Maybe you just got fired or think you're going to be fired in the not too distant future and would like to line up a new gig now. Maybe you're gainfully employed but looking to score some cash on the side. Maybe you're a humanitarian who wants to help the good if socially awkward men of the world get laid. Maybe you love hitting on women but would have a tough time explaining to your wife why they came home with you. If you've got both the skills to reel in the ladies (as well as the ability to separate the "fun-loving" pieces of ass from those who refuse to spend 10 minutes posing for pictures, the bitches) and the selflessness to offer them up to a brother in need, maybe you should consider becoming a wingman-- professionally. "But, Bess, do you really think people would pay me to help them pick up chicks?" Yes, in fact, I do.
Cort Johnson, 27, is an affable guy who's skilled at promoting his company—a mobile-application start-up he co-founded. But when it comes to socializing, especially with women, he tends to clam up. "I'd like to be romantic," he sighs. "But how?" For Mr. Johnson and many others, the answer is "hire a coach." Hoping to meet some prospects at a holiday party in December, Mr. Johnson enlisted Thomas Edwards, who runs a service called "The Professional Wingman." For a fee of $125, Mr. Edwards accompanied Mr. Johnson to the event and posed as his good pal. As they negotiated the crowd, the wingman alerted his charge to flirtatious types and helped make seamless introductions.
At the Boston holiday party called "Ugly Sweater Night," Mr. Johnson had slipped in with his wingman. Revelers, dressed in blinking Christmas sweaters, sipped bottles of beer and shimmied to the rap song, "Bust a Move." Mr. Johnson, wearing a Santa hat, scanned the room and homed in on a blonde woman in reindeer ears dancing with two friends. "She looks fun," he told his wingman. "I'll go in," Mr. Edwards replied. Moving quickly, he saw that one of the women had a camera and asked if he could take the group's picture. Giggling, they huddled together. But when a few people behind them tried to squeeze into the picture, the women stopped posing and looked annoyed. In their pre-event strategy session, Mr. Edwards had determined that Mr. Johnson is inclusive and fun-loving and needs the same in a partner. He backed away and shook his head at Mr. Johnson, signaling that the young woman wasn't worth pursuing. "I'm an extension of Cort. If that turned me off, it will definitely turn Cort off," said Mr. Edwards...near midnight came Mr. Johnson's breakthrough. A woman he had talked to earlier, and had liked, sat in a chair pointed away from her table. He walked over and sat on her lap. Mr. Edwards stared, astonished. The woman's hand went up and around Mr. Johnson's shoulder. "I love it!" Mr. Edwards said. "I knew Cort had this in him." A short while later, Mr. Johnson reported back to his tutor, grinning, and with the woman's phone number. Though he was a friend for hire, Mr. Edwards's enthusiasm seemed real when he slapped Mr. Johnson's back and shouted, "Good job!"
If you're not ready to go full-time, consider freelancing to try things on for size. Surely there must be someone in your office you could approach today offering your services, unsolicited? Let them know that you couldn't help but notice they don't do so well with the ladies and take it from there.