Ask A Dude: How Do I Handle a Shy Guy?

Hi Dude,

I just wanted to know what your thoughts are on the whole ‘He’s Just Not That Into You’ phenomenon. I should start by saying that I’ve read the book, and a lot of what it says makes sense in theory… But, here’s the thing: There is this guy at work that I’ve only bumped into like 3 or 4 times, but he’s really cute and we seem to have fun talking to each other.

He’s always really nice, and he’s complimented me once or twice. He remembered my name after the first time he met me even though it was a few weeks before he saw me again. But…one time when he was talking about how he’s always out and around the building, I told him he should come visit me some time and he never did. I decided to go visit him a few weeks later. He seemed happy to see me, but had to go to a meeting. There hasn’t been anything since.

Sidenote: There has been one or two signs that make me think he may be interested, but he has never actually asked me out. The ‘He’s Just Not That Into You’ guy says that there is no ‘shy’ guy, that if he actually liked you he would have asked you out by now. Is this true?


Dear Ali,

First of all, it’s a pleasure to respond to someone with a name that sounds vaguely human.

Secondly, I’ve never read He’s Just Not That Into You. So, I can’t really speak to the sociological validity of that text’s theories based on my own experiences. Jargon out of the way, let me pontificate: The Shy Guy Exists! (In Morpheus’ baritone from the scene inside the caves of Zion in The Matrix: Reloaded)

I’ve been a shy guy. I know shy guys. I’ve been frenemies with shy guys. They’re out there and they’re [email protected]&king frustrating!

Shy guys are…pussies. Up to a point. Hey, I’m going to get a ton of hate from the shy guy community for saying this but they won’t use their real names when bashing me…which proves me right.

Shy guys avoid confrontation at all costs. Not because they’re pacifists. They’re scared of getting hurt, humiliated, and being embarrassed. Their default mode is one of self-consciousness. Shyness then becomes a self-perpetuating condition because they become ashamed of NOT being able to come out of their shell which drives them further inward. So, in the sense that they’re scared to put themselves out there, they’re pussies. Doesn’t make them bad people. Doesn’t mean they have to stay that way or that you can’t help them reach out. It just means they’re pussies.

That being said, there are tons of ways for shy guys to achieve higher functioning and greater levels of self-esteem…but that’s for another day. What you need to do is take the initiative and then decide, based on whether he responds or not, whether to move on or try again.

Since the shy guy avoids confrontation, including romantic ones, you’ve got to take the lead. Be the one to make the first move. It’ll show you’ve got confidence and there is nothing sexier than confidence. You’ll take control of the situation rather than letting the situation control you (which generally puts one in a state of torture). And lest we forget, you stepping up and taking the lead will actually end the will he/won’t he madness.  All it takes is someone actually taking a the definitive first step and who knows…Chuck Bartowski and Sarah Walker, anyone? Anybody?

If you do that and he doesn’t show signs of life, consider the whole thing flat lined. Then, take another lap around the talent pool.

Go for the gold,
Dude Phelps

[Isn’t he wise? Don’t you wish you could get more? You can! Check out The Dude’s other insights into the male mind right here.]

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