December 11, 2019

How I (Finally) Learned To Flirt

Hello Doll,

I used to suck at flirting. Big time. I was so terrified at the prospect of flirting that I went to great lengths to make sure no one could ever accuse me of being flirtatious.

I didn’t know how to “send signals” or “feel the situation out.” I would either write him a letter proclaiming my love or avoid eye contact like he was Medusa and I was afraid I’d be turned to stone.

At some point, it occurred to me that this was a serious problem. I really wanted love, and I knew intuitively that if nothing else, the state of my flirting skills was not helping matters.

I decided to put myself through my own flirting bootcamp. And it worked! Now I can flirt like a champ. (Next time you see me I’m happy to demo this for you!)

Here are my 4 biggest tips on how you too can master the art of flirting.

#1 Understand what flirting is, and what it isn’t

Back then, I primarily saw flirting as an opportunity to be rejected.

Now, I define flirting as actions intended to make someone feel seen, special, and acknowledged. How important is that?? Whether it’s a stranger or your husband, there’s no downside to having flirting skills.

As far as I’m concerned, flirting is a tool you can use to see if you’re interested in someone, because their reaction to your flirting will help you know if there’s something between you worth paying attention to. And it’s a tool to deepen your connection once you’re romantically involved.

Flirting can (and should be) fun! It might only last for 30 seconds and not go any further and that’s OK!

Flirting is not:

  • a promise of sex

  • an act of desperation

  • a sign that you know you’re interested

#2 Let go of your unhelpful “flirting story”

For me that story was that some people were good at flirting and others (like me) just weren’t. There was also a subplot of not being attractive enough. It wasn’t a helpful story and it didn’t have a happy ending.

Some people are naturally good at swimming, and some people work hard to learn how to swim. When it’s all said and done, the person who’s a natural isn’t necessarily the best. Why? Because skills can be learned, taught, strengthened, and even weakened through neglect.

I chose to consider the possibility that my inability to flirt meant nothing more than I hadn’t yet developed the skill of flirting.

What’s your flirting story? Are you willing to consider that it’s not true, or doesn’t have to be?

#3 Observe flirtatious humans in the wild

I honestly did this. I would go out into the “field” (hanging out with my friends) and pay attention to which of my friends were easily meeting guys and which ones weren’t, and why.

The answer was never that one person was more attractive, or even more outgoing. It was always that the good flirters had nonverbal ways to signal their interest or approachability.

#4 Practice, practice, practice

There are different styles of flirting and levels of aggressiveness. But the single biggest thing I learned from my field work was that I wasn’t going to get anywhere without getting comfortable making eye contact with strangers. And so I started practicing – with all sorts of people in all sorts of settings.

The supermarket cashier, the mailman, the random person on the elevator – everyone was fair game! Watching how uncomfortable many people are with eye contact was even helpful. I knew they “shouldn’t” be nervous to smile at me, and it helped me realize I shouldn’t be nervous to smile at anyone else.

Once I mastered eye contact, all of these things started happening that I couldn’t have previously imagined. I met men in all sorts of settings, I started having fun dating and connecting with guys, and my overall romantic confidence soared.

Do you want to get better at flirting? If so, there’s no time like the present.


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