G Force

Flying with the Wingman

(Aram Boghosian for The Boston Globe)
By Christine Liu
Globe Correspondent / June 9, 2011

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Thomas Edwards Jr. figures out why you can’t seem to get a second date. Why that job seems unattainable. How to get out of a rut. How to break through those stubborn, habitual, mental barriers. He’s a bastion of tough-love analysis, of self-help books, of personal change, of psychological breakthroughs and confidence. He sincerely proffers both platitudes (“No one knows what success is like without failure first’’) and actual advice (“I believe in calling and not texting, it separates you from the pack.’’)

How Edwards morphed into the Professional Wingman is an extensive history worth dissecting over another round of drinks, starting with a traumatic breakup in college, to an obsession with self improvement (prompted by Stephen Covey’s “The Seven Habits of Highly Effective People’’), to unchecked cockiness, a downward-spiraling crash, and, he says, a thoughtful rebuilding of self. Fast forward to the birth of his business in Austin, Texas, during SXSW 2009, when a voice called out through the haze of a bar: “Dude, can you be my wingman?’’ That’s when it clicked for Edwards that he could be that guy. He registered that very night.

In the two years since launching Wingman, Edwards has coaxed confidence from 200 clients, a far-flung crew scattered around the globe from North Carolina to California to Costa Rica — with Boston (he grew up in Hyde Park) and New York City (where he currently resides) making up the bulk of his business. His Wingman services include both one-on-one goal-setting appointments, and in-the-field, let’s-put-those-skills-to-work-in-a-bar nights out.

“You never know when I’m coaching,’’ says Edwards, who keeps his client roster completely confidential. “I pay attention to what they’re doing and make sure they’re feeling good about their progress, wherever they are.’’

Hiring the Wingman isn’t cheap: $140 a month for remote coaching over phone and e-mail, $125 per hour for real-time services, and $900 for a two-day immersion program to “jump-start’’ your dating life. He also provides a fair amount of free content on his website, including video clips on topics ranging from “how to start a conversation at the crosswalk’’ or “how to dress your age.’’ You can even chase him on Foursquare; Edwards designed a personal scavenger hunt of sorts in Austin for SXSW 2011 — winners could snag free Wingman services.

The 800-pound gorilla in the room: Is Edwards single?

“There was a period of time when I was single by choice because there wasn’t a person that blew me away,’’ he says, admitting that he lost credibility for a spell as a dating coach without, well, a date. But in October 2009, once he fell for Laurie Davis (fittingly, an online dating guru who founded eFlirt Expert), Edwards knew it was worth the wait.

“We met on Twitter,’’ Edwards says, launching into the story of their courtship. He pauses for a moment and makes a request: “Make sure you let her know I love her in your article.’’

Wish granted, Wingman.

Interview has been edited and condensed. Christine Liu can be reached at

Thomas Edwards Jr.
“I like to call myself a strategist,’’ says Thomas Edwards Jr., reaching for a bourbon cocktail with gentlemanly ease. “Life’s a strategy, and you gotta win. My job is to find the strategy for you and how to execute it.’’ With an infectious grin and a stylish wardrobe of tailored shirts and jeans, Edwards, 25, has dubbed himself the Professional Wingman, specializing in dating for men and women. But he says he really acts as a motivator for “personal development.’’