Don’t Chase the “Yes”

“Hey – you’re really cute and I had to come up and say hi”.

One of the most transformational periods of my life happened back in 2013 when as a high school senior, I went up to UC Berkeley twice a week to cold approach and pick up girls. The catalyst for this pursuit was heartbreak, and what stemmed a raw determination to prove to everyone else that even a shy, socially anxious, teenage Jerry had what it took to get with cute girls.

I was a very different person back then. Quiet. Timid. And with so much social anxiety that I couldn’t even get myself to turn to the girl sitting next to me in class to ask to borrow her pen without triple guessing what I needed to say. Pick up spoke to me deeply, as a skill set like playing the violin or solving competitive math problems, that I could optimize against linearly by learning what to say, how to say it, and how to hold myself. Where previously nebulous social interactions became structured in stages – learning openers, establishing premise, keeping up social momentum and escalation. And each time I took the bus up to UC Berkeley, I studied my game, and improved my results. Opening up more girls. Getting more numbers. Converting to more dates. To that timid high school Jerry – he was living a life never thought possible. And finally for the first time in my life, everything felt right.

There’s a number of positive realizations that came from this, including most pivotally that limitations in your life are often set by yourself, and that reality is yours to make of it. But as I got more numbers and gained outward confidence (which is easy when you “know” exactly what to do), the insidious truth was I was also shutting myself off from building genuine connections both romantically and platonically with those around me. When everything in life becomes a game you can optimize to get better at, you start blaming yourself for “not doing better because you know better” and spiral into disillusionment of the end outcome being just a matter of practice. Now, fast forward nearly a decade, I’m finally coming to terms with this cynicism and learning to overcome it.

My philosophy towards dating has drastically changed in the last year. As someone who often wonders “what’s the point,” having learned pickup establishes the value of an interaction to solely be dictated by the end result – whether it’s reaching XYZ “base” with a person of interest or even forming a romantic relationship. But when life distills to a series of “achievements”, each achievement dilutes the next and slowly loses meaning. That by the time you sleep with that girl you have a crush on, you wake up the next day feeling empty. Or even if you successfully chase a girl who decides to be your girlfriend, if that is the sole goal, eventually when the initial sparks fade, you begin to wonder again, “what’s the point”.

I’ve spent most of my adult life disillusioned about dating for that very reason, and as I’ve gotten more “success,” the more difficult it has become to answer that very question. But as I’ve opened up my heart more and learned to live in the present vs figuring out the next step of my playbook, I’ve realized the goal isn’t to sleep with someone, nor is it even to get into a relationship. The goal ends up being the connection you foster and share with someone you care about – the conversations, shared experiences, and having a profound understanding of who they are as it matches with you.

That the connection between you two – which is unique to each romantic or platonic relationship – requires time and effort to grow. And that in the end when you finally want to make that step forward and ask that girl out on a date, what you’re chasing no longer ends up being the “yes,” but rather the shared connection you and her have built up over time. That even if it means not being able to “optimize” the next step of the escalation ladder in as little of time as possible with as many people as possible, that genuine connection you build makes it all worthwhile.

As someone who was trained in partner dancing (ballroom), I’ve started to view every interaction, conversation, experience as a dance between two people. Where each person’s vibe and energy helps complement the other, which all comes together in a beautiful push-pull dynamic that becomes greater than the sum of its parts as both individuals move across time and experience. In a place where love, including platonic love, can foster and grow. The results are never what you originally expect. And that’s the beauty of it all.

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