The Professional Wingman Backs Singles Up With Confidence Boosting Dating Programs

Men's Dating

The Professional Wingman™ Backs 12,000+ Singles Up With Confidence-Boosting Dating Programs

Hayley Matthews

Written by: Hayley Matthews

Hayley Matthews

Hayley has over 10 years of experience overseeing content strategy, social media engagement, and article opportunities. She has also written hundreds of informational and entertaining blog posts. Her work has appeared in numerous publications, including Bustle, Cosmo, the Huffington Post, AskMen, and Entrepreneur. When she's not writing about dating news, relationship advice, or her fantasy love affair with Leonardo DiCaprio, she enjoys listening to The Beatles, watching Harry Potter reruns, and drinking IPAs.

See full bio »

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

Discuss This! Discuss This!
Advertiser Disclosure

The Short Version: The Professional Wingman team gives singles step-by-step instructions and real-time feedback so they can successfully navigate any dating scenario. Founded by dating expert Thomas Edwards, the company’s one-to-one dating consultations focus on honing interpersonal skills and increasing confidence levels for the long haul. The NYC-based team has over 30,000 collective hours of working with singles, so they can quickly break down what’s keeping you from your happily ever after. Additionally, The Professional Wingman’s flagship online program condenses years of dating experience into an eight-week course that prepares single men to go out and date on their own. If you don’t know what to say or how to act to attract your crush, you should check out The Professional Wingman’s online and in-person coaching lessons to get your dating game up to speed.//

In 2009, Thomas Edwards traveled with a friend to Texas for a weekend festival. They were shooting pool one night when his friend spotted an attractive woman having a drink at the bar. He asked Thomas for help landing the date. If he could pull it off, his friend said, he would buy Thomas free drinks all weekend.

Photo of Thomas Edwards, Founder of The Professional Wingman

Thomas Edwards founded The Professional Wingman to teach valuable dating skills to singles.

Thomas took on the challenge and went with his friend to chat the girl up. The next day, Thomas got a text from his friend saying he’d just gone on a lunch date with the girl from the bar and had had an amazing time. Thomas was thrilled and not just because of the free drinks. He felt gratified that he could use his social prowess to help his friend make a promising connection.

Once Thomas got a glimpse of the good he could do for single guys (and gals), he was hooked and embarked on a career as a dating consultant. He launched a business called The Professional Wingman in Boston and began sharing his advice on body language, conversation topics, and other interpersonal skills relevant to active daters.

Today, his team has worked with over 12,000 singles from all walks of life. Working with these experts helps daters feel more confident and at ease in social settings. The Professional Wingman team gives direct and honest advice to single men and women to empower them to meet and flirt with people.

Thomas’ insight as a coach, wingman, and dating expert is grounded in his own experiences going through the trials and tribulations of dating. “I would call myself my first client,” he told us. “I started with working on myself until I felt comfortable helping others get where they want to be in the dating scene.”

How One-on-One Coaching Helps People Overcome Dating Fears

The Professional Wingman provides one-on-one coaching for men and for women in the dating world. About 70% of the team’s clients are men and 30% are women. The team interviews everyone who applies to make sure they’re dating for the right reasons and can be helped by the program. The average age range of clients is 22 to 44 years old, though it can vary widely — the youngest client Thomas has worked with was 17 and the oldest was 65.

Photo of a coaching session with The Professional Wingman

The Professional Wingman’s personalized dating assistance has benefited over 12,000 singles.

“It’s cool working with such a wide range of people,” Thomas said. “It just goes to show that no one is immune to difficulty in dating.”

The team invests a lot of time and energy into pinpointing a client’s specific dating weaknesses and areas where there’s room for improvement. With a proactive and positive mindset, savvy dating experts let singles know what they can do to get fast results in the dating scene. It’s not about pickup lines for them; it’s about fostering genuine conversations and showing sincere interest.

The goal of The Professional Wingman is to prepare clients to attract dates without someone standing beside them the entire time. “There’s more value in teaching people to do it on their own,” Thomas said. Whether you’re newly graduated from college and looking to settle down or recently divorced and hoping to learn to date again, The Professional Wingman can help you regain your footing and find your stride.

A New 8-Week Program For Men Motivates Lasting Changes

Just like the dating arena, The Professional Wingman’s business never stands still. Thomas is continually brainstorming how he can better equip modern singles to attract quality partners. His most recent innovation is a new eight-week coaching program designed specifically for single men.

Photo of The Professional Wingman logo

The Professional Wingman’s online course puts single men through their paces in an eight-week dating boot camp.

This flagship program will be the center of The Professional Wingman’s services going forward. Thomas said his goal is to create a workshop atmosphere that teaches the same lessons of his coaching sessions but on a larger scale.

Now anyone anywhere in the world can sign up to learn from this team of dating experts. The online program has become an incredibly popular and effective resource for single men.

“We’ve tested it, we’ve tried it, we’ve proven it, and we’ve gotten results from it,” Thomas said. “You learn all the strategies, and we as a team give you support along the way.”

For every module, participants get Action Items to take into the real world and practice on their own time. These assignments could be something as simple as joining a local club or meetup. Dating coaches provide guided advice and feedback throughout the eight-week course and hold singles accountable for carrying out those lessons in real-life situations.

“There’s no excuse in terms of you not having opportunities to meet people,” Thomas said. “We show you where to go so you can use the strategies that we teach you to not only meet new people but connect with them.”

Boasting a 50% Relationship Rate & 150+ Marriages

Over the past eight years, The Professional Wingman has consulted with hundreds of single men and women, about half of whom have gone on to enjoy long-term relationships. So far, the company’s client marriage count is above 150, and dozens of children are alive today because of The Professional Wingman’s work with singles.

Sometimes clients come to The Professional Wingman because they’re seeking a long-term relationship and other times they just need a way into the social scene. The dating consultants work with singles to increase their confidence and help them reach their goals.

“We’ve spent well over 30,000 hours and over eight years watching and interacting with women, including thousands of hours of coaching in different social environments.” — The Professional Wingman website

One client had a social disorder that inhibited him from understanding the nuances of the dating world. Thomas took him under his wing and put him through a few dating simulations to give feedback on how he could improve. Over time, the client improved his social skills and is now married and has a young daughter.

Another 42-year-old single was a good-looking Southern gentleman but still a virgin because he struggled with anxiety issues. After working with The Professional Wingman for two years, he overcame his fears and met the woman of his dreams. He’d never gotten past the first date before, but now he’s in a committed relationship with someone who adores him.

Thomas told us the transformation is always exciting to see. “I’m in the trenches with these guys,” Thomas said, “so they often become good friends, and I get to go to their weddings, meet their kids, and see them progress.”

“Thomas has been there,” wrote Tim Stiffler-Dean, a former client from Dayton, Ohio. “I look forward to someday introducing him to my wife and saying ‘This is the guy who helped me become the man I am today.'”

The Professional Wingman frequently receives positive feedback from singles who found love after taking the dating coaching lessons to heart. One client even gave his son the middle name Thomas to honor the impact the dating consultant had in his life and happiness.

That kind of gesture is mind-blowing to Thomas. “I’m grateful to be somebody who’s able to help people make lasting changes in their lives,” he told us. “I want to keep that going as long as I can.”

The Professional Wingman: Actionable Advice For Modern Daters

Not everyone feels comfortable approaching a stranger and building a relationship from scratch, but that’s Thomas’ bread and butter. Years ago, when he helped his friend pick up a date at a bar, he realized he could have a meaningful impact on the happiness of love-oriented singles worldwide. And that’s what he’s done.

Thomas’ support as a savvy conversationalist and confidence-boosting wingman has aided thousands of daters of all ages. His consultancy company, The Professional Wingman, offers one-on-one coaching and online programs to bolster a person’s dating prospects. The expert team’s hands-on assistance empowers singles to make a friend, land a date, or find love in any social setting.

“I’m always looking for the next opportunity to do our job better or have a wider impact,” Thomas said. “It’s such a fulfilling process, and I’m so happy to help my clients achieve their goals and live the life they wanted but maybe didn’t know how to get there on their own.”

Advertiser Disclosure is a free online resource that offers valuable content and comparison services to users. To keep this resource 100% free, we receive compensation from many of the offers listed on the site. Along with key review factors, this compensation may impact how and where products appear across the site (including, for example, the order in which they appear). does not include the entire universe of available offers. Editorial opinions expressed on the site are strictly our own and are not provided, endorsed, or approved by advertisers.

Our Editorial Review Policy

Our site is committed to publishing independent, accurate content guided by strict editorial guidelines. Before articles and reviews are published on our site, they undergo a thorough review process performed by a team of independent editors and subject-matter experts to ensure the content’s accuracy, timeliness, and impartiality. Our editorial team is separate and independent of our site’s advertisers, and the opinions they express on our site are their own. To read more about our team members and their editorial backgrounds, please visit our site’s About page.