Here's Thomas' Story.

Whenever I meet people and tell them, "I'm a Professional Wingman," most are surprised and instantly respond by asking, “how did you get into that?” If you’re one of those wondering, keep reading and you’ll find out how this all happened.

It Begins With Me Already Finding The One.

I was a sophomore in college and was dating my girlfriend for over two years – she was awesome. Being a hopeless romantic and huge monogamist, I always wanted to be in a relationship, even though I couldn’t really get into one. But this was it. I finally found The One and she was an amazing person. I went as far as asking her parents for their blessing, which they gave to me. So, clearly it was serious. And even though I was 19, I thought I knew what I wanted.

A week later, I got a phone call from my girlfriend, thinking we were going to talk about her staying at my place for the weekend. But this call was different. She sounded weird and I didn’t know why. Eventually, she came out and told me she cheated on me with some random dude she met in her class.

I Was Totally Crushed and Thought My Entire Life Was Over.

Everything that I had planned for my life was up in smoke. I couldn’t talk to her anymore at that point so I hung up the phone and to avoid any of my roommates hearing me, I went into the bathroom, turned on the shower and cried for 30 minutes. My identity, as I saw it, was completely lost.

After my crying shower, I went into what could only be described as a quarter-life crisis. I transferred to a different school, moved off campus, got an apartment with 5 other guys, even bought a car, got a job to pay for the car — anything that could change my identity from what it was before. But all of those materialistic things didn’t amount to anything so I did a little more soul searching. One day, I came across a book called Seven Habits of Highly Effective People by Stephen Covey and it changed my life. I began to understand the standards I needed to uphold for myself and others. It helped me change how I should be interacting and communicating with people and the goals I wanted to accomplish.

As an aside, if you haven’t read the book, I strongly recommend it. It’s a book I try to read once a year to give myself a refresh.

It’s so important to understand the values that are tied to the book and one thing that stood out at that time in my life was the concept of being independent and interdependent. Interdependence was something I never even knew existed.

That level of interdependence Covey talks about is one where it’s no longer just about you. It’s about collaborating with others for a greater good. I could go deeper but you should read the book to really understand it all. Anyway, the concept just blew my mind in terms of how I wanted to interact with people in general, not just in my romantic relationships.

I Got Addicted to the "Knowledge High" of Personal Development.

As you can tell, it really was a point of inflection in my life and I really got addicted to the idea of personal development. So I did a ton of reading and read books on communication, fitness, nutrition, fashion, style, sex, relationships, networking, test taking, interviewing, public speaking — anything that I could get my hands on that I thought was going to be effective and beneficial for my life. My brain was a sponge for the next two and a half years.

All the while I was reading, I wasn’t doing much practical work on myself but being at this new school, I figured I had a clean slate. No one knew me there and I didn’t have anything to lose. So I started to practice the things I learned through my reading and once I started to see some results, I committed and went all in.


Within a Year and a Half, I’m a Senior in College and Living the Life of a Rockstar. 

I had my own place, was an RA (Resident Assistant), involved in athletics, campus activities, and my fraternity. I became very popular on campus and during this time, professors loved me, I had a lot of great friends, and most importantly, women LOVED me. It was just like everything I dreamed of. At the time, I was single by choice and a relationship wasn’t something I was looking for because I wanted to focus on really developing myself until I reached a point of interdependence — sharing the life I created for myself with someone special. And eventually, that happened.

When I Met Her, She Was the Hottest Girl I Ever Dated at That Point.

Within three weeks of meeting her, we were dating. Once I “got her,” I thought that was the last piece of the puzzle for the perfect life. If there was a checklist, I was able to check every item off, having accomplished everything I wanted to do. But there was a lesson I soon had to learn — it’s harder to stay on top than it is to get to the top.

Since I thought I “did it all,” I got very cocky and complacent with my “success” and all the things I did to get to where I was, I stopped doing. I skipped class, thinking my professors would just let me slide and workouts because I didn’t need to stay in shape anymore. I neglected my friends because I wanted to hang with my hot girlfriend and when I got to hang with her, I wasn’t trying as hard to keep her attracted to me. Why would I? I already had her, right? What was the point? In other words, I reverted back to my old self.

A few months later, I got a call from my girlfriend during spring and she said something along the lines of,

Thomas, you’re not the same guy I started dating a few months back and this was not what I signed up for. I don’t think there’s anything else in this relationship that I can personally get out of — we’re done.

Once Again, Completely Crushed.

While it was very mature of her, I didn’t see that at the time. This time, for the worst, knowing that I spent years trying to create the life I wanted and I pissed it all away in a matter of a few months. I invested so much into that relationship — or so i thought — that I lost myself and my identity again. So I was back to square one. My downward spiral began and my life fell apart. I had to leave my RA position because I couldn’t handle the responsibility and stress, I still wasn’t going to class because I was afraid to run into her on campus and face the shame. Eventually, it led me to not even going to the cafeteria in order to avoid seeing her and I stopped taking care of myself. One weekend, I got really sick — like, “probably should have gone to the hospital” sick. Realizing that I didn’t have anyone to call to take care of me because I neglected everyone was the lowest point of my life. Eventually, I called the one person who I knew would answer.

I Called My Mum.

Sobbing, I talked with her and she suggested I go back to live with her and my dad and start my life over. I didn’t really like the idea of living with my parents after college, but it was my only safe haven and opportunity to start fresh. I thought I needed to become a certain type of guy to get the life and the girl I wanted but never really took the time to understand who I truly was. That was my chance. And I needed to find a way to hold myself accountable so I didn’t take things for granted and throw it all away like I did before.

A Completely New Accountability System.

That was when I decided to start a blog as my accountability system. I figured if this stuff was online then it was permanent. People will read it and that alone will force me to be accountable. I blogged about life back in Boston, my lifestyle, looking for a job in video games, my "wine" diet, and so much more. At the time, I was working in hotels and had the evening shift (working from 3-11PM). When I got off work, I wanted to hang with friends but when I texted them, they’d reply saying they were about to go to bed and it was too late to go out. It was at this point, I realized I had to create a second social circle of friends I could hang out with, given my work schedule. This brought me to think about how I had to restart my life after my ex cheated on me. That moment inspired me to take that time to really understand myself and create the kind of life that was fit for me and my personality, not what I thought was going to get the kind of women I wanted.

30 Bars in 30 Nights.

My blog was geared towards that and my first experiment was what I called “30 in 30.” This experiment pushed me to go to 30 bars for 30 consecutive nights. Needless to say, I had many lonely nights but anytime I went to the bar, I had just one objective. I’d go, chat up the bartender, order a drink, and whoever I sat or stood next to, I’d chat up. It didn’t matter if it was a guy or girl, I just wanted to get comfortable talking to random people. It was certainly a struggle as many interactions didn’t pan out well but I eventually became more comfortable putting myself out there and I ended up having great interactions with people who soon later became my friends.


Documenting this process was something my readers really enjoyed so my anonymous blog focused on my lifestyle. Then as my social life started to take off, so did my dating life. I eventually started to meet really awesome women, my interactions with them felt a lot easier, and I was fascinated in finding out why. My blog was the perfect platform to chronicle this development.

Well, my tipping point (cue Malcolm Gladwell) was when I got into a relationship with someone who was 19 years older than me. I was 23 at the time, she was 42 and when I blogged about my experience, my readers resonated with that. It was surprising to see how many people were really drawn to that particular experience. Many readers said, 

“As a 23 year old, the fact you are able to not only engage someone whose that much older than you but to sustain a relationship, you must have some innate wisdom or are an old soul in a young body.”

That was the beginning of my credibility that would allow people to ask me for advice based on my experiences.

How I Got My "First" Client.

As I began giving advice, I eventually ended up meeting a guy through an online personal development forum who wanted me to mentor him. He was 39, from Chicago, just got a divorce, and we strictly communicated through email. He wanted me to help him recover from his divorce and even though I had NO idea how to relate to his divorce, I could relate to the fact that I knew what it was like to start over from scratch. Through that bond and our work together, he was able to turn things around. He started his own business, reconnected with his college buddies, even went sky diving for the first time, and eventually began dating again.

Having helped someone through that experience made me realize my passion is helping others not go through the same process that I did. I never had someone I could have gone to for finding out what I was doing wrong or what I should have done and I wanted to be that person for other people. Little did I know I would have had my biggest opportunity only a few months later.

What Happened Next Changed My Life – and Soon, Many Others.

Inspired by a friend, I decided to go to South by Southwest, an interactive conference in Austin, Texas, to try to discover a way to monetize my passion for personal development. I was meeting so many people, looking for that idea, not knowing that the idea would hit me at a place where my own journey began — the bar.


While I was with good buddy of mine, he saw a really gorgeous woman at the bar and wanted me go over there, chat her up, and then introduce them so they could go out on a date. I thought he was joking until he offered to pay for my drinks for the rest of the weekend.  So I walked over, chatted her up, introduced them and “went to the bathroom.” When I came back, I saw him getting her number and the following day, he texted me saying he had a great lunch date with her and to let him know where I was that night because drinks were on him, ending the text with, “thanks for being my wingman.” 

And that was when it hit me. It’s one thing to facilitate introductions but I knew there was value in teaching others how to do it on their own. I loved that he called me a wingman so, like an athlete, I figured it'd be cool to “go pro” and become a professional wingman. That was the moment The Professional Wingman® was born.

And to this day, my mission is the same. I want people to know they can trust someone who’s been where they’ve been, in making sure they don’t have to be alone on this journey, and what took me several years to figure out can take them much less time with my fresh, authentic perspective and guidance.

So how did my love life turn out? Well, let's just say that I actually have found "The One." Being married to the most awesome woman in the world makes me proud to say that I'm a true product of my own service. The New York Times ended up doing a wedding feature on our "love story" in the video below.


Now that you know my story, I think it’s time for you to tell me yours. Click the button below and let’s get started. Hope to hear from you soon!