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?
Approval-Seeking ⇒ Playful Evaluation
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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?