Healthy Flirting vs Unhealthy Flirting – The Art of the Enjoyable Attraction

By Dr. Keith Witt
June 25, 2013

Flirting often naturally happens when a more masculine person (usually a guy) and a more feminine person (usually a woman) connect.

This is not to say that any of us is purely masculine or feminine. All of us have masculine and feminine qualities. Ask any gender researcher, and they’ll tell you there are more differences and variations within all women and all men than between men and women. This reflects the incredible diversity and complexity of humans.


That being said, almost everyone is more masculine or more feminine in their deepest essence when it comes to the sexual occasion. You are either more lit up being the leader in the dance, being nourished by feminine erotic light, or the follower in the dance, allowing yourself to be guided to deeper pleasure by masculine depth and presence. When people connect in any way, they create little sparks between each other—polarities—that can be sexual polarities when a more masculine person connects with a more feminine person. These aren’t always consciously felt as sexual. “He seemed so nice,” or, “I loved her smile,” reflect pleasure in this person’s aura—pleasure that often has some subtle-to-obvious sexual component that we might or might not be aware of.

So what about flirting?

When attraction happens, signals are exchanged, and sometimes relationships begin to form instantaneously. I walk through the park on my way home from swimming and pass an attractive woman walking towards the pool, towel and fins in hand. I smile and wish her a good swim. She smiles back. I’m aware of her friendliness and feminine radiance, and she is relaxed and positive with my Keith presence. Seems like healthy flirting to me.

But what if I pressed my flirting?

Tried to converse more, asked for her name or contact information? Extended the conversation because she is magnetic and I don’t want to let go of the erotic charge? She finds this either icky and feels unsafe and repelled, or is flattered and interested and so participates, giving me more access and encouragement. Either way I’ve pressed the flirting boundary too far. I’ve taken a normal attraction, fed it, and I’m on the way to a distracting attraction (no longer an enjoyable casual exchange, but now more personal and obsessive) where I’m likely to keep thinking about her or even pursue her (see blogs #31, #47, #50, and #69). If a couple of single people negotiate a flirtation into deeper engagement, that can be very cool—if you’re single, feeding flirtations is a valuable skill in having fun and finding lovers. This requires being attuned to yourself and the other person (being aware of what you’re feeling and doing with positive intent) and generating the right energy for the moment—skills that can be learned and refined. Since I’m a married guy who knows how amplifying erotic polarity (in this case, pushing a flirtation) potentially leads to nightmare dramas for partnered people, extending the park encounter seems like unhealthy flirting to me. Healthy flirting — spreads good vibes, helps us feel generous and attractive, is welcomed by others, and under the right circumstances can lead to juicy relationships. Unhealthy flirting — risks soap opera dramas, turns people off, or takes them dangerously close to distracting attractions, romantic infatuations, and secret affairs. Since erotic polarities naturally constellate when masculine and feminine people are around each other, it behooves us to have solid guidelines. We flirt all the time—whether we’re conscious of it or not—so let’s flirt well. Let’s feel the polarities and feed them just enough to have fun and help others feel known, seen, and attractive, but never so much that bad stuff happens. Try to observe flirtation in all its forms this week. When you flirt, keep reaching for everyone-feels-great sweet spots in the polarities. You’ll find you can adjust the intensity and quality of the energies to suit both your instincts and your values, and you’ll notice others enjoying and trusting you when you get it right. The more conscious you are, the more choices you have, and principles can guide and focus our choices.

Let’s flirt a lot, but always keep it clean and beautiful.

Click HERE to view the episode of Therapist in the Wild that deals with Healthy Flirting and the art of the Enjoyable Attraction.

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