Professional Wingmen Will Get You Laid for a Price

By Craig Stephens

Trying to pick up a person while grocery shopping, in a park, on a train, or at a traffic light seems to be a lost art. Such weirdness is considered to be an awkward maneuver used by outmoded Luddites, sad freaks who aren't savvy enough to navigate online dating options available to anyone with a computer.

Still, whether its attributable to blind nostalgia, raw non-conformity, or just a poor internet connection, these folks continue to exist. Haplessly bolstering their efforts with new clothes, scents, and social dithering fuelled by increasingly precious cash, they still trudge out into the night (and day) to stalk their prey. Yet, without the reassurance of a buddy/friend/wingman or wingwoman, they are deemed desperate, weird, sadly unpopular, and friendless—an obvious disincentive for a potential “mate.”

A wingman/wingwoman/wingperson personifies reassurance for the casual observer, particularly potential dates. Akin to a bodyguard/maid/butler/counselor they serve as a guardian, ego booster, and ornate decoration that suggests you are palatable to at least one other member of the human race.

It’s irrelevant who a wingman is, as long as they present well and speak kindly of you. They could be a long-time friend, work colleague, neighbor, or roommate. Unfortunately for some eager singles, finding a person to hit the dating scene with you solely for your benefit is difficult. Enter the paid wingman—giving romance-starved folks a second chance via a hired hand when they’re on the prowl.

Services such as Professional Wingman in New York and Wingman Pro in LA cater to the desperate and dateless. The former costs around $400 for basic services, with additional seminars, counseling, and classes on everything from dress sense to educated dining. A full blown wingman syllabus could set you back thousands of dollars.


Thomas Edwards, the "Professional Wingman"

Professional Wingman head honcho Thomas Edwards said, “We also have other high-level programs, including style consulting and online dating assistance. If the person isn't local, we'll offer on-demand coaching and Facebook consulting. We also have live events like 'Confidence Unchained,' staged in New York City."

Edwards said he conceived the idea for the business after he realized he could exploit his aptitude for socializing. Since June of that year, he's been making a living by giving clients pointers on their social skills, often accompanying them to social events and helping them to talk to women.

"I see what is preventing them from being successful and give them real-time feedback,” he said. Edwards's corporate shtick is a far cry from his humble beginnings. "I was at South by Southwest in 2009, and someone asked me to walk over to a girl and make an introduction. If I got the guy a date, he'd buy all my drinks for the rest of week. Well, I did, and I had an open bar for three days. The idea of being a wingman stuck in my head.”

Unlike the corporate largesse of Professional Wingman, its west coast counterpart, Wingman Pro, offers the same type of service, though a little more low key. Operating like an elite dating agency, Wingman Pro is a word-of-mouth operation, with clients needing to be introduced into the company by others.  

Owner Andre is an Iranian-born dude in his 50s, with the ominous credit of being a “self-made businessman.” He also invests in real estate, finances films, and manages talent. Andre said he got the idea of being a professional wingman after being repeatedly asked to line up girls for traveling businessmen in LA.

"The clients are just monied men who want to meet women," Andre said. "It’s no biggie, I don’t want to play pimp, and few of them want hookers. It’s pretty honest and simple, they want to meet women on legitimate terms, girls they might become friends with and see again when they are back in LA in future, though they usually don’t have the means, we give them the means.”

Andre said he has about five paid wingman on his books. Many are actors, some are models, and there are also some elite security guard types. After some lengthy convincing, Andre allowed me to discreetly tag along while one of his employees took a client out for a night. Rather than interact and complicate things, I kept a safe distance while the potential daters ventured to LA’s douchebag heaven, Sky Bar on the Sunset Strip.

Sky Bar is cheesy, crowded, and expensive, with criminally expensive $1000 bottle service. Amongst a sea of mini-dresses and matching dude uniforms, I lurked at the bar and honed in on Roger (name changed) and his wingman for the night, Todd, an LA-based actor from Chicago.

They avoided the line out front and strolled in. Full of swagger, they both shook hands with the mammoth doorman as they entered. Those patiently awaiting entry looked on enviously.

Roger is an industrial engineer from Frankfurt, Germany. He visits LA several times a year en route to Central America where he brokers deals for mining machinery and similar stuff. Slightly overweight, he wore the standard LA guy attire of polo shirt, khakis, and boat shoes. Despite being 45 and balding he didn’t look that out of place, though Todd is about a foot-and-a-half taller.

Black, athletic, and brandishing the look and confidence you’d expect of an actor, Todd said of his sideline career, “It really is the perfect job for an actor. You play a role and you use your looks to help a guy out with the ladies, everybody wins. It's also about SAG rate for a bit part and it's done in just a few hours. I’m happy with it.”

“I also feel really good about helping these guys out. They have no real knowledge of LA and would either end up just bar-hopping or lining up a skanky hooker for the same amount they end up paying me.”

Todd and Roger are unlikely friends, though to the two Korean-born, part-time students whom they were chatting to, all is well. Roger beamed as the pair sidled up to the bar, initiating conversation with a pair of beauties out for some subsidized drinking. After two rounds  they paired off and dabbled in some dancing. Roger landed one of them and seemed quite content, revealing details of his travels and babbling pleasantly.

A lengthy 55 minutes later and it was all over. The girls had to head back to be fresh for their respective part-time jobs on Friday (or so they claimed). Still, for Roger it was not such an anti-climax, as he scored a dinner date on the following Sunday. He later pondered local spots Pink Taco or Chateau Marmont, though he eventually settled on the former. “It’s a first date anyway and I don’t want to go overboard after all.”

More on dating:

Five Tips for Ruining an Interracial Relationship

The VICE Guide to Dating Rich Girls

All Around Losing - Dating Is Terrifying

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