9 Steps to Empowered Flirting

What is Empowered Flirting? It’s being empowered to initiate conversation and make our attraction known, to find out if it’s reciprocated. Why sit around waiting for others to decide who you meet when you can decide for yourself who you get to meet?

“If you throw yourself at everything, you’re bound to stick to something.” – Digger’s mantra

For most of us, the fear of rejection limits our flirting and who we meet. Probably because we’ve watched way too much Hollywood schtick that loves to turn such scenes into humiliating hilarity. As an aging slut, I’ve found that the world doesn’t work that way.

In the decades I have been at this, I have never suffered even remotely such ridiculousness. In the many hundreds of men I have approached and flirted with, only maybe 2 or 3 were impolite which only went as far as a cold shoulder – no response. The rest were polite either in their interest or in their disinterest, and it was often very clear. But I also got flirt technique.

If you are interested in empowered flirting, here are 9 steps that worked for me. It’s a practice, but once developed, you’ll be surprised how well it works

Step 1: Get over yourself.

It’s not all about you. In fact, it’s probably not about you at all. That may sound rude, but it’s actually quite liberating and empowering.

It’s about him. It’s about what he’s into, about his tastes, about his mood, his availability. Learning to never take anything personally is one of the biggest and most empowering gifts of my recent life and I wish I had learned this earlier.

When I learned to truly not take things personally is when I was really free of the fear of rejection. And this has enabled me to approach and flirt with anyone. Of course not everyone will reciprocate, but if you throw yourself at everything, you’re bound to stick to something.

Several ideas to help you stop taking things personally. First, I highly recommend the book The Four Agreements by Don Miguel Ruiz. This succinct read will help you with the practice, power, and embodiment of this life-changing principle.

Second: check your assumptions. Our interpretations are mostly shaped by our insecurities. When I was younger if someone wasn’t into me, I  assumed it was because I was too skinny because that was my insecurity. Reflecting with good friends can help us see our assumptions. I learned to reinterpret with a story more palatable to my ego: e.g. he’s got a boyfriend. If you don’t know the explanation why not pick the most comfortable option?

Third, I’ve all been hit on by men not my type. I wouldn’t want them to get all sad and personal about it. I’d just like them to move on and find someone right for them. Why should I get all personal about it?

Forth, PRACTICE. That’s right: I practiced getting rejected just to get used to it and then the easier it became. Most of us homosexuals have been humiliated at some point in our lives so most of us avoid humiliating others. Unless that’s what you’re into.

Step 2: Don’t Think. Just Do.

If I see someone I want to approach and I spend anytime thinking, planning, assessing, then the insecurities and nervousness take over. It’s best to just jump in with an unplanned introduction. First I’ll close the distance, move to a place within earshot, without looking like a desperate vulture lurking about. I wait for an opportunity to flirt to arise naturally, rather than pre-plotting it. Eye contact and smiles can work from afar if he is occupied in a conversation, but me personally, that is not my best skill. Conversation is where my personality and peacock feathers really shine so that’s where I try to get to. I don’t want to awkwardly interrupt a conversation he’s having, but in certain social environments it can be normal to join a conversation, throwing in a comment on the topic. I just like to look for the cues if it is welcome or not.

The best opener is just a friendly line, like Hello. I approach him like I might approach a friendly stranger at my best friend’s cocktail party. The first topic is anything we might have in common. e.g. hey how’s your night? Those pastries are good right? Keep it simple. Then I try to move past the small talk straight to a (not-too) personal, inquisitive question like ‘where are you from?’ This shows real interest.

At this time, I just want to see: is this person even interested in chatting with me? Are they interesting enough that I want to continue chatting with them? The best conversationalists ask prompting questions and listen attentively. People love to be heard. Keep an eye out for other people who are good at this and observe them and model. What have you been up to tonight? Where do you live?

I’m looking out for signs of interest such as eye contact, smiling, moving closer, introducing me to friends. There is a certain slow rising smile with eye contact that, is usually a ringer of interest.

If they are uninterested, they may respond with short curt answers that don’t continue the conversation, or look elsewhere, or step away. I’m not going to flirt with someone not interested in chatting with me. If the conversation doesn’t flow I’m not going to pull teeth – although I may try again later as it may have simply been a bad moment. For him or for me.

Step 3: Give Him An Easy Out

I like to give him easy outs, throughout the whole exchange. I don’t need to corner prey here, I want to chat up dudes who reciprocate attraction. Even if they are not attracted to me, I want to make a friendly acquaintance. If I give him an easy out and he doesn’t take it, then he’s probably interested. What are some easy outs? You have to keep an eye out for them, they happen randomly. Just stepping back a bit to see if he continues the conversation is one idea.

Step 4: Give Myself An Easy Out

After some chatting you may find him to be Pretty From Far, But Far From Pretty (aka PFFBFFP, which is also onomatopoeia for a deflating balloon). Give yourself an easy way to exit the conversation if you decide. Something clear and direct is best. A smile and respectful “Nice chatting with you, have a good night” or just “Have a good night” is pretty clear, without making it awkward.

Step 5: Flirt with body language

If it’s going well enough, I like to flirt with my body language and see if it’s reciprocated. I move in a little bit closer than is platonic. I sink my gaze into their eyes, and hold eye contact for 6 or so seconds. I smile, especially that slow to rise smile while maintaining eye contact. It’s usually pretty clear from their body language if they reciprocate or not. In the very rare time it’s not clear, then we probably don’t speak the same body language. Since I’m not interested in dudes I don’t understand then I move on.

Step 6: Go For The Kill

It turns out that most of us are pretty bad at interpreting flirting or not, so if the body language seems to be working, I like to make my attraction crystal clear, often with passing compliment, that feels natural. For example, if he makes me laugh and my brain goes “How cute” then I just let it out ‘How cute’ but the key, for me, is to not leave it hanging so it he feels awkward like he’s supposed to say something. I immediately follow up in the same breath with something else so he hears the compliment but doesn’t feel forced to reply to it. So I might say “How cute, and then what happened?” I’ve seen others go for the kill by asking “So where’s your boyfriend?” Which indicates interest and allows them to clarify if they are available (although around here many guys with boyfriends are available haha so don’t assume!).

Step 7: Jump into the date

I have always thought this is great advice, and will implement when I’m actually looking to date. If it’s all going well and there is clearly interest, immediately start the date. Ask the personal questions you want to know on a date. Where you from? What do you do for fun? What do you do for work?

Step 8: Wrapping it Up

When time runs out, offer to make plans, preferably specific: Hey would you like to get coffee this week? Maybe Tuesday night? Try to put something on the calendar but remember: give him an easy out, don’t be pushy. Another option is more vague – Hey I would love to hangout soon, can I give you my number? I like to give out my number rather than ask I guess it feels less of an imposition.

Step 9: Next Steps

No matter what happens, next time you see them: be friendly. Why not? They may change their mind, you may change yours (it happens). My persistent friendliness and sense of humor has changed minds.  Some guys expressed no interest in me for many times of bumping into them and then all of a sudden, BAM, they see it and are into it. And even if they never are, the more I expand my social circle the more people I get to meet. No need to be sheepish and weird about it, remember: don’t take it personally.


Ok, now it’s time to practice. If you are unsure of your approach ask for feedback from your friends, but only if you are ready to hear something you don’t like and won’t hold it against them. It’s best to ask friends who are actually good it. When I was younger, starting out and felt unsure of myself, I thought of the confident jerks from high school. If there is one thing our current president is good for it’s to remind you that you don’t need to be smart, handsome, nor charming to have a ridiculous amount of confidence. If that P.O.S.P.O.T.U.S. can have confidence like that, ANYONE deserves to have confidence.

I knew I’m much better than those people. I deserve confidence more than they do. So I decided to fake it till I make it. With practice I eventually did make it. Can I walk up to Adonis any day of the week? Probably not, I have my moods. But on many days and in many environments I can. It’s a skill, it takes practice to develop but it’s worth it, and so can you.

BTW, I offer one-on-one coaching for flirting and other social skills, that can include going out into the wild to practice. Be in touch to find out more.

Before you go, I recommend this great video for more great tips…

Leave a Reply

Your email address will not be published.

I accept that my given data and my IP address is sent to a server in the USA only for the purpose of spam prevention through the Akismet program.More information on Akismet and GDPR.

This site uses Akismet to reduce spam. Learn how your comment data is processed.