seattle branch. I met up with Gill one breezy, overcast August afternoon at a Starbucks in Clairemont Mesa. Her pink blouse and printed skirt ensemble was feminine but professional, and not a strand of her thick, straight dark hair was out of place. Her coloring, high cheekbones, and small, pretty features reminded me of Catherine Zeta-Jones. In addition to her day job as a project manager, Gill runs a relationship consulting business called Proper Me. She found Bar Buddy through its ad on craigslist.

Gill describes Anderson as “an attractive, six-foot-four guy who works out on a regular basis and has dark hair and very strong, manly features.” She says he is a “prime candidate” for her consulting business, “because he grew up in a very small town and didn’t have a lot of women to talk to.” Such men, Gill says, may need to be coached on the “rule of a thousand no’s,” which she defines as “It takes a thousand no’s to get a really good yes. Guys who live in cities, they attest they’ve all had a thousand no’s. That’s why they have the confidence they have now. I’ve worked in sales a lot in my life — most people are afraid to approach people they don’t know, because they’re scared of what they’re going to say to them. They can’t handle [rejection], but if you asked a lot of people and they all said no in any way, shape, or form, what’s the fear now? You’ve already been told.”

Gill contacted Anderson by phone to establish a time and place to meet. “It was hard to get him to call me back,” she remembers. “It’s that fear thing.” It is up to the bar buddy to work out the venue for an outing; the decision is based on the client’s interests, availability, and location. At no point is a bar buddy supposed to get in a car or taxi with her client. If she and her client decide to leave one club and go to another, they should walk or take the trolley. If a bar buddy becomes too drunk to drive, Rick says he would pick her up or pay for a cab, because “that’s part of the job, where they’re going out and guys are buying them drinks — they don’t have to drink, of course, they want to keep their wits about them because they’re on the job, but if they do.” When Gill finally got hold of Anderson, she suggested they meet at In Cahoots, a country-western nightclub in Mission Valley, and she emailed a photo of herself so that he would recognize her.

“I talked to him a little bit out in the parking lot before we went in, just to get the story straight, because once you get in the bar it’s hard to talk,” Gill says. “The longer I spoke to him, the more outgoing he became — he’s got a great personality, a great sense of humor. He’s really a nice guy. I was, like, ‘Oh my God, I could think of a few girls I would try to hook you up with,’ and when I brought that up he turned a little red and got shy, and I was, like, ‘Oh God, he’s so cute it’s ridiculous.’ ”

On his way to the club, Anderson was nervous but optimistic. After introducing herself, Gill asked Anderson a series of questions so she could get a feel for the type of woman he might be interested in. It wasn’t long, Anderson recounts, before they were comfortable enough to joke around. “I was laughing in the parking lot because there were pickup trucks everywhere, and I was, like, ‘I don’t see many farms around here.’ And a bunch of guys in cowboy hats; I was, like, ‘This was why I moved away from the Midwest, and I end up back in it.’ Actually, I was laughing at them because I don’t understand cowboys in San Diego.” Though Anderson found Gill to be attractive and “easy to talk to,” he had ruled her out as a prospect before meeting her. Aside from the fact that she had a boyfriend, Anderson says, “I went into it knowing I’m not even going to attempt anything with [the bar buddy]. But if I just ran into [Gill] randomly at a bar, it would be completely different.”

Gill says she could tell what sort of women Anderson was attracted to just by looking at him. “Somebody who takes good care of himself is going to want to be with somebody who takes good care of herself”; in other words, if he’s hot, he’s going to want to be with somebody who’s hot — and not somebody who’s not. Gill’s first glance inside the club revealed dismal options. “There was a sea of 20- to 30-pounds-overweight women in wife-beaters and no makeup, and I knew that wasn’t [Anderson’s] cup of tea. I didn’t want to say anything, so we kept walking and I thought, ‘Okay, maybe this is the initial crowd, and maybe once we get inside, we’ll find the hotties all in the back.’ So we start walking around, and we did a couple laps, but there just weren’t a whole lot of interesting people there or people that I thought he would find interesting.”

Anderson claimed that he was not attracted to any specific type of woman, but after 20 minutes, Gill deduced that he had a thing for brunettes. “And then he started going for the brunette-exotic look — a little darker skin, darker hair, a more ethnic look. He really liked that, but I’ve got to say, 95 percent of the men I know go for that right off the bat. An Indian, Persian, or in this area, a very well-kept Latino girl. It’s just exotic. It’s not something you see every day.”

Eventually, Anderson pointed out “one of the exotic-looking gals” across the dance floor. Gill said she’d watch the girl for a while and try to determine if she was single. “You don’t want to go up to somebody who’s obviously with a guy. That’s just not cool.” After watching for a few minutes, Gill could see the woman was at the club with a group of women. “The first thing that came to mind was, ‘She’s here with a bachelorette party.’ The second one is that she’s doing a girls’ night out kind of thing. Now, traditionally on a girls’ night out, most of the girls have boyfriends.” Gill had the feeling this girl was taken, but she wanted to make sure. She instructed Anderson to go stand near a group of people so that he didn’t appear awkward. Anderson obeyed and did his best to look “approachable but busy.” Then Gill made her move. “I approached her, and I’m just, like, ‘Hey, my friend over there thinks you’re really cute,’ and she’s, like, ‘Which one?’ and she looks all interested.’ ” Gill pointed to Anderson, and the girl said she thought he was cute. Gill recalls, “I’m, like, ‘Yeah, I know,’ and she goes, ‘But I’m married,’ and she pulls her hand up, and there’s this huge rock on her finger, and I go, ‘I knew it! You’re here for a girls’ night out, aren’t you?’ and she’s, like, ‘Yeah.’ ”

In a “separate the prey from its herd” maneuver, Gill might follow a woman to the bathroom to strike up a conversation and do reconnaissance on behalf of her client. Anderson selected a second girl, who was surrounded by men. “I kept waiting and waiting, and she just was not branching out from the group,” says Gill. She was able to obtain the woman’s name (by overhearing someone else say it) but hesitated to bust into the group. She suggested they keep looking while waiting for an opportunity to address the girl. Anderson then pointed to a blond. “I was, like, ‘Oh God, here we go,’ ” Gill says. “Out of all the girls that he’d been pointing out, this one really didn’t fit the mold. She was bleached blond, lots of makeup, really overdone, and she continually danced with guys that were 50 or older.” Regardless of her personal feelings, Gill says, “I was, like, ‘Uh, okay, you want her, I’ll go get her.’ ”

The blond wore a “classic little baby-doll shirt tied in the back, which came down almost covering her entire really short shorts.” Gill guessed her to be 26 but says the layers of caked-on makeup made her look around “32, trying to go for 26.” Each time the woman appeared to be leaving the dance floor, another older man would cut in and back out she’d go. Gill told Anderson, “Okay, you hang out over here, and I’m going to try and grab her when she comes off the dance floor.” But when the next song ended and Gill opened her mouth to say hi, “Literally, a guy got his hand on her arm as I get her attention, and I’m, like, ‘Are you serious? She’s got one leg off the dance floor and one leg on, give me a break.’ The guy looks at me, like, ‘She’s mine,’ and I’m kind of, like, ‘No, she’s mine,’ and he goes, ‘Oh, you want her?’ and I’m, like, ‘I can’t have her for, like, two seconds?’ and he’s, like, ‘Okay,’ and he goes away.” Meanwhile, the object of Gill’s dispute laughed at the fun of being fought over.

Once she had the girl’s full attention, Gill employed her well-worn “Hey, my friend thinks you’re cute” tactic. She asked the woman if she would come by and say hi to Anderson when she was finished dancing. “I really like to dance,” said the girl. “Yeah, I know, I can tell,” Gill responded. From where they stood, the blond could not see her admirer. She said she would try to stop by later. “Three songs later I’m noticing she’s cycled through three different 50-year-old-looking guys. None of them were attractive, and I’m, like, ‘Seriously,’ you know? She had a couple of earrings in her lip, and I’m really not thinking [Anderson’s] going to be into her. She is not his type. Needless to say, she never came by.” Gill waited for Anderson to bring it up. Eventually, Anderson said something. “He’s, like, ‘She’s not coming.’ I said, ‘You’re better off. Frankly, I wouldn’t be surprised if she’s a gold digger, and she just doesn’t seem to be interested if you’re under the age of 49.’ ” Later, when Anderson was able to get a closer look, he agreed with Gill’s assessment. “So that turned out for the better — either she would have expected payment at the end of the night or she would have expected a diamond ring, one or two, which she wasn’t getting either.”

The fourth woman to spark Anderson’s interest had a girl-next-door look about her. Her brown hair was in pigtails, she wore overalls, and her face was fresh. Gill thought she was “way too cute” to not have a boyfriend. Other clues tipped her off as well: “She just looked very comfortable with her surroundings, she really wasn’t trying to overdo anything, she was just happy with who she was. When I see a girl like that I’m, like, ‘Oh, she’s taken.’ ” Anderson wanted to be sure, so Gill continued to monitor the woman. “Sure enough, a few minutes later, a real happy-looking little guy comes bouncing along, puts his arm around her, and they just look like a happy little couple.” Anderson was disappointed. If prior to meeting him Gill had had a clearer understanding of the type of women Anderson liked, she says she would have taken him elsewhere. “I go, ‘You’re looking for a girl in all the wrong places. One, you’re probably not going to find her in a bar and be able to talk to her, and two, you’re in the wrong part of town — you need to go down to P.B.’ ”

“There’s really not even a handful of girls I personally found attractive there,” says Anderson. Still, he considers the evening a success. “I did something new, and that’s something in my hometown that I never would have done. I never would have gone out with a complete stranger to try to meet other people.” Even though he didn’t find Miss Right, Anderson still believes his chances are better with a wingwoman. “I don’t know if ‘science’ is the right word, but whatever is behind it, I read a lot of articles on the Internet, and I’ve read so many studies that prove when a guy has a woman with him — it’s even in the brain patterns of other women — not only do their defenses go down, but they literally find him more attractive because of the competitiveness, especially if it’s another attractive woman. Women want what other women have. Studies have also shown they find a guy more trustworthy, easier to approach.”

What Came First, the Bitchy Woman or the Overaggressive Man?

Gill says this phenomenon is especially true in San Diego, where the women are “more difficult” to approach. “I know about 20 single guys, and they’re all perfect. I would hook them up with a girl any day of the week. But they’re all single, still. They go out every single weekend looking for girls, and they’re dressed nice, they’re attractive, they make money, they have great senses of humor, great personalities, and I am just flabbergasted as to why they can’t find quality women.” Gill blames this on the women of San Diego, who she says are particularly punishing. “If you’re a decent-looking girl, and you have a decent-looking guy approach you, why are you being bitchy?” Gill says many women in town expect men to buy them drinks. If one doesn’t, the women “just get this attitude. They think it’s funny to go out and not spend a dime.”

Al Smith, a notoriously single friend of mine, agrees with Gill’s assessment and adds that there’s a tendency among Southern Californian women to have unrealistically high expectations. An attractive thirtysomething from Indiana who works in a senior position at Qualcomm by day and plays a pedal steel guitar in a band by night, Smith has met too many women who seem “to be more about what you can do for them than they are about finding someone to go on the journey of life with.” He says there’s too much emphasis placed on how much money a man makes, what kind of car he drives, and where his condo is situated. “It seems like a lot of the girls I’ve met in the past, they don’t look at you as a person as much as they look at you as a reflection of themselves and their status, and I think that comes from insecurity,” he says. “It’s almost like they want a trophy man.”

But shallow women are only one side of the bitchy coin. “When I first came here as a single adult,” Gill remembers, “I was shocked by how aggressive the men are here.” On several occasions, Gill has literally had to push away men who grind against her in bars. “It makes me really uncomfortable when I have to become bitchy.” Sometimes, she concedes, being rude is the only way for a woman to get her message across. One night, while dancing in the Gaslamp, Gill and her girlfriends were surrounded by a group of men. “They were, like, herding us together. It got to the point where the girls had to start dancing with each other, just because if you danced openly, a guy would come up to you.”

Regardless, Gill says women should not allow bad behavior to transform them into bitches. “If there’s one thing I can impart to the women of San Diego, it’s be nice. If a girl approaches you and says, ‘Hey, my buddy thinks you’re cute,’ just be open, don’t shoot her down right away because you don’t know her. Don’t necessarily be nice to the guys grinding on you, but be a little more open to the guy who’s not grinding on you, the guy who’s not telling you he’s going to buy you a drink — be a little more open to the guy who keeps looking at you from across the bar.” For men, Gill says, “As sad as this sounds, I would tell them to be a little more creative with how you meet a girl. Don’t walk up to her and start grinding on her.”

Gill refers to the San Diego club scene as a “vicious cycle” of extremely offensive men begetting extremely defensive women. “Like the chicken or the egg, it’s like, what came first? The bitchy girl or the aggressive guy? The girls just keep getting more standoffish and walled up and ‘Get away from me,’ and the guys just keep getting more and more aggressive to get them interested. I’ve been to Chicago, San Francisco, New York, Miami, Houston — I’ve hit the party scene in all of them, and I’ve never seen such an odd situation as this is.” When asked what she thinks is the difference, Gill responds, “I don’t think it’s the military men — military guys are very respectful. They’re the ones that will open the door for you, give you your coat; they will be more chivalrous.” She thinks it might be a form of desensitization, “Where there are girls with boobs and bikinis everywhere, there’s skin and alcohol everywhere, it makes the men like piranhas. It’s a feeding frenzy because there’s blood in the water.”

Gill feels a hired wingwoman — because she is more invested in the guy’s success — is more effective than a female friend who might be doing a favor. “There’s just way too many variables,” she explains. “I think it might have to do with female insecurities; some girls don’t have it in them to approach others. It might be that they’re single and could be that they’re interested in the guy that they’re with, and they just don’t say anything. Even if she’s not single or interested in him and knows it would never work, there’s this weird ‘Why aren’t you interested in me?’ It’s just this bizarre competitiveness.” There is the possibility, Gill adds, that “the girl friend could be interested in the guy and may not want to hook him up with someone else, or that she may want to spend some time meeting men, whereas I’m here to answer questions, help you fit in, help you navigate, tell you, ‘Hey, I wouldn’t do that one if I were you. I’d go after somebody else.’ ”

Bar Buddy Psychology

Gill admits there are downsides to Bar Buddies that she does not encounter in her consulting business. Whereas a woman might be flattered to learn that her man had hired a consultant to help him meet or woo her, she might be put off that he’d hired a wingwoman to help him meet a number of strangers, one of whom happened to be her. “The guys are embarrassed,” Gill explains, “because they have to admit they have problems meeting girls, that they’re not at the top of their game. It comes down to primitive nature — all gatherer women want hunter men, and if they think he isn’t the hunter they think he is, then there’s some psychological thing in the back of their head that says he’s not the one for me. So when a guy gets nervous and says, ‘I’m scared to death to say I had to hire somebody to help me out,’ what’s the matter with that?”

According to Dr. Richard Jordan, a local psychologist who specializes in relationships, there’s plenty the matter. “It’s kind of a good news/bad news if it works,” says Jordan. “The good news is, obviously you get paired up with somebody, and that might be a very cool thing. The bad news is — okay, just imagine that a guy meets a girl this way, they go out a few times, and she asks about his ‘friend.’ She might say, ‘Oh, that sure was a cool friend. Tell me more about her. Did you guys ever date?’ There’s going to come a point somewhere in the game, if they get far enough along, when either he’s going to have an ongoing secret he’s going to have to lie about for the rest of his life or [he must] cop to, ‘That wasn’t really my friend,’ and the whole foundation and heart of their initial meeting comes into question.”

The two guiding principles of Jordan’s practice, he explains, are truth and responsibility. “Truth: not only being honest but to tell the truth about what I’m experiencing right now and to share that with my partner. Responsibility: being responsible for any feelings or issues that come up, saying what’s my part in that and taking responsibility.” If you begin a relationship under false pretenses, Jordan says, “Whether [the woman] is willing to overlook [the lie] or not, it is something that would have to be overlooked.”

My friend Al Smith says that he wouldn’t be comfortable with meeting a woman under such circumstances. His reasoning is similar to Jordan’s. Smith says, “You’re kind of starting the relationship, or whatever it’s going to be, off on a lie. You may not be completely misrepresenting yourself, but you’re certainly not being honest either.”

Small fibs, says Gill, are sometimes necessary in order to weed out undesirables. In her consulting business, she advises her wealthy clients to keep their credit cards close to their chests. One such man lives in Los Angeles and makes at least a million dollars a year. “He’s attractive, fit, personable, travels the world in his free time; he has a hard time finding a girl who’s genuine,” explains Gill. “He meets the gold diggers, and he has to be very much on his guard, and he has to play games.” Gill advised the man, who drives an expensive Humvee, to get an older vehicle, or “beater,” and drive that on the first date. “A lot of these guys that are driving these really nice cars, have really nice houses, making money, I guarantee you that they have a beater they drive.” If the woman is not “put off” by the homely vehicle, the man should feel safe to take her on a second date. He should not bring her back to his house “for the wow factor” until the fourth date. “But he still should not open his garage for her,” Gill says. And, she counsels, he must wait at least six months before introducing her to his friends and family.

Before any man requires dating advice, however, he needs first to meet a woman in whom he is interested. Despite Anderson’s failed missions in this regard, he remains optimistic. He may have trouble approaching women, but once he’s introduced to one, he is confident of success. Of other guys he’s witnessed while out and about, Anderson says, “I don’t think they were brought up well. There’s no way I could see a woman walking down the street and go, ‘Hey, baby, how are you doing?’ My family raised me right.”

After finishing his steak and taking the last sip of his wine, Anderson checks the time on his cell phone. I’d had him meet me for dinner at Bite in Hillcrest, and by now his friends would be waiting for him at a bar downtown. “Male friends?” I ask. Yes. “Are you out looking for girls?” Always. “How are you going to go about meeting them?”

Anderson pockets his phone, stands, and flashes his perfectly straight pearly whites. “I don’t have a tactic,” he says and shrugs. “I don’t know. I’m just a nice guy.”

“Well, then,” I say, raising my glass. “Here’s to you meeting a nice girl.”

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Comments

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?

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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. ;)

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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.

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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.

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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!

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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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