Extrovert Girls, Here's How to Interact With Shy Guys
Extrovert Girls, Here's How to Interact With Shy Guys

6 Tips for Flirting with Shy Guys

Shy guys aren’t from a different planet, so get over your reservations and just talk to them.
April 13, 2016
6 mins read

Finding a decent man nowadays is like to trying to find a needle in a haystack.

So, in other words, practically impossible. I’ve always found myself assuming that being an extrovert will help in the process of finding a guy, but you know what they say about “assuming.”

Because what if it’s not easier? What if the person you’re trying to interact with is shy? What’s a girl to do? People always say opposites attract, and there is quite possibly some truth to the statement.

But what do you do if your “opposites” make meeting and potentially having a chance at something impossible?

Being an extrovert, I’ll be the first one to raise my hand and admit the truth. I never know what to do when I’m interested in a guy who is shy!

Do they seem sweet? Absolutely. But how do I relate to them? I’m a loud, “never met a stranger” type of girl, so I never know if my “normal” is going to seem normal to them or freak them out and send them running for the hills.

Having said this, I’ve consulted some friends and I’ve decided to make a list of the best ways for an extrovert, like myself, to interact with someone who is shy.

1. You Need to Initiate

What I find to be one of the most important things is finding a reason to talk to them. If the guy you’ve set your sights on really is shy, he likely won’t initiate a conversation with you.

But, I’ve noticed walking over to talk to a shy guy when you have no reason tends to make him uncomfortable. You might find an extra challenge in coming up with a reason to start talking to him, but, who knows, you might actually have a meaningful conversation rather than just random flirting.

So, you might consider taking a few minutes to brainstorm some ideas before you walk over to him.

2. Don’t Try Flirting 

If I’m going to strike up a conversation with a random guy I’m interested in, the “go to” way to start is by flirting a little.

But shy guys are different. They may not feel comfortable with your forward approach.

So, if you want your first interaction with him to turn into a second one, try just being friendly the first time you talk to him. Let the flirting come naturally in the course of your (hopefully) future interactions.

You don’t want to scare him away by coming on too strong.

3. Give Him an Opportunity to Talk

I know I’m not the only one who has caught themselves in a conversation talking a mile a minute.

Because I can be prone to talk with no end in sight, I find I have to consciously stop myself and actually give the poor guy an opportunity to talk back. After all, they call it a conversation for a reason, and the idea is for both of you to talk! You never want your interactions to be a one-way conversation.

He also isn’t likely to interrupt, which could mean you would be rambling through the whole conversation.

I had two best friends in high school who were shy, and I had the realization fairly late into our friendship how one-sided our conversations were. Most of the times we hung out consisted of me talking and them listening, nodding or agreeing.

Let’s all take a minute and be thankful I wasn’t interested in either of them.

4. Don’t Ask a Lot of Questions

I love asking questions! They’re pretty much the best and easiest way to break the ice with someone new. But if you’re trying to interact with a guy who is shy, the chances are he doesn’t want to answer an abundance of personal questions about himself and his life.

And there goes the easiest way to start a conversation.

You want to try and work the conversation in the right way, to keep him from feeling like he has to talk about himself too much.

Now, I’m not giving anyone permission for any extra narcissism. Don’t make the entire interaction just about yourself. Talk about a major loss of points in his book! Just try to keep questions out of the conversation. If you do need to ask any, be sure to keep them open-ended. Always try to avoid yes and no questions.

5. Befriend Him

In my opinion, all relationships should begin as friendships, but this relates specifically to you and the shy guy you have your eye on. A relationship will hopefully come soon, but he’s going to feel much more comfortable with the idea of becoming your friend first.

I never said the process was quick. What a great opportunity to work on your patience.

Trust me, shy guys are not bad and they’re totally worth getting to know, so just be his friend and who knows what will happen from there.

6. Act Normal

While keeping everything I’ve said in mind, just remember to be yourself. If you’re an extravert, there’s no way for you to really try and relate to being shy. So, don’t pretend you’re someone you aren’t. They’ll see right through you, and you’ll probably end up having to walk away awkwardly.

Never try acting shy! That’s just insulting. There’s nothing like unintentional mocking to ruin any chance you have with a guy.

Also, even if you tried to act shy, you can’t pretend to be shy indefinitely! It’s impossible! What’s the poor soul going to do when the girl he thought he had already “gotten to know” turns out to be completely different? Have a heart—don’t put him through that.

Opposites do attract. I see them work out all the time. So, don’t let your differences deter you.

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