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 f@&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.]



  1. Kimberly Esther says:

    I've been dying to ask this question, but I didn't know how to put it into words. After watching the film I wanted to hate the book but it seemed to make so much sense. If a guy really likes you, then wouldn't be make a move? It just confused me so much. Anyway thanks so much for this answer, it makes guys seem a lot more human then the book.

  2. jessie says:

    I feel like guys can be the same as girls if not worse with the whole scared of rejection thing. maybe he's just not sure if she's into him yet.. if that's the case, he'd probably ask her out if he knew she was interested.

  3. Alberto says:

    The Shy Guy lacks in confidence, but he also tends to be more faithful.

    1. Iokobos says:

      There is a fine line between faithful and doormat.

    2. jack says:

      No, not at all. It's more like a well-defined, though not necessarily visible, boundary. Kinda like mowing my lawn, I'll be damned if I'm going to do my neighbor's work for him, I don't care that there's no fence.

  4. @twymx says:

    Honestly, don't botther at ALL with shy guys. They have weak sperm! Go for the confident guys. Yeah they might cheat and probably will. But jesus, the pussification of the american male continues! Do NOT baby these shy guys, because they will just stay shy and you will eventually get bored with them! But seriously….do NOT try to rope one of these pussies. They will be the types that will always be saying to you "I don't know….what do YOU want to do?" Uggg. So basically you handle a shy guy by saying "buh bye"

    1. Mr. Bumpers says:

      Well I guess I fell into the category of "shy guy" not a "pussy" or a doormat just kind of naturally shy. Finally met the right woman though, and we've been happily married for thirty years. That three zero years. As in 30. So screw you.

    2. SoConfused31 says:

      Mr. Bumpers: How did u end up dating? did u ask her, or she asked you?

  5. Dominique says:

    First of all, love love LOVE this column!
    This is basically the same as a guy wondering if a girl is sending him "mixed signals" because she seems happy to see him but never seeks him out. I hate how people think it's cute when a girl is shy but a shy guy is so outlandish to them. Let's bring ourselves out of the 50's and try to remember that guys have feelings and varying personalities as well. Just like all women aren't fearless dominatrices, not all men are outgoing skirt chasers. :)

  6. […] as H-E-double hockey sticks (for further reading on shy guys check out last week’s column: How Do I Handle A Shy Guy?).  I doubt you’ve sabotaged yourself. After all, he did take you home, twice. Plus he […]

  7. Commentor says:

    Think of a totally old fat guy walking up to a young lady and getting too close, talking to her, pestering her. There was a scene in A Room with a View, where Helen Bonham Carter tries to go to the museum alone and the Italian would not stop bothering her. [It is not illegal to keep at it way past politeness.]

    They regard women as objects and so treat them like furniture (that's on the good side of this attitude) or worse like sheep (obey or get a beating). So, thus, we shy guys are leaving these wonderful women to suffer these borderline or actual prison thugs who however briefly are assertive, charming, and attractive, but who are really obnoxious.

    I'll try to be less of a wuss.

  8. OMG says:

    This is one of the dumbest "advice" ever. There could be ton of reasons why he doesn't seek you out. He could be busy with work. Maybe he's already interested in some other girl. Maybe he doesn't find you attractive. Maybe he thinks "we should hang out later" is just a thing people say (and it is, isn't it?). Whatever the case is, please stop trying to fit people into groups. If you like the dude, why don't you go talk to him and make it sort of obvious that you're into him.

  9. Mike says:

    I think a lot of people, including this Dude guy, confuse introversion and shyness. Introverts just have a weak motivation for being with others whereas shyness means they have feelings of tension and discomfort. Not all introverts are shy.

    Admittedly, I was that shy wuss. I overcame that in the summer of '09 after working on it for year. Working as a lifeguard that summer had a lot to do with that as well, it forced me to become real assertive. I am still introverted though, and after a while of socializing in a group of people I'm just drained.

    To those shy guys reading, you need to become assertive. If you don't people will continue to walk all over you. The summer of '09 happened to be after my sophomore year of college. In my first two years at school three great women pretty much threw themselves at me, but because I was a shy wuss nothing ever happened. One of those woman was a perfect match, personality wise she had everything, she was beautiful. I haven't seen any of them since I was reborn but I think they would have moved on regardless, can't blame them.

    Point is those opportunities don't come around often. I knew when I was a shy wuss I wasn't living life. I'm now a senior, and an electrical engineering and physics major. My senior thesis and project take up all of my time. My classes have been all male since I was sophomore at a school that is 62% female. I went to an all-male school from 6th grade through the end of high school. I have two brothers. The next time I will be near a women my age I will probably be socially nieve/somewhat clueless if there's any flirting, but I'd rather get rejected then not do anything again. Breaking out of that shell saved my life.

  • You Might Like