Approval-Seeking -> Playful Evaluation

Enjoying the In-Between

For a long time, I related to flirting as a challenge. At stake was my social worth — with the woman holding the power of social approval.¹ My role was to perform my part, impress and showcase my best sides.

Holding this view meant relinquishing my power.

This way of relating has an undercurrent of scarcity — focusing on not “wasting an opportunity”. My goal-orientation crowded out my preferences, making me forget to feel into what I wanted.

When I don’t have social anxiety, I don’t go into approval-seeking. When I tried temporarily disabling my social anxiety, I naturally settled in on another framing — that of playful evaluation. In this frame, I use flirting to playfully evaluate potential partners.

At an event, I was cuddling with a woman I was attracted to, and we were talking about our sexual preferences. We weren’t a great match, and she had a monogamish boyfriend. I told her that I wasn’t interested in intimacy, but still wanted to flirt.

After a moment to process — “ignoring 15 years of programming” — she happily agreed.

I intentionally went into an insecure-attachment-esque way of relating — treating her as an unreachable object of desire. I enjoyed the sensation of “wanting her” while knowing, at some level, that I didn’t actually want her.

Historically, I’ve hated being in needy approval-seeking states. Going at it in a playful way allowed me to relax a bit, feeling needy without taking it seriously. Knowing that I didn’t actually want things to go anywhere allowed me to relax, feeling a sense of expansion instead of contracting due to shame.

In this expanded state, I enjoyed flirting — giving her oblique compliments and innuendos, while leaning into mixed feelings of shyness and audacity. A great time was had by all.²

Disconnecting flirting from approval-seeking has given me a lot of freedom. I’ve developed one semi-permanent flirting friend — a heavily communicated friendship that is permanently on the verge of becoming something more, with mutual attraction but no real interest in intimacy.

I used to hate being in this in-between state, finding it neediness-inducing and anxiety-provoking. With my new mindset, I’m able to play with flirting dynamics, even staying in the state in-between.

Letting go of the performance anxiety has opened up my ability to talk and find mutually agreeable agreements. Approval-seeking used to block me from talking frankly — playfulness has set me free.

Where in your life do you seek approval? When do you try to impress, performing rather than finding ways to connect? Dating, employment, friendships?

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P.S: I’d love to guide you through an inquiry on the things that matter to you. Sessions are 60-90 min, and run in the gifting economy (pay what you want).

Here’s a statement from my client Frans-Lukas, shared with his consent:

“I've attended Jonathan's philosophical guidance sessions four times, and the experience has been transformative. […] I often share the concepts discovered in Jonathan's sessions with my friends, and they've significantly impacted my life.“

1. Calling up her friends, a jury of peers.

2. I checked in with her at the end of the event, synchronizing realities and making sure we didn’t let lingering effects of the role-playing “bleed” over into real-life.