Friday, July 18, 10 p.m.

It’s hard not to feel just a little like a hooker when you’re dressed to the nines, waiting for a man you couldn’t pick out of a lineup and whom you only know by his first name. For obvious reasons, we’ll call him John. I meet up with my mentor, Shilo, outside Blue Martini. Over a round of drinks, we talk.

Tall, blond, 24 and Vegas-born and raised, Shilo (again, first names only) is instantly disarming, naturally outgoing. Between sips of her cocktail she explains her role as a professional wingwoman for Wingwomen.com, a company which has been paving the way for New York’s single men to get women’s digits since 2004. The service begins in Vegas tonight. “You have to be able to talk to other women in a way that they feel very comfortable. Be natural, be very outgoing.” Her background in promotions is a boon, as is the soothing manner she’s cultivated through the years luring pretty girls to VIP booths to keep a party appropriately stocked with beauty.

The term wingman (and not long after, wingwoman) harkens back, at least for me, to 1986’s Top Gun. In the military sense, it’s the pilot who maneuvers his aircraft just behind and to the side (at the wing) of the leader. In the social sense, it’s your buddy. He or she has your back and is more than willing to fib about your athletic prowess or age.

“A lot of it is getting to know your client,” Shilo explains to me, her attentive pupil and—if John should ask—an apprentice wingwoman. “You weed out 90 percent [of the potential targets] right off the bat.” Something of a mobile matchmaker, Shilo, like her counterparts in New York, will spend the first 45 minutes of her allotted two hours getting to know John. After that, she might excuse herself to go to the ladies’ room. There she might casually chat up a pretty 30-something with no wedding band about their similar taste in dresses. Back at the table, as the doppelgänger passes by, Shilo might invite her into their discussion and thereby introduce her to John. The two might even hit it off, exchange business cards, fall in love, get married and have babies! Or not. But John will have had a nice time and hopefully will go home with a handful of such opportunities for wedded (or at least bedded) bliss. Another satisfied customer.

Alas, Vegas is not New York. So in addition to hooking up single men, Wingwomen.com comes in handy for groups needing to pad their party with females at a nightclub. For $75 an hour per girl, according to owner Shane Forbes’ website, guests can book a single wingwoman for a one-on-one experience like John’s or two or more wingwomen for a club experience. “Vegas is a different animal than anywhere else in the world,” says Forbes, who resides in Miami and runs the New York office remotely; his new partner Noah Auspitz oversees Vegas. Exclusive to Sin City, the Rockstar Package tacks on VIP services such as limos, VIP tables, personal security and more, a fact that is very irksome to Las Vegas-based WingwomanTours.com.

Tuesday, July 22, 10 p.m.

Racheal arrives, tan and leggy and as toned as a professional dance instructor should be. At 10:30 p.m., she explains, she’ll meet John from San Diego (this time I’m not even giving him a pseudonym) outside Studio 54. But Racheal’s mission varies slightly. Her task, according to Wingwoman Tours’ mission, is to make a party of John’s night, not so much introducing him to women as introducing him to Vegas and making him feel comfortable in a club. And all the while, she will be shadowed by hired security for her safety.

Owners Lory Ambrosini and Kim Ehler’s site services men and women, straight and gay. “You’ve got your general-admission line, your VIP line and your Wingwoman Tours line,” says Ambrosini. Racheal’s mission: get the tour group in, get them to the bar, get them to the VIP section—and what happens next depends on the client. Wanna dance? Racheal knows swing, Latin, country and ballroom. Another wingwoman will find you the best tattoo in town or help you “jump out of a perfectly good plane,” says Ehler. They also count among their ladies a gambling expert, a chef, a famous actress and more. Ambrosini points directly at Racheal: “She’s beautiful, but she also has a brain in her head. ‘Pretty’ doesn’t cut it.”

Brains isn’t something I’ve encountered a lack of in this exercise so far. Both companies are stocked from the top down with innovative, entrepreneurial professionals. But there’s a tug-of-war going on at this very moment.

In a letter dated May 16, 2008, from the law offices of Mark Sherman in Connecticut, Forbes accuses Ambrosini and Ehler of “illegal use of Wingwomen LLC’s trademark in marketing materials.” Forbes’ domestic LLC, registered only in New York, is dated May 7, 2004. But his service mark “Wing Women,” filed on July 28, 2004, as a “dating service,” was abandoned on September 6, 2005, and is listed as “dead.”

In a response letter from the law offices of Barry Levinson in Las Vegas dated May 27, 2008, Levinson himself writes, “We deny your claim to exclusivity,” effectively telling Forbes to knock it off. “Wing Woman Tours” was filed on July 2, 2008, as a tour-guide service “with a personal flair” and is currently live. Therefore little is likely to come of Forbes’ complaint. Ambrosini and Ehler went beyond the required Nevada licensing, tax compliance and $10,000 surety bond, getting a $2 million insurance policy, as required by their soon-to-be affiliate Travelocity.

“Obviously they copied my product,” alleges Forbes.

“In a couple of months, the differences are going to become apparent,” answers Ambrosini. Argh! Legal stuff is tricky. But the proof is in the pudding.

Having been taken under the, er, wing of both companies, I can say that it’s the client who really presents the variety and the challenges. In the end, John No. 1 never showed up! Moving forward, it will be on the heads of Forbes/Auspitz and Ambrosini/Ehler to co-exist and to carefully weed through what the web brings them when they both officially launch in August.