The other day, I was catching up with an old friend who I had met during his stint in NYC for a study abroad program. The circumstances of how we met and became friends was really a matter of timing and the phases of life we were both in at the time as single, curious, and socially awkward men trying to understand the dating game.
Fast forward seven years later, despite all the changes that had happened during that time, we instantly reconnected. As we talked and shared what we’ve been up to in our lives, we started laughing and reminiscing about the ridiculous escapades we had gotten into when he was living here in NYC.
My old friend Mick is the polar opposite of me. Ethnically he’s Indian, is as British as a Full English Breakfast, and has a thick London drawl. He’s also naturally handsome, charming, has a great fashion sense, and is armed with a quick wit that would make you think he was the Indian incarnation of Russell Brand. Regardless of our personality differences, we always fed off each other’s energy. A night out on the town with him was always a blast.
After close to a decade of being a student of the dating game, coaching in one of the toughest nightlife cities in the world, and experiencing the peaks and valleys of hookup culture, these days it’s hard for me to find much joy in going out into the nightlife, even when I’m off the clock and out with my friends and meeting women.
You probably didn’t come here to read a narrative of me venting about the realities of being a dating coach, but hear me out for a moment. Going back to my friend Mick, it’s amazing what time, distance, and life experience can do to someone you haven’t seen in ages. The passage of time is something we all take for granted. Being so embroiled in our day-to-day worries, we sometimes don’t realize how much we and the people around us change.
After seeing him for the first time in seven years, I could tell that Mick was a changed man. While he was still handsome, witty, and fashionable, I sensed something different about his demeanor. He was calmer, self-aware, mature, and mellow. During his visit, he also asked me to be one of the groomsmen for his wedding next summer. I felt honored and humbled that he asked me to be part of his big day.
The biggest surprise to me was him getting engaged. When we first met, we were in our early 20s, transitioning out of our awkward teenage years and entering the unpredictable period of young adulthood. At the time, we were in the early stages of learning about dating and seduction. Let’s just say that period was filled with a lot of weird nights, lots of firsts like a first kiss, first one night stand, first time getting ghosted, first awkward dates, etc.
Mick, being the crazier one out of the two of us, had a lot more success early on than I did. He once proclaimed to me during that period that he would never get hitched, would become a writer, and would live the playboy lifestyle for the rest of his worldly existence.
That night, while we were catching up on the last seven years and sharing our personal triumphs and struggles, I asked him, “Mick, what happened? You once told me you would never give up the player lifestyle. What brought out this change?” He simply told me, “It all started when you asked me before I left New York all those years ago… ‘What exactly do you want out of this?’”
I always ask my students this same question at various points during our Dating Mastery Program. As a coach, it’s a way for me to gauge and understand them and their personal motivations so I can tailor the program to help them achieve their goals. But it’s also become a coaching tool to help my students discover their own personal motivations and develop more self-awareness.
My friend Mick had thought deeply about his own wants and needs after returning to London. He came to the conclusion that after two years abroad with a lot of wacky experiences and notches under his belt, he started to feel empty and unfulfilled by the meaningless chase of casual sex and short-term relationships that never really amounted to much.
Serial dating isn’t all it’s chalked up to be.
Mick’s story is actually quite common in my line of work. He had to go through that brief crazy period of “sowing his oats,” as that old English saying goes, to really discover what was important to him and to find a partner he could build and nurture a healthy relationship with. It’s part of every man’s journey as he goes through the stages of life. But I’m not saying that dating needs to be about racking up notches under your belt like a video game.
While our students come from diverse backgrounds with pages of life experience that could probably fill a whole library, if we were to narrow down the reasons why they take our classes, it’s always either to learn the fundamentals of courtship in order to get a girlfriend and eventually get married, or explore their curiosities and become serial daters (which is getting less common post-pandemic).
There was a point in my life where I used to take pride in being a serial dater. I had felt a lot of inadequacy for being so awkward and incompetent with women when I was going through puberty and high school and early college. I hate to admit it now, but I fell down the serial dater rabbit hole to make up for all those years of feeling awkward and inadequate.
To make a long story short, much like my friend Mick, it led to a period of apathy and nihilism when I continued on that unhealthy trajectory. I empathize with a lot of young men out there, since this is a pretty toxic narrative that’s often pushed around masculinity and what you need to do to lead a fulfilling life and be considered worthy.
A common belief that a lot of men have when first learning courtship and seduction is the need to rack up a “kill count,” which is a colloquial term for sleeping with as many women as possible in order to build a masculine identity and feel worthy as a man.
As I say to every student who comes through our classes, besides “What do you want out of this?” I also make it a point to tell them: “Your identity as a man is not based on the perception of your success with women. You’re more than that and while this is something you’re struggling with right now, even after you get better with women, it’s important to remember and also understand that you’re a human being with flaws, aspirations, and struggles like everyone else. There’s more to life than fulfilling your teenage fantasy of sowing your oats.”
I can tell you from experience that it’s empty and unfulfilling to constantly date with impunity and without building a healthy foundation with depth, emotional connection, and compatibility. As I’ve gotten older, I’ve come to realize that while you can explain something to someone and give the best possible advice, sometimes that person has to go through the actual experiences and the highs and lows to really understand it.
For every young man reading this article, I want to leave you with a few key pieces of advice that will hopefully save you from a lot of heartache and apathy, and to actually date with a purpose.
What do you want out of this?
In the first week of our Dating Mastery Program and other workshops, we have our students lay out their goals for the class and beyond. This not only gives us insight on where they’re at, but it’s a means for them to be able to visualize and have a metric to hold themselves accountable to during and after the program.
At any stage in your dating life, you always have to ask yourself:
- Where am I at?
- What do I want?
- What are the steps I need to take to get there?
The more specific you get, the more likely you are to figure out what’s important to you, and the more likely you are to succeed at achieving that specific goal.
I’m not talking about superficial metrics like the amount of women you approach, how many dates you go on, or how many times you close the deal on the first date. I’m talking about long-term goals like building a relationship, finding a partner you have good chemistry and compatibility with, figuring out your values and boundaries, and getting married and starting a family if that’s important to you.
Success means different things to different people, and it’s important to clarify this early on so you have a baseline. That doesn’t mean these goals and metrics won’t evolve as you do. Even with all my failures and successes in the dating game, I still go through this exercise every few years, and my goals continue to change over time. Also, this doesn’t just apply to dating; it can apply to any area of life you feel stuck in.
Quality vs. Quantity
I don’t keep track of the women I’ve successfully dated, had a quick fling with, or the amount of times I’ve gotten laid. In fact, since I first learned dating and seduction, I’ve become more selective and sexually conservative.
Over the years, I’ve come across a lot of dating “experts” who focus on the quantity of women they’ve successfully closed the deal with. They often shame men who don’t focus on the numbers. Or they use it as a cheesy marketing tactic to sell their products and services.
Some were legitimate, but a lot of them were just wanna-be Lotharios with embellished stories to not only sell their programs, but also feel more secure in their own identity as a man. My point is, you don’t have to approach or try to date every single woman who catches your eye.
While in some ways it’s psychologically easier to gamify dating and try to hit an arbitrary metric like how many women you approach or how many dates go on, let’s be real. It’s unrealistic, unhealthy, and unnecessary to approach and treat every single girl you meet or see as a potential sales lead.
Yes, dating is a numbers game. A lot of it is based on circumstance, timing, intimacy, and other factors out of our control. I’m not saying you shouldn’t practice your social and dating skills. All I’m saying is that you don’t need to make it the center of your life or put unnecessary pressure on yourself in order to feel validated.
I had to learn the hard way and eventually come to terms with this when I got into my late 20s and other more important things in my life started to take precedence. Things such as my entrepreneurial career, academics, and dealing with personal demons made me realize that there’s more to life than trying to find my sense of masculinity in every woman that I meet or see.
You don’t have to go out with or sleep with every woman you cross paths with to feel validated as a man. Going back to the first point, figure out what’s important to you, what your values are, and what you’re genuinely attracted to.
By doing this, you can get more specific and focus on building a life that’s going to attract you to the right women and eventually the right partner. Focus on quality, and don’t be afraid to say no and walk away from someone if they’re not your type. If you need a starting point on the steps and structure to build that kind of lifestyle, check out our article on dating in your 20s.
A woman doesn’t define your identity or masculinity, you do.
My uncle gave me this piece of advice when we were away on our family vacation this past summer: “Rob, don’t try to find yourself in another woman. A girlfriend is supposed to be a fun addition and support to your life, not the definition of it.”
While I had heard this advice many times throughout my teens and 20s, I really needed to hear it again, especially after he saw how down and somber I was feeling at the time after a relationship that I was nurturing with a girl ended up fizzling out due to external circumstances that were out of our control.
Meeting women, dating, and eventually finding a girlfriend can be both a daunting and exhilarating process. The feeling and intimacy of loving someone and being loved and wanted can be intoxicating. There’s nothing wrong with wanting a girlfriend and a healthy relationship. But oftentimes, and I’ve seen this in both myself and with our students over the years, we end up losing ourselves and our identity when we’re chasing women or getting into relationships in order to feel masculine and validated.
Throughout my time in the dating scene, I’ve come to learn that while we unconsciously look to validate our masculinity based on our success with women, as a man with a purpose, remember that you’re more than that and meeting the right girl is just a bonus.
This video really helped me understand and articulate some of the issues that I ran into as a young adult and the common identity issues that the men who take our workshops try to navigate through.
In a nutshell, a relationship doesn’t define you. A woman should be a positive addition to your life, not the center of it.
Here’s a quick recap of the concepts we covered in this article. If you want to date with purpose and intention, you must ask and remind yourself:
- What do you want out of this?
- Know that you don’t have to go for every girl you see. Focus on quality over quantity and only date women you’re genuinely attracted to and have compatibility and commonalities with.
- A woman or a relationship doesn’t define your identity or masculinity, you do.
‘Til next time,