Published on July 11, 2025 9:31 PM GMT
A mindset that resolved a lot of my personal anxiety for dating: I'm not trying to convince anyone to like me… I'm filtering for people who are already a good match.[1]
When this mindset is accessible, the concepts of “flirting well”, “fumbling”, and “success” start to feel funny and even meaningless.
When my girlfriend and I got together, I felt extremely attracted to her but I wasn’t anxious about whether or not she liked me back. I had no pull to “convince” her to be with me. Instead, it felt like: “Are we in the timeline where we work out? Let’s see!” It felt really, really relaxed.
Put another way:
I’d prefer to flirt with and attract people who are charmed by my most relaxed self, and less with everyone else.
“But what if my relaxed self isn’t a good fit with anyone???”
SO this is what I ultimately needed to feel secure with: the possibility of ending up alone. Once I felt secure with that, dating became much easier!
To be clear, I wasn’t always like this!
What changed was that I found a way to feel secure with all possibilities of not dating her (or anyone), ending up alone, etc. This involved working with a decent facilitator, learning to trust my intuitions/feelings, and ultimately developing my own theories of unlearning.
Ironically, when you feel secure with outcomes, you become more attractive. People who feel secure with the possibility of not dating are less needy! Dating is a Newcomb Problem:
- ^
I don’t actually know if long-term romantic compatibility is fixed — this is basically a debate about free will — but it’s useful!
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