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Teasing, Play, and Flirtation

Article870 Words • Philosophy, Dating • 10/08/2025

What is flirting?

In my previous work, Towards a Definition of Flirting, I examined various components of flirting to try to see if I could better understand the nature and purposes of flirting. I didn’t get as far as proposing a definition because at that time I didn’t really have any strong enough convictions to want to put one forward.

Only more recently, have I become interested in the concept of “play”, and I quickly found myself zeroing in on the idea of playfulness in flirtation. This in turn led me to develop a more fully fleshed out conceptually engineered definition of flirting.

Flirtation has one main goal that is supported by two sub-goals:

Wooing someone by creating connection and demonstrating interest.

Wooing just means making someone like you.

  • There are plenty of reasons why you would want someone to like you, but the most common reason is to be able to ask the person on a date later.

Flirtatious behavior is a broad category of different actions like flattery, light physical touch, asking astute questions, etc. Anything that builds connection and/or demonstrates interest!

  • I think that building connection helps create attraction. I cannot clearly say the link between connection and attraction but I think they are heavily related. They are even semantically similar (even though this kind of linguistic equivocation is intellectually cheap).
    • Attraction of course makes the other person more likely to respond well to your demonstrated interest.

The intention is key.

  • Many people make the claim that you can flirt harmlessly for amusement with no real intentionality to woo someone. I think that trying to combine these two things makes flirting a bit of a conceptual mess.
  • While I think that someone can of course do things that would be perceived as flirting with someone without actually wanting them, I do believe it ceases to be flirting without real intention.
    • I believe at that point you are playing or wooing someone in a more general sense.

Interest need not be romantic.

  • You can flirt to build rapport with someone that you want to be (better) friends with.
    • This is a bit outside of the norm of how we understand flirting today, but I think that it naturally follows from the definition I have developed.
  • I think people who naturally flirt with everybody are people pleasers/want everyone to like them.
    • Just having charisma would lack the intentionality of wooing which would make the person’s actions fail to be flirting.

What is teasing?

Teasing is being playfully oppositional (intentionally antagonistic without being serious).

  • It is a skill because you have to thread the needle of what is appropriate to the person’s individual tastes.
  • Teasing should ideally go both ways otherwise the bid to play likely was not noticed and/or not accepted.
  • There are a number of strategies that one can employ that are mainly decided by context and/or personal preference.
  • Play is telegraphed by various non-threatening signals (e.g. tone, body language).

Disagreeing: This usually plays out like play fighting or recreational argument.

  • I think that if this is your only move then it just makes you seem like an oppositional person and people won’t really want to talk to you that much.

False Emotion: Pretend or exaggeration emotional responses

  • Disappointment, sadness, physical pain, anger, annoyance are all common emotional responses that you can fake or play up

Misunderstand/Misframe Intentions/Words: “Oh so you’re calling me stupid?”

  • This kind of instigation can lead to escalation so it has to be done carefully, and with the proper kind of tone.

Insults/Stereotyping: “You’re a lawyer? I hope you don’t bill me for this conversation.”

  • Playfully means it is not hateful! You can definitely microagress through this.
  • This can be about a personality, physical quality, identity, etc. of a person.
    • Each person has a different tolerance to what can and cannot be joked about.

How are teasing and flirting connected?

I believe that teasing is the most effective kind of flirting. This is because teasing is playful and play is integral to flirtation.

  • There are also hurtful (bullying, negging) and educative (gentle shaming) modes of teasing, but only the playful kind is effective.
    • The other two have inherent power dynamics putting the teaser over the teased, which does not achieve the desired effect of playfulness which I believe requires some amount of equality.
      • Two children playing house where one is telling the other to do everything does not seem fun to me which means that it fails to be “real” play.

Why is play integral to flirting?

  • I believe that play helps create some plausible deniability since it is distanced from overt seriousness.
    • Play and joking around is something that can be done in all social bonds and types of relationships so one can’t immediately attribute intentionality.
    • Plausible deniability helps with rejection (e.g. the other person is taken or is not otherwise interested).
  • Play is fun!
  • Flattery is not always effective.
    • This isn’t to say that you should be negative, but many people hear the same kind of things or do not internalize it so the words become fairly empty.

Other Philosophy Posts

Philosophical Concepts Mentioned in R.F. Kuang's Katabasis

A list of philosophical concepts in R.F. Kuang's Katabasis, augmented by my recommended further readings.

What is play?

An exploration into what play is (and isn't).

One Love

My argument for there not being any different types of love.

Other Dating Posts

Resisting the Automatic +1

A case for not always bringing your (primary) partner to events.

Towards a Definition of Flirting

How can we learn how to flirt if we don't have a definition of what flirting actually is?

Conversational Pre-Work

A collection of conversational devices that can help you get to know someone better.


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