Dear Enchantress….

Dear Enchantress, 

I am awkward and dorky, I’ve always been, and now I’m completely frustrated. I am ok looking, and have a good job, but when I try to flirt, I’m a mess. I end up mumbling or avoiding the exact person that I’m attracted to or smiling from far away. How am I ever going to get in a relationship? How will I ever get married, and have a family? I worry about this, so I go to social dances and creative classes, and I practice the guitar, sometimes at open mic and once in a while I’ll sing a song I wrote. How can I be a better flirt? I’ll take any help in meeting someone who thinks I’m attracted to them!


Dear Flirt Failure,

I am finding you adorable in writing this, and I also feel your longing to be understood and recognized. I have a great way for you to “flirt.” I’ll share that in a moment, but I want to define flirting in a way that may be helpful. Flirting is you enjoying yourself and sharing that with another. It’s NOT doing something to get someone to know you are attracted to them. You can flirt with animals, babies, random people, even yourself. Flirting is having fun, being present and having NO agenda. The use of flirting to get something is an unhealthy manipulation.

SO, with that being said, I give you this fun homework. Go flirt with folks you are NOT interested in attracting, as practice. Flirt with the postal worker, flirt with the bodega guy, smile and enjoy moments in connection with another being. Stop pressuring yourself, it’s OK to realize who you are attracted to, but once you set your focus and “try” to do something, you’ll most likely fail.

Here is the secret line I love and have seen someone use; and it worked, get ready, here you are: you tell the person “I’m trying to flirt with you.” BRILLIANT!!! I know you might balk at it at first, but it’s the truth, and the truth is sexy and fire. Happy Flirting!

If you have a question for The Enchantress or want to work with her, email her at

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