Shyness is, or at least can be an endearing trait. But in terms of flirting, it can feel like the kiss of death.  Even the thought of going up and talking to a woman you’re attracted to can be absolutely paralyzing. But of course, if you don’t do it…if you don’t put yourself out there, then you’ll never find that special someone.

So what to do about it?

You’re in luck.  The brief guide below will help you break out of your shell and flirt with the best of them.

Play To Your Strengths

As mentioned, shyness can be an endearing trait, so use it.  That might seem counter-intuitive at first blush, but here’s the thing:  You’ve obviously got to display some basic level of confidence to attract her, but that can be laced through with shyness.  So when you look over at her and smile shyly, then look away (because every fiber of your being is telling you that you should), be sure to muster up the courage to look back at her again.

shy_guyIf you observe her behaving the same way, she’s sending you an unspoken invitation to come talk to her, and that should help quell the jitters – after all, you’ve just been invited!

Put The Ball In Her Court

One of the best and most powerful tools a shy guy can use to get a conversation started is to ask a question.  The particulars of the question don’t matter as much as the fact that you say something.  So for instance, if you’re at a coffee shop, “I’m not sure what I want today – what are you having?”

That simple question can’t be answered with a yes or no, and whatever her answer is, it opens the door for another question, and before you know it, you’re having an actual conversation!

See, starting is the hardest part.  Once you’re talking, it’s pretty easy to keep finding things to talk about.  One shy guy I know actually began by walking up to a girl and saying, “give me a minute – I’m trying to think of something charming to say!”  She laughed and invited him to sit down, and they’ve been dating for two years.


complimentCompliments can be a great way to start the conversation, but you’ve got to be careful, and you’ve got to make sure that you have something else to say after that.  Otherwise, you could fall into a situation like this:

“That’s a beautiful dress you have on.”



And now you have nothing to say, and walk off, feeling mortified.  A much better approach would be to “practice” the conversation in your own head before you actually have it so that you’ve got a response or reply and can continue the conversation for at least a minute or two without feeling self-conscious about it.

Don’t Overthink

One of the reasons flirting is so tough for shy guys is that they tend to over-analyze.  Stop doing this.  Honestly, what is the worst that will happen?  It’s not like she’s going to start screaming for the police at the top of her lungs. So push your comfort zone a little.  It’s thirty to sixty seconds of your life.  If she’s not receptive, you didn’t get hurt, you don’t have any broken bones, then give yourself a pat on the back that you tried, right?

Flirting is fun, even for shy guys.  You’ve just got to train your brain to at least temporarily allow your personality to shine past the shyness.  If you can do that, the women who are interested in will admire you for both your courage to step out of your comfort zone and for your shyness.  That’s win-win.