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Dating: How To Approach a Shy Guy

Credit: Flickr/ Eddy Pula

You’re into him, but how do you approach him?

I was watching ‘The Today Show‘ this morning and Willie Geist was sharing tips from his article in this month’s issue of Glamour, ‘5 Ways to Get a Shy Guy Talking.’

The more I was watching, the more I realized that I am that quiet guy, and most of these would work on me.

So, if you’re into a shy guy, and you’re not sure how to approach him, I guarantee these tips that Willie gave out will work. I’m not saying he will fall in love with you, but you will at least get him talking.


1. Approach him aloneĀ 

If you follow ANY rule on this list, let this be it!

There is nothing more terrifying to a shy guy than a pack of women approaching a him when he is already feeling uncomfortable. I’m not saying we’re weirdos, we’re normal, we just don’t warm up to situations as quickly as an extrovert. We’re typically total open books around people we know, we just clam up around people we don’t, especially a group of women!

Note: Only approach in a group if he is standing in a group.


2. Use a Funny Confident Opening Line

For example; as Willie puts it, if he’s playing on his phone, a good line would be, “You beat your high score on Candy Crush yet?” It’s sarcastic, but funny. Any guy would appreciate that, it warms up the situation big time.


3. Get Intel from His Friends

I’m not too big on this one, because I think it can come off really fake. They’re saying you might want to find out what he’s into, like sports or whatever.


4. Find a Common Enemy

This is the 2014 way of talking about the weather to get a conversation going. Maybe the bartender is slow, maybe the DJ is playing horrible music, now you have someone you can both pick on. This would get him talking but it could be, “that DJ is my best friend.”


5. Pretend You Recognize Him

This is Willie’s final piece of advice, yeah it’s a fib but it will get conversation going

Being THAT GUY, if you spot a someone like this that you want to approach I would advise you to approach him, because he won’t approach you.

Are we wusses? No. We’re actually pretty nice people, who know how to have great conversation. That leads me to this next piece of advice, if you approach a shy guy and he still won’t talk when you try to engage him in conversation, move on. We typically open up pretty quick.

Here’s the clip from ‘Today.’

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