During my early 20s I wasn’t too happy with my love life. Then I discovered the dating advice industry. I started working on my social skills and occasionally talking to the women that crossed my path. But even after many years of self-improvement I still wasn’t connecting with the kinds of girls I liked the most and rarely had a girlfriend. So at some point I decided to treat the matter with more urgency and ramp up my efforts: During 2020 I approached virtually every attractive woman I saw – every time of the day and everywhere I went. I also built an app to monitor my progress and keep me motivated through the storm of rejections I was receiving. In this highly personal essay, I explain what that episode taught me and how it ultimately led me to a loving monogamous relationship.

When I contracted Chlamydia for the second time, my doctor asked me how many sexual partners I had had during the past year. I knew the exact number because I had started to keep a precise digital account of my dating life. But I didn’t want to seem weird. So I closed my eyes and made some counting noises. I rounded it down and told him. There was a break. He looked at me and said: “Oh. Are you OK?”

I wasn’t sure if I was OK. At 30 years of age, I had just recently learned to express my sexuality after a celibate and somewhat repressed youth. I had discovered that I could in fact be an attractive and charming man, even without drugs and alcohol. And I had invested a lot of time in building my confidence around women and learning to flirt. Now, I was reaping the fruits.

I didn’t use online dating, because it never worked well for me. But with the help of the game community I had learned that you could just as well meet single women in the real world: On the weekend I mingled with the crowds at parks, bars and clubs. And during the week I wandered across Main Street – often together with other men on a similar mission – or just kept my eyes open during my daily commute to work. When I saw a gorgeous face or even just a beautiful silhouette somewhere (this happens around 3 times on an average walk through my city), I would go up to her, make a compliment and try to start a conversation.

Initially the results were meagre. Flirting made me nervous and anxious. With the hottest girls, I usually got blown out in a matter of seconds. Sometimes I managed to stumble my way to an actual conversation, but when I did get a phone number they usually didn’t respond. Every once in a while there was a match, but they were mostly short-lived so I remained single and free to keep looking.

I was raised outside of mainstream culture and always felt different and special. I couldn’t relate to the lifestyle of most young people around me and found much of it straight-up ridiculous. I seemed “weird” in their eyes, too, so the feeling was mutual. It didn’t surprise me that it would be hard for me to find a person who understood and liked my quirks, someone I could actually be in a committed long-term relationship with.

However, the quality of my life depended critically on finding that rare, compatible partner. I liked myself the way I was and couldn’t imagine compromising my character for someone else. Of course, I also didn’t like the thought of being a bachelor forever. So I had to cast a wide net and put in my best effort. If the sample size was big enough, there surely would be someone who was weird in the same or in a compatible way. There are plenty of weird (and hot) people in a city like Berlin, so I was confident that I would find her someday. After all, any one of these strangers could be the woman of my dreams – why limit myself to my friends circle or the tinder algorithm or the Indian girls whose CVs my mother sent me on WhatsApp every now and then? I would rather stay on the hunt, jerk off and be a bit lonely, than being stuck with an incompatible partner out of laziness and fear of venturing out into the unknown.

Honestly, I even started to enjoy the process. It was exciting to walk through a city and see every moment as an opportunity to create a new passionate connection or at least a spontaneous adventure. I took great pride in being able to talk to almost any girl in any situation (at least for 2 seconds). The very real risk of being publicly rejected and humiliated gave me an adrenalin kick. Facing rejection in the real world became an almost spiritual experience. At any rate, it was more fun than the kind of rejection I had gotten on dating apps: an empty inbox. Every hard-blow face-to-face rejection reminded me of my special identity and strengthened the belief that I was different from the masses. Every rejection taught me a little bit about the social dynamics between men and women. Every rejection gave me an opportunity to build even more courage and strengthen my mental frame.

Given this fascination with rejection, I was drawn to the more difficult approach settings: When I saw a girl surrounded by her friends, shopping with her mum or dressed up to appear totally out of my league, that inner voice became especially loud and clear: “Go! Overcome your fear!” With practice I got better at discerning the dynamics and maneuvering through the conversation. Soon, I was able to get a few phone numbers on my social afternoon walks, an instant coffee date with a woman I had just met and a good chance of having a beautiful companion for a night or two. It was exciting.

When I turned 30, however, I noticed a problematic pattern: I was dating a lot, but rarely managed to get into the deeper end of a relationship. After spending a few evenings together, I would always find something that put me off: her habits, her political views, the way she made or didn’t make her bed, the chemistry of her body, heck, sometimes it was just the way she laughed that annoyed me enough to move on. Knowing that a new adventure was just a few approaches away, I always thought I could do better. Well, this went on for years. And it cost a lot of time and energy. My dating schedule was jeopardizing my career and entrepreneurial pursuits! Yes, partner choice was important to me – but I also still had other things to do in life. My strategy of casting a wide net and waiting for the big fish wasn’t quite working. I had ended up with tons of small fish and my hands full.

I decided to make 3 major changes: 

First, I started tracking and analyzing my efforts. Until that point I had only gone out occasionally when I was in the mood for it. In order to build momentum and really get better at finding and attracting the girls I was into, I had to start going out more consistently and systematically. I set myself a clear goal: I would approach 20 women every week, no matter what. I wanted to keep track of this weekly count and out of dissatisfaction with existing solutions, I built a smartphone application for that exact purpose. This app also allowed me to take a quick note after each approach to remember what I had talked about with the girl and reflect on what I could have done better. I followed the discipline religiously. Having that count always visible on my phone reminded me that I had an important task to perform each week. It helped me stay motivated even when I had plenty of other things to do and could have easily made up an excuse to not go out. And thus, in that momentous year of 2020, I ended up meeting 631 women and going on 119 dates. Correct: On average 2 new encounters every day and 3 dates every week – each with a small reflection on how it went.

The second change I made was that I signed up for the paid programs of some of the dating experts I had found on the internet. Previous to that, I had only consumed free YouTube videos and maintained a cynical skepticism towards the sketchy business models of the self-help industry. After learning more, however, I found coaches that resonated with me and whom I could trust despite the social stigma on mainstream media. I paid them for premium content, weekend bootcamps and even personal one-on-one coachings. This was a big step that I had been trying to avoid. It was hard to admit to myself that I needed help so much that I would turn to these generally despised figures, decried by many as pickup artists. And it was hard to admit to my friends that I liked some of the ideas of those people and didn’t think that pickup was a bad thing per se. In the obscurity of the internet I could maintain the lie that I was just an observer of this industry and not a part of it. But if I physically traveled to a city to attend a seminar, I really couldn’t stay in the closet anymore. I lost a few of my best friends over this.

But it was worth it. The coaches pushed me to do more intense introspection and get explicit about what I really wanted in life. At their recommendation, I spent an entire weekend locked in a chamber to write down all my character traits, strengths, beliefs, and goals in painstaking detail. I also wrote down a long list with specific characteristics I desired in my ideal partner. Having that inner clarity and a well-defined target persona helped immensely in attracting more of the right kind of people.

The third fundamental change I undertook was that I looked more closely at my own emotions. Up until that point, I had never taken the time to really understand what emotions are, why they matter and how one can influence them. I read a somewhat esoteric book on the subject. It made me realize that I had some subconscious blockages stemming from my childhood. As a boy growing up, my sexuality and emotions had largely been repressed in favor of educational and professional attainment. My addiction to sexual novelty as a young adult was a compensation for that earlier part of my youth. At the same time, the ingrained desire to always excel and get better made it hard for me to accept and embrace a partner with her imperfections. Thus, I was actually unable to experience deep romantic love. I started doing psychological exercises to release those emotional roadblocks. For example, every morning, right after waking up, I wrote the same words on the top of the page in my diary: I allow myself to find the right partner for a loving relationship. When this affirmation stirred up emotions inside of me, instead of ignoring them, I actively listened, allowed them to rush through my body, meditated on them and let them go.

And then it actually happened.

It was a Friday night. The harsh Corona winter of 2020 was about to hit, but a handful of bars and clubs still had permission to operate for the weekend. I had hired a coach and we were going out together. We focused on “night game”, since I had previously identified this as one of my weaknesses. After a theory session at home, we approached a few girls in the street (“where is the party at!?”) and a few more in the queue in front of a club (“let’s wait together!?”). They all talked their way out. But when we entered the club, I sensed her immediately. A gorgeous woman, tall, slim, blonde, sitting alone just a few metres away. The Corona restrictions prescribed that everyone stay seated at their tables, but I went over anyway. It was instinctive. I had done it a million times and I did it again without even thinking: I sat down next to her and introduced myself. The vibe was great and I simply shared what naturally came to my mind. Since the dance floor was closed, I invited her to dance with just our hands. Her friend came back from the bar and she got along with my professional wingman. An hour later we were all at my place. Night game was fast. I could see why “normal” men use clubs and bars to meet girls rather than lurking around the streets by day.

We started seeing each other and this woman stood out. I knew from the start that she was immensely intelligent. I loved her laugh and I loved her touch. And the more I got to know her, the more similarities I found. Certainly there were issues we didn’t agree on, but I could always appreciate her point of view and so these seemed like an opportunity for growth. I even liked her weaknesses. I could relate to them, because many of them were weaknesses that I had overcome myself. Clearly this was one of the hottest girls I had met during all those years of search, but more importantly we shared the same aesthetic taste, intellectual wavelength and fundamental worldviews.

I had been racking up approaches always with this one ultimate goal in mind: When I meet the girl that I want to build a longer term future with, I want to be cool enough to approach and seduce her. Now this had actually happened. But I couldn’t quite believe it. Reaching a goal was supposed to feel like the yellow cyclist crossing the finish line in Paris. I had won the race but I couldn’t stop pedalling. I was still getting better at this dating thing – was it the right time to pull out of the game and commit to a relationship? There could always be a better match around the corner, someone even more perfect… Through years of practice I had conditioned my brain to never pass on such opportunities. And hence, on my walks through the city, I couldn’t hold myself back from still approaching new girls. It always transpired quickly that they couldn’t compare with my girlfriend, so when I went on dates I didn’t find it worth telling her. I became dishonest.

When she found out it became clear that I would lose her over this. She forced me to reflect and think about it deeply:

Achill, man: You cannot possibly meet all the women in the world. So whoever you choose, there will ALWAYS be that possibility of there being a better match for you somewhere out there. But you don’t want to spend your entire life searching, right!? If you keep hunting you will never have the peace of mind to sit down, fully enjoy what you have and focus on your actual life’s mission of creating something valuable for society… At some point you have to make a hard cut and accept someone, embrace their human imperfections, and start growing together. This will always be a tough call. Are you ready?

Statistically, the answer had to be yes. I had met countless women from all walks of life and knew exactly what I liked. I had also found out how few of them liked me! I had followed every hot girl for a year. All of these women were attractive in their own right. But in a decade of perpetual search, the one I was with was by far the most compatible. In all likelihood, the millions of girls I still hadn’t met would be a lot like the thousands I had already met. The sample size was big enough to assert this with a narrow confidence interval. I even looked up more complex mathematical models to analyze my problem (what’s the Bellman equation for this problem?!) – I was still an economist by heart – and the conclusion was the same: The rational thing to do was to commit and be content.

But rational agent theory wasn’t enough to rewire my brain. It took a more visceral force. And that came in the form of a wet dream: I was tricked by my friends into sleeping with a woman who hadn’t been very responsive to my advances. After the climax, I realized that she was actually dead and had been stuffed from the inside with plastic foam. I felt shame and disgust. I felt dead myself, empty and broken. I told my girlfriend about the dream and she helped me crystallize the meaning. I decided that it was a deep symbol for my decision to not want to have sex for its own sake anymore. Sex for its own sake is like sex with a corpse.

The love I had found with my girlfriend was rare and worth protecting and nourishing. It also set free new reserves of energy and boosted my ability to do focused work. In my life, I always look for the hard and uncomfortable path, the path that makes me grow the most. Now, that path was to commit and resist the ever-present temptation of the new. Switching gears and entering this entirely new game took more strength and courage than continuing in my old ways. So it felt noble. And I was able to do it because I had played the other game long enough.

There is a fine balance to be achieved here and I think my story illustrates it well: As a man with limited dating prospects, you want to push yourself, improve your outcomes and find more compatible partners. The dissatisfaction of being single can be a great motivator to get your shit together and become serious about your personal goals. But once you are on that upward trajectory, self-improvement can become addictive and counterproductive. With certain things in life, you cannot push yourself individually forever. Building a long-term partnership means accepting someone else into your team and, from then on, pushing yourself together. If you don’t muster the strength to make that paradigm shift, you can easily end up getting caught in a hamster wheel without any deep relationships. One of the keys to having that strength is to cherish and celebrate the freedom to follow every impulse while you’re single. When it’s time to get hinged, you don’t want to have any regrets and you don’t want to be curious anymore.

Footnotes

• Title photo by Debby Hudson on Unsplash