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“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.

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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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