Conquering Your Shyness – 9 Dating Tips for Introverted Guys

Conquering Your Shyness – 9 Dating Tips for Introverted Guys

By | 2018-04-21T12:11:47+00:00 January 26th, 2018|Categories: Blog|2 Comments

Reaching out to someone new is scary! More for some than others. For me, it’s a case of sweaty palms, increased heart rate and fumbling over my words.

If you’re an introvert, you can relate.

Introverts have a hard time dating because socializing doesn’t come naturally to us. We feel safe behind our phone screens. It’s the face-to-face interaction that’s difficult.

Online dating has definitely taken a backseat in my life. There are many reasons why I am not doing it right now, and one of them is because I don’t want to hide anymore.

I really want to step out of my comfort zone and meet someone organically. I’m tired of sharing my attention with more than one person. And I’m tired of having to share someone I like with other potential “candidates”.

It’s nothing personal. Online dating just isn’t for me. Simple as that. A friend of mine put it so perfectly into perspective. This is what they said:

“…online dating is the problem with us both… The girls on these sites have a sense of desperation from loneliness or a broken heart which you cannot fix by moving on, you need to be whole first. The guys also have a sense of hormonal desperation and seeing photos first, choosing sexy over a real person who might not be as perfect in looks is ultimately what happens. So…desperation is not how you start anything… And knowing immediately that you are both single and “ready” makes temptation so much easier… And friendship is shortened, relationships are rushed and you can’t love someone you don’t actually know. I know there are a few successes on these sites, but ask them all… FRIENDS FIRST!”

These are the pitfalls of online dating, and to be honest with you—I think I am totally DONE meeting people like that.

But this puts me in a precarious position—one where I’m uncertain of how to meet someone. How do I get a woman’s attention? How do I talk to her? How do I know if she’s interested? How do I even know she’s single?

It is difficult, but not impossible. Today I want us to forget about online dating—COMPLETELY. This is all about meeting someone the old-fashioned way.

Are you in?


Remember: You Have Nothing to Lose

You’re single.

You meet someone you like and the first thing your mind does is tell you what NOT to do.

“Don’t stare too long.”

“Don’t say something stupid.”

“Don’t embarrass yourself.”

But as you know, I’m a YES MAN. I say “Yes” to everything. So let’s start focusing on what you SHOULD do rather than what you shouldn’t.

You see I firmly believe that we regret more the things we don’t do, than the things we do. So let me reiterate something: YOU ARE SINGLE!

You have nothing to lose speaking to a girl you’ve just met. If she rejects you or acts weird, you’ll probably never see her again anyway. She’ll probably be awkwardly flattered and let you down politely.

You took a gamble and it didn’t pay off. So what? Life goes on.

Oh and one more thing… She may NOT reject you. She may actually respond positively. Ever think about that?


Be Genuinely Interested

As most of you know… #iHateSmallTalk

An intelligent woman can tell whether you are genuinely interested in her. If you’re letting your hormones guide your actions & words, you’re probably going to look like an ignorant oaf who can’t rub two sentences together.

But if you really like her, show some genuine interest. Listen intently. Watch her body language. Ask questions out of real interest—not just to make empty conversation.


Play to Your Strengths

What are you really good at? Think about that one thing that puts fire in your eyes.

I love this saying: “Soulmates find each other eventually because they have the same hiding place.”

What’s your hiding place, and who else is there waiting for you to notice them?

I’d like to think that the perfect match for me is someone who likes at least one thing as much as I do. And if you can bring this common denominator into a conversation, the rest will be easy. That common ground will pave the way for easy conversations, synchronized humor and tons of topics to delve into.

So if she says she likes reading, don’t say you do too for the sake of forcing common ground. Find REAL common ground and take it from there.


Stop Thinking People Don’t Want to Talk to You

I honestly used to think people had no interest in talking to me. I think all introverts go through that. We feel almost as if our conversation is an imposition to people because we are socially awkward.

We are not interested in speaking to someone who isn’t giving us their full attention. We don’t like raising our voices so that we can be heard.

So we keep quiet.

But there really are people out there (extroverted people) who want to hear what you have to say. They are willing to listen.

So don’t let that silly fear stop you from approaching someone new you like. Maybe she wants to talk with you as much as you want to talk with her. You won’t know unless you try.


Do Something Different to Grab Her Attention

There’s no perfect recipe for getting a woman’s full attention and peaking her interest. You’ve got to be creative. Maybe even slightly romantic.

Again, playing to your strengths as discussed above is one way you can try. But be original. Any guy can talk to this girl, buy her a drink or use a silly pickup line—especially if he’s a guy who’s perceived as better looking than you.

So be different. Do something unique. Make sure she remembers you. You don’t have a phone screen to hide behind, so show some confidence and take a bold leap.

Your gesture may be better received than your fearful mind is telling you.


Write Your Own Love Story

I want you to be honest with yourself.

Why do you like this girl? No, really? What is it about her that’s different to the blonde sitting three seats away? Why is she more special?

If your answer has anything to do with her looks, you’re on the wrong track. Looks are a dime a dozen my friend. Yes, I think attraction is extremely important! And don’t even get me started on sex! But it’s her personality that should win your heart.

What unique characteristic caught your attention? What’s that something she has that you won’t find in anyone else? Answer this question honestly.

And when you finally get up the nerve to talk to her, tell her that you noticed that uniqueness.


Stop Overthinking Your Approach

I have a confession to make: I am really bad at following my own advice. And this is where I struggle the most.

I over analyze every little text message, every word I say to someone, their facial reactions in conversation, their tone of voice, how I responded to a question… it drives me INSANE.

We need to stop overthinking everything. Why? Because being yourself is the most attractive thing you can do.

So just be yourself. If people don’t appreciate you for who you are, they will eventually fade away from your life. Allow that to happen. As the Dalai Lama is well known for saying, “Remember, sometimes not getting what you want is a wonderful stroke of luck.”

NEWSFLASH: Intelligent, grounded woman already think like this. It’s time we did too.


Be Yourself. Be Her Friend.

I know it’s so cliché to say this, but it really is the best advice for introverts.

I’m always telling you not to wear a mask, and I’m saying it again now. DON’T WEAR A MASK!

Pretending to be someone you’re not is going to bite you in the ass later on.

I believe in being completely honest with people. Telling someone how you feel about them is an important characteristic to develop if you want to deepen your relationships.

But first contact with someone new is not that simple. You can’t go up to a girl and tell her you really like her and think the two of you could have a great future together. That’s just creepy!

(Don’t be creepy)

Instead, see it as a friendship. Yes, there will be flirting. Yes, you both know there’s a spark. But friendship first. It’s a non-negotiable.


Don’t Be Afraid of Rejection

When you step out of your comfort zone, you must prepare yourself for rejection. As a business owner I have survived countless failures, bad months, and heart-breaking extractions from my savings.

But I’m not afraid to fail. If I was, I wouldn’t get very far in life.

I’m not afraid of rejection either.

If you can eliminate the fear of rejection from your approach, you’ll have the guts to speak to women more freely—and without that looming fear of being shut down.

Hey, if she shuts down the conversation, you can at least say you tried. Shrug it off and put it down to “not meant to be”.


I hope this has helped you to find the courage to talk to that girl at work; or the one living next door; or the one you met somewhere ‘so random’ 😉


Good luck guys

Stay safe


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  1. Symona August 5, 2018 at 6:41 am - Reply

    Me and this article, sitting in a tree, L-GER-A-N-I-N–!

  2. Copley Sutton June 20, 2019 at 12:10 pm - Reply

    😀 Thanks Symona!

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