How to Flirt Properly - Are You Doing it Wrong?

Q: I've figured out to a certain degree that when it comes to flirting, I forgot how "natural" I used to be. All I needed to do was heal parts of myself and present my flirtatious responses more calmly and subtly (to suit my personality).

How to Flirt Properly - Are You Doing it Wrong?

Dear Jenny,


I've figured out to a certain degree that when it comes to flirting, I forgot how "natural" I used to be. All I needed to do was heal parts of myself and present my flirtatious responses more calmly and subtly (to suit my personality).

I'm convinced all men and women can be great at flirting and relating to each other on the whole, but so many people forget to enjoy the moment and instead focus on the sexual aspect.

I believe initial flirting should also be considered a subtle vetting of a person. What is your opinion on these ideas?


Born Again Casanova Rediscovering the Art of Flirting


Dear Born Again Casanova,

I agree 100%. Some people are naturally good at flirting while others seem to fall by the wayside–mostly due to lacking sufficient confidence and feeling "inferior" to the person they're flirting with.

It's funny how when people level up and shoot their shot at someone they believe is above their station (usually looks-wise in the case of men and status-wise in the case of women) they regather all the inhibitions they threw out the window in dealing with other people and they become all the more unbearably stifled and tongue-tied.

I suppose I'm a "natural" at this in that I've never been intimidated by anyone to the point of flirting paralysis. Thus I'm going to offer some tips on how you can achieve this quiet and unassuming sort of mindset when you're flirting with people–no matter who they are and how hot, successful, or desirable they appear to be.

I've been around so many different people from all walks of life in my lifetime and the one thing I've learned through these ever-fluid experiences is this:

No one is unsusceptible to charm. NO ONE is immune to charm nor are they above it or beneath it.

So firstly you must remember:

1) The person you are dealing with is a human being. They put their pants on one leg at a time like everybody else.

2) People want to be charmed. And the reason so many people grow tired and frustrated rather quickly with people who engage them is because they're not being charmed. People want to be emotionally and intellectually stimulated by a potential romantic interest, not bored or frustrated to tears.

3) The more charming you are, the more disarming you will be to the other person–and they will quickly open up to you. They simply can't help but to open up to you. They will be drawn to you. They will crave your energy like a bear rooting through a steaming trash pile in the middle of a campground.

Charm is definitely subtle, but it's also very much in your face. People know it when they see it and it becomes like a drug to them. It is so dangerously inviting and intoxicating to people they will line up for you just for a chance to be addicted to it.

So how can you be more charming and rope people in?

As you mentioned–subtlety. For instance when someone texts you, "How you be?"

You text back, "I be good af. No other way to be is there? How bout you? lol"

This hits 3 very high notes:

a) You're imitating their vernacular in establishing a rapport that signals you are "molding" yourself to their liking and their style, and they feel more at ease in talking to you.

b) It's positive energy. You've shown you can have a good time with someone just through one simple quip and some wordplay. And it helps the other person feel relaxed.

c) It's intriguing. "Why does this person seem so fun, carefree and creative all at once?" It's mysterious and they want to know more.

Flirting as an art form is shrouded in mystery, imagination and enthrallment. They become captivated by your mystery in imagining what you're thinking through the subtlety of your words and actions.

As far as using sexual undertones, that's what they should be, undertones. You can definitely drop sexual hints without going all the way and risking becoming too clumsy and awkward too early in the interaction.

People don't want to be forced, they want to be led astray. They want to be lured and enticed into liking you via the cleverest of interactions. As soon as it becomes awkward, a chore, boring, trite or predictable, people shut down and poof, it's over.

In the future I'll be offering more hands-on material on how to charm the pants off people and be a consistent winner at this game. And the people who choose to employ it will win hand over fist in today's sea of people who possess no social skills and insist charm is only something they wipe their rear ends with.

Don't live in your head and make assumptions about what people are thinking. But do allow yourself to be a "natural" in paying attention to what's going on with the people around you and concentrate on having a blast. That should be your focal point.

And with the sexual stuff, less is more. Only time you should be kicking that up a notch is when they're already finding you helplessly irresistible because of your charm.

Good luck and happy flirting.

Love and Many Blessings,


P.S. My followup column on Self-Esteem Building for Men will be published tomorrow evening so make sure you stay tuned for it.