Approximately six months ago, I decided to start dedicating serious time and attention to dating. For context, last year, I had reflected that after enough changes happened, my life path was now more ready to include someone else than it ever was before, and also that I desired it. To anyone asking, I would easily clarify that I am curious to both experience new things, and re-experience old things, together with another person.

On the topic of how to meet romantic partners: in the fall, I had talked to a friend about it and she had advised that she had approached dating like a part-time job, meeting many people one after another, seriously and over the course of multiple years, until something would “stick”. It took her years and innumerable in-person meetings, yet it eventually worked (for her). This is the input that helped me decide, around December 2025, to follow her example and put myself to work, with an open mind and lots of patience.

After a few months and dozens of encounters, I felt something was off: although I am very successful in meeting new folk for first dates, frequently (thanks to the help and support from a friend more skilled than I was in the art of presenting oneself online), nearly all of them failed to lead to a second date. With just two exceptions, the choice to not pursue further was mine. There was no “click” that made me desire to spend more time together.

Trying to explain the situation to my friends, I shared that every first date was a pleasant moment—I never felt I was uncomfortable or wasting my time, and I was always objectively interested to get to know the other person—yet, nearly everytime, something different caused the final mismatch. In most cases the reason was nondescript, a feeling perhaps that I found my interlocutors insufficiently stimulating, or that I felt the distance between our lives was too great, or that I found them insufficiently curious about me. I also fear that perhaps my past achievements have placed me in a life phase that few people in my age group have already reached, causing a mismatch between my age expectations and life phase expectations. It is also possible that I fail to feel physically attraction and rationalize the lack of attraction by emphasizing another possible cause of mismatch. Perhaps, too, it is a defense mechanism in reaction to a subconscious fear. Finally, I am also theorizing that perhaps the way I have chosen to advertise myself caused matches with the wrong type of people at the start of the funnel.

These are just theories though, and I have not yet figured how to test them. It is also possible that the outcome of each encounter could be explained by a combination of these factors.

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I am also starting to talk to friends more openly about this predicament. (Not necessarily to ask for advice—sometimes venting is already enough!) As part of one of these conversations, a person I respect and admire shared with me (paraphrasing):

To me, the first impression you give is someone who is fairly intelligent, analytical and direct. It can easily be perceived as dominant or at least intimidating. However, now that I have learned to know you better, I have also seen you present your more vulnerable side. A soft side that is more focused on feelings, on good connections, attentive to others, who is more self-aware. I wonder how much of this you show when you meet someone new.

Although this conversation happened more than a few weeks ago, I still keep thinking about it. I can indeed admit that my more vulnerable facet (let’s call them “facets”) is not usually visible to newly made acquaintance: as the saying goes, I need to “warm up” to new people. A more accurate description would be that living this facet costs me extra energy, and when something “bad” happens to it (including minor hurt to feelings), it also costs me extra energy to recover. Out of (perceived?) necessity, I have learned to be rather stingy with the occasions where I let this facet show. There is perhaps a lesson to learn here.

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Then, later, another topic came up. I have been rather frequently asked “how I use my free time”. Initially casual and non-committal about it, I started to feel the importance of this question more, and thus began to take it seriously. After much reflection on this particular topic, I cannot do anything but conclude: I am truly a boring person. Hah.

My usual hobbies in my free time are that of an old man! I like to work in and on my yard, water my plants, tinker with my home automation, do my review homework for my city council. I love long walks outside. My favorite activity is spending time with my friends, which I do by sitting together, eating together, or going on walks together, to just talk. Even my travels are primarily organized to meet friends (and sit/eat/walk together, to just talk).

Meanwhile, on the topic of main occupations and ambitions, I am already rather content. The hard things I had wanted to achieve in the past were achieved, and I feel a clear path for the hard things I want to achieve in the future. I practice physical exercise and care for my diet and addictive tendencies and expect life partners to do so as well, but these are neither occupation or hobbies; they classify alongside brushing one’s teeth every day. Overall, there is less struggle and angst in my life than there had been before.

On the surface, this is objectively the appearance of a boring life. Maybe I am boring, and mirror boring when I meet folk? Perhaps I should not be surprised to find boring if I present boring.

Yet… this is not the entire truth either!

There is snowboarding. This one, I readily advertise. In the same category, there are other things like mountainbiking, playing trampoline dodgeball, ballroom dancing, as well as more sensual physical occupations in more or less social settings. These are the activities where my brain can switch off entirely; where I can experience pure pleasure and joy and feel the maximum amount of connection with other participants, albeit for a short period.

These activities I do not advertise because I do not practice them regularly. But perhaps I should? Even though I do not practice them regularly, I do seek this category frequently. They do form a large part of my perceived experience of life, even if they are not a large part of my free time. This feels quite important?

This is truly another “facet” like the other two already identified above. A more “intense, flow-based experiential” facet. Compared to the analytical facet and the empathetic facet identified above which I show very consciously and therefore can talk about readily, this third facet erases my sense of self and thus escapes my language abilities during conversations.

How to integrate these insights in my dating program?

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By developing the above in conversations, I received the following feedback:

• on the “I am boring” topic. Gardening, walks and talking with friends are in fact the features of an examined good life, per Voltaire and Epicurus. Perhaps it reads as dull, but it could also be advertised as a continuous achievement.
• regarding the flow facet that escapes language. It is connected to Wittgenstein’s philosophical point “whereof one cannot speak, thereof one must be silent.” That should reframe the difficulty: it may not be a personal limitation that this facet escapes my language abilities; it might be structurally pre-verbal, which means the dating-conversation format is the wrong instrument for it. I may not need to talk about snowboarding; I may need a date who is there on the mountain!
• regarding the meta-pattern. I am deploying my analytical facet (theories, funnels, A/B-testing self-presentation, “I have not yet figured how to test them”) on the one domain the third facet tells us yields to the opposite of analysis. It’s like the Taoist wu wei, the archer in Herrigel’s Zen in the Art of Archery who can only hit the target by not aiming, and the centipede’s dilemma (the centipede walks fine until asked how, and then can’t walk at all). Maybe the “click” I’m hunting is, almost by construction, the thing the funnel-mindset cannot manufacture.
• maybe the method I chose (serial first dates) is working against the grain. If I look back in time, I see that I have built friendships through repeated contact in low-stake shared contexts, with lots of warm up. Then I adopted high-volume serial first dates, “like a part-time job”, a method that is the precise structural opposite: one-shot, high-stakes, evaluative, stranger, no repetition, no warm-up, maximal exposure of the one facet (analytical, “intimidating”) that reads worst on first contact and offers minimal room for the two facets that actually make me lovable. Maybe the funnel approach wasn’t the right approach.

That sounds like another insight. But then, what to do?

Yes, I am aware that meeting people on the slopes would probably be fruitful in my case, but living in the Netherlands it is also highly impractical. Are there possibly other high-intensity, flow-based activities I could engage in more regularly and frequently? I can see two possible advantages. One is that engaging more frequently in flow-based activities could teach me to exhibit my emotional facet more comfortably in other contexts. The other possible advantage would be that it would expose me to new social contexts with people who share those interests and whom I could see more regularly and bond with.

I have not found these activities yet. For many candidates (e.g. team sports), my schedule offers too little room alongside my other commitments in the evenings. For some others (e.g. ballroom dancing) I have already established that the kind of people who attend are too far from my values and interests to properly bond with. More search is needed.

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Another angle to consider: high-volume serial dating also depletes my energy and reduces the time I can make available for others (and other activities too). My vulnerable facet costs extra energy to show and extra energy to recover when it’s hurt; serial first dates are a machine for delivering small, repeated hurts to exactly that facet. The method burns the fuel it requires.

Paradoxically, spending time in flow activities and hoping to meet there people to connect with is still like a funnel, and likely impaired by the same limitation.

Maybe the strategy could be to embed myself in a community Id’d want to be in regardless of dating, with repeated low-stakes contact and built-in warm-up, and let connection emerge as a byproduct. Maybe the friendship-first / slow-burn model is my “native” relationship-building mode, and I should find a way to extend it to romance. But then if I do this with a goal to eventually find romantic connection, I fear I’d be entering the funnel mindset again. Therefore, “just participating in communities” does not feel like a clear winner strategy either.