How To Approach A Shy Guy – When And How To Talk To The Quiet Men

Shy Guy Dog Looking Out Alone

What to do when you find yourself attracted to a "shy guy". How to safely open him up so you can better your chances of connecting with him.

Today's post is filled with tips on how to talk to a guy whose shyness is making it tough on you. This was written as a direct answer to a great question from a dedicated reader who left the question below:

There’s this amazing guy and he is literally all I think about. I really like him but he’s really shy and doesn’t interact with many girls often. I’ve caught him looking at me several times but every time I try to talk to him the conversations are really short.

I’ve made him laugh before but then it seems like he’s avoiding me whenever I see him.

I know his family fairly well and him too, but I don’t know if I should approach him with the idea of being more than friends.

I can’t tell if he’s into me or not and how to approach him if he is.


I used to be a very shy guy so I think I can help you out. First Let's dig into his mind from my previous point of view.

It felt like I was going to be judged negatively. I wasn't sure what to say or how my words would come across to others. I was always "at a loss" of what to talk about and was a little afraid of doing something socially unaccepted.

Although this shyness  was there all the time and I preferred solitude and working alone than with others, when it came time to interacting with girls and then women - THAT is when it was the worst.

Oddly enough - one on one with a woman felt natural. I could be myself. I felt most comfortable and at ease and could connect with anyone.

In a group - even just one extra person EVERYTHING changed and I would retreat to barely interacting or talking to others. Part of that stemmed from a fear of confrontation and part of it came about from an unknown place...

It just never felt right. Like something was a little off. It wasn't a full blown anxiety with a fast heart rate  because I would handle all that nervous energy by tapping my hands on something, rocking my legs, any tick which would alleviate the tension I was experiencing in those moments.

Where my shyness around women came from was obvious - a low self-esteem, insecurity about myself, I felt ugly and believed NO girl or woman would ever want me and so I'd have to make up for it by developing a private friendship first and HOPE something else would happen.

Which it rarely if ever did.

Based on the psychology of shyness and what I experienced it becomes a little more clear on how to approach and talk to a shy quiet guy so he's less likely to continually avoid you in the future.

It's best to start the approach or conversation when there is very little social pressure added on top of what he is already experiencing.

(Nervous, anxious, unsure, and self-conscious.)

In other words make it a very clear ONE on ONE interaction where others can hear what it being said or done. I'm not saying that is easy - merely saying it's the BEST place for it to happen.

Shy people tend to internalize too much and connect it to themselves. If others are around, you won't be talking to him directly - you'll be speaking to the FILTER he puts in place to protect himself making it extremely difficult to connect  with him AND he will do anything and everything to avoid being STUCK in that position.

Since shy people tend to have more social fears they live in the future a lot which is generally where the fear lie - a prediction of a bad event.

This means you must NEVER go into thinking you want to be more than friends with him. Don't add to the pressure - alleviate by keeping it open and very neutral until he begins to feel more comfortable around you and less fearful of screwing something up.

Here's a simple example of how even a simple small question adds pressure.

"What do you do for a living?"

Something which all too commonly asked early on of a guy. You might think it's no big deal to answer but it actually is because:

He might not like his job and is worried you won't like him for what he does. He might not think it's "cool" enough. Even IF he enjoys what he does his first thought is (because he's probably been very unsuccessful with women) that YOU couldn't possibly be attracted to a guy who does THAT.

And that's just a simple career question. Imagine other questions which are far more revealing more intense to answer.

It's BEST to steer clear of personal questions like that. It's tough but it's certainly possible.

Think of it this way: No questions. No pressure.

Your immediate goal  should be about a simple fun exchange of ideas which he feels less likely to be judged on.

Observe something unique. Relate it to something you're used to or have in common with him or let him make that connection himself.

Here's another helpful tip:

People (specifically shy guys) FEED off the energy around them so much they FEEL it more than others.

Which is just one reason shy guys avoid public places that are high energy. It raises their self-conscious thoughts to a higher level.

This means YOU must do whatever you can to avoid being nervous yourself. You must quiet your mind and your body language. So you BRING him to a state of complete by being at complete ease yourself.

I'm not saying you have to do it perfectly - just to understand how important it can be and how when your mind is racing forward and your energy level is higher than usual - it will rub off on him.

Making him for one - more nervous and you'll make less of a connection with him AND once again - he'll do anything to avoid being what he feels is STUCK in a situation he can't easily get out or remove himself from quickly.

Here's a great post I like to help you achieve that from Mirabelle Summers:

"A common mistake that intelligent women often commit is to think too much about certain things. They get so caught up in their own world of thoughts that they’ll come off as aloof or distracted… when in reality they’re just petrified from FEAR of not knowing what to say next."

Communication and Conversation Tips – How to Talk To Men

Another few tips:

Take things SLOW. slower than you normally would for a guy who isn't so shy and reserved.

Add a little self-deprecating humor to the conversation. Chances are - if he's attracted to you he's going to put you on a pedestal which is only going to push him away or have him do things which are far from attractive and he's subconsciously is aware of it.

The more "goddess" like he thinks you are - the more introverted and uneasy he will feel.

You will take off some of the pressure on him, make him feel more relaxed and open around you, AND more safe.

When a shy guy feels that way around you - he will be FAR more likely to want to experience it again and again and again.

When he feels safe - he'll open up and you'll find connecting with him a lot easier an natural too.

Now that I've got some of the tips on talking and opening up a shy guy - let's dig a little further into what you wrote before this is finished:

He's an amazing guy who is always on your mind and you're not sure if he likes you; I'm guessing you mean "in that way".

Of course he's amazing - why else would you be thinking about him all the time.

Here's something you must never forget.

ALWAYS assume unless otherwise directed, told, or shown that a guy can and should be interested in you for something more.

I'm not saying that you must believe all guys want to get in your pants and act in that way - that's the extreme and bad opposite.

I'm merely saying that you must feel and believe you're confident and beyond good enough to be with ANY guy you choose.

Don't approach it with, "I hope he likes me?????"

Approach ALL potential dates with confidence and a true belief in yourself and go from there.

You've caught him looking at you a few times but when you've tried to talk to him the conversations are short.

Since I'm not there listening to the conversation or watching him stare at you - I can say neither one way or another why the conversations are short.

It could be that's he's shy.

It could be you or him or both of you are not generally good at talking to someone in a certain way when you're attracted to each other.

BUT if you believe he's "checking you out" - then go with it and do what you can (based on the tips above) to keep the conversation as light and fun as possible AND introduce some real FLIRTING with him.

Don't WAIT for something to happen. MAKE it happen. Just make sure you're sticking to the female side and not being too pushy or masculine and I'm sure you'll do just fine with it.

You've made him laugh but it seems like he's avoiding you.

Okay - making him laugh is  good thing but honestly, doesn't really mean much here. Guys like women with a sense of humor but when it comes to attraction - there MUST be a lot more to it and a lot more going on.

Not that it's a bad thing - just don't go reading too much into it.

Now if he's avoiding AND you absolutely think it's because he's shy - then don't worry about it.

IF it is a problem AND the tips above are not working AND you're finding no way to get through to him then I'm sorry BUT that is his issue to deal with in his own way.

REMEMBER: It's a BIG responsibility of him to be a man here if he's interested and attracted to you.

If he won't or can't - there's not much more you can safely do without taking on the masculine role which will either cause major problems in the future or send him running.

You're not sure if you should "approach" him with the idea of being more than friends.

Find a balance which works for you.

It's not always best to go into it with the IDEA of being more than friends BUT at the same time you don't want to go in it with the sole purpose of getting a date.

Which means - you need to leave it OPEN to going somewhere BUT at the same time make it more probable to happen.

It's a bit tricky but not impossible.

What I teach guys you can use too...

Don't go into ANY interaction with potential date to GET something - do it to give something. Something memorable. Something fun. Anything which makes them WANT to see you see again.

Don't add all the unneeded pressure of getting a date because you'll act outside your attractive self and quite honestly - whenever you sense someone is TRYING to get something from you - you're far less likely to get it.

Rather than getting into all that because it's kind of a big subject, I'd like you to read this next article that I love to turn to because it's so good... from the same woman in the article above.

It's about "dates" in general but the idea of staying in the moment do APPLY here and should be used in each and every interaction you have with guy SPECIFICALLY when you're INTO him this much:

"And because of the importance that you’ve invested this date with – the emotional significance that it now has for you, what with this guy potentially being your future husband and all – suddenly, everything is MUCH too important for you to be able to relax.

There’s too much at stake.

What if you screw up?

You’ll have ruined a potentially great relationship with this guy, who could even be The One!

What if he doesn’t like you?

What if you do or say something dumb? What if you RUIN everything??

That is the kind of thinking that your ‘mental chatterbox’ will subject you to, when you over-invest in an event’s significance. The pressure involved causes you to get stressed out, anxious, self-conscious, and jumpy …

… and it’s simply NOT ATTRACTIVE."

The Secret Trick To Great Dates – Get Out Of Your Head & Into His Heart

The original author is part of a team of experts on dating, attraction, and relationships called Meet Your Sweet. That's their main link. They give me this one to point you to where you pick up the extremely helpful Get A Guy Guide - Leading you with a video: Powerful Obsession Triggers That Make Men Crave You.

Whereas I tend to specialize in understanding men and all that good stuff - advice like you've been given today is a little rare for me. You can, with certain, benefit from checking out those few links above to help you ATTRACT and CONNECT with ANY men - shy or not.

Lots of great advice there.

In conclusion...

The "shy guy" does require a little more tact or a slightly more reserved approach if you want him to STEP up, OUT OF HIS SHYNESS and take you out for a date or to assure you're seen as more than a friend to him.

Try to keep it one on one (f possible) with him so he'll be less reserved.

Cut down on as much as you can on the added social pressure shy guys feel.

Stay away from asking too many personal questions about him. Let him reveal himself to you slowly and on his own terms so he'll be less likely to retreat and avoid seeing you again.

Keep it all simple - go in it with the idea of just exchanging fun stuff that you both can relate to.

DO your best to make sure if you're nervous or have a little extra energy that's it's not too obvious - your state of mind or being will rub off on him. If he feels it too much with you, he'll be far less likely to want to be put in that position again.

Don't sell yourself at all. If he already has you on a pedestal you don't want to make it worse because you won't get himself, you'll get a huge filter and find it extremely tough to open him up and connect with him.

Try some self-deprecating FUN humor or anything which eases hie view of you. It won't affect his attraction or interest in you.

Follow the tips from Mirabelle above - they'll help you quite your mind and his at the same time AND they're just great advice anyways.

I used to be a shy guy myself so I know where's he's coming from - a little insecure, low self-esteem especially around women, fear of social pressures or saying or doing the wrong things, a feeling like we're always being judged, and WAY too many self-conscious thoughts which has us living in our heads a lot more than usual.

Keep all the in mind as you approach the shy guy BUT never forget the reality of guys like this:

Some guys like this will NEVER let you in.

You can do some encouraging things to open him up and get him to feel more comfortable around you BUT...

The rest is HIS deal. You're not there to CHANGE him.

You want to avoid taking on a masculine role when you're with him because that will pose future problems which are easy to predict because they WILL happen.

It's ENTIRELY HIS responsibility to get past all this shyness and fears so don't waste too much of your valuable time IF it's not working for you.

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This article was posted in How To Get His Attention, Gain His Interest, & Attract The Right Guy

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19 comments… add one
  • Laura

    There’s a guy in work… we had never really met before as we work in different offices in different cities, then, when I was visiting his office, we went to after work drinks a couple of weeks ago. We spoke and drank together for at least 3 hours, and he told me all about his background, he asked how often I’m in his office, we laughed etc… He came to my office last week, and didn’t say a word to me. Barely looked at me. After work, a few of us went for drinks. A mutual friend asked if there was anything there, and I said that I wasn’t at all sure because there had been zero interaction since the initial chat. He told me to just say hi. The next day I had to ask him something about work. He replied to my initial message, but not my next one. Yesterday, he was in my office. We didn’t have any contact, just occassional shared looks. Then we were passing each other so said hi, and I asked him a favour, which he agreed to do for me. Then, we had snacks that I shared around my team, including to him as he was sitting near by. He said thank you. Today, I messaged him to thank you for doing the favour. He didn’t reply. I’m a bit confused, is he shy/not interested?
    I just don’t want to force anything on him, but it’d be nice to have a clue about how he’s thinking/feeling.

  • Pink1234

    Hi thanks and am not obsessed with it lol just confessed that’s all and part of it because I did like him for year never thought he would be interested in me thought he was too good looking for me and when I did notice him staring it kind a put a smile on my face just wish for once I can get a guy I like

  • Pink1234

    Thanks and sorry for all those comments ur the only one who makes sense other just tell me to just pass him my number whe n he didnt want it when I asked him. It kinda is getting uncomfortable because I have got a clue what he’s all about . I guess part of me is hoping he will ask me out or even say hi or some thing I can’t never fighter guys out hopeless . Now he’s too scare to even look at me . Should I apologise for bitting his head off I feel bad for saying that to him .was I benign rude ?

    • Peter White

      Honestly, I wouldn’t worry about it. People can be generally rude a lot whether they mean to be or not. Some people can even be more rude to people they like.

      Just be done with it. Start over with someone else as quickly as you can.

      You don’t need to figure guys out, it’s not necessary. Maybe helpful at time but not necessary. 🙂

      You went out of your way to meet someone and it didn’t work out. Doesn’t mean you stop doing it. Do it again to another guy and see how that goes. You might be surprised.

      If it keeps leading to the same outcome THEN it’s time to change it up. One bad interaction doesn’t mean you blame yourself or let yourself feel helpless.

      Move on. Try it on other guys immediately. When a failing pattern emerges, like give it at least a round five attempts and if it’s not working, then try something else. You’ll get it eventually.

  • Pink1234

    I do like the guy have for years . But when I notice him staring it kinda made me happy to think he liked me too but he never spoke or try to speak to me once it’s always been me who made the first move . Guess it’s just annoying the fact that why would he do all that if he didn’t have any interest in doing any thing about it or didn’t want anything out of it ?

  • Pink1234

    Thank you but I think I kind of mess that bit up got on the bus he was on when I went to put the fare in the box I cough him smiling so it kinda a pee me off after he made me look like a fool so when I got off first I asked him his name which he reply back then he asked for my name which I told him then I told him to stop smiling that he already made me look like a fool his reply back was am I not loud to smile now . It’s just confusing he stares but when am talking to him he never looks at me once always looking the other way . Was he interested in me or is he just one of those guys who likes to mess around ? Should I just avoid him now don’t want to make more a fool out of myself ?

    • Peter White

      You’re welcome. I think you’re both past the staring thing and you’re becoming more obsessed with that part and forgetting the rest of it.

      He’s teasing you. Whether it’s messing around with you in a bad way is not something I would know from my point of view.

      If it’s making you this uncomfortable and you can’t get past this, then I’d say for that reason alone I would avoid any more interactions with him for a while.

  • Pink1234

    I see him drive by me most of the time either he turn away and looks the other way or I do . How can make this stop he’s know now that I like him and I kinda miss our we stare off . Should I talk to him ? And I get the feeling he liked me too that was the only reason I asked him . Like just last week I was walking round the corna and there he was and our eyes just met I tried not to look at him but I could feel him staring at me and I turn around and he was so we had a stare off once again for a few sec . One of those stare where every thing around u just stops . Is it all in my head because I was pretty sure he felt the same way and that he’s lying about staring at everyone like that because I have seen him around for years and I use to always look at him when he drove pass but he never notice he never use to look around at all . What should I do

    • Peter White

      You could keep building this all in your head or you could start talking to him. Some people take a while to open up for reasons I’m not getting into.

      Your conversation must not be about this “staring contest”, your feelings, or anything like that.

      Just open a normal conversation. That’s all “Pinky”.

      If you insist on the staring thing with him or want to use his “I stare at everybody” thing then use it positively… “What do you learn from people you see everyday?” “Do you like watching because you enjoy the social complexities?”

      Tap into his “obvious” attraction to watching people. Remember, it’s his job to see lots of people everyday and he just might be totally interested in it. So use it.

  • Pink1234

    Hi a fews weeks ago I notice guy who is local bus driver I see him almost every day I caught him staring at me a few times and he doesn’t turn away when I caught him staring infact we have like a stare off every time we see each other . As I liked the guy and I thought he liked me too I build up the courage to ask him but he turned around and said no ? Now I feel like a fool and see him driven by every day what do I do ?

    • Peter White

      What did you ask him?

      • Pink1234

        I asked him if he was single .he said yes and then I asked him if he wanted my number and he said no then I said to him what’s with the staring he said he stares at everyone like that . Where did I go wrong as this was the first time I ever asked a guy out

        • Peter White

          I would avoid asking a guy if he’s single as a conversation starter. I also would never ask a guy if he wants your number. There are more “clever”, fun and flirty ways to get that kind of information which can lead to something more advisable… exchanging contact information.

          Besides that… you met a guy who stares at everyone and drives a bus. He’s a people watcher. I wouldn’t take it too personal at all.

          Who knows, maybe he’s just a strange fellow. 🙂

          Next time you want to approach a guy, use this experience. Just smile and say “hello” Take something from your surroundings and keep the conversation in context from where you are. Avoid what you did here and just be open to letting the guy take the lead.

          Don’t let this courageous act stop you from trying again. Just change your tactics, that’s all. Failure is not a reason to stop, just a clue to try something different.


  • Morgan

    I need some advise please , there is this guy at my child’s school that I am really interested in . Unfortunately we are both shy and just exchanged glances over weeks . I finally brought myself to start a conversation and he engaged and seemed happy to talk to me . But the next day he would just keep looking at me and we exchanged lots of smiles , but neither one of us started a conversation . Where should I go from here

    • Peter White

      Well Morgan I DO hope he is a teacher and not still in school. 🙂

      I would just find some lame excuses to talk to him and make it fun.Be a little flirty.

      Sure some guys see past the “lame excuse” routine and will assume you’re “hitting” on them but there are many, many guys who will only see it as a friendly gesture. Another reason to be flirty.

      The idea is to come up with some excuse and tie it in to something funny he can relate to. That’s all. Don’t make it out to be a big deal and you’ll be just fine. There are so many thing to pull from in school like homework, teachers, how bad of a student you were, how the principal is always giving you a hard time, which kid annoys you the most, which child keep hitting on you, etc…

      I think you’re getting the picture here Morgan.

      You started one before so do it again except this time, throw in some flirty humor, make some very casual contact with him like slapping his arm or even shaking his hand, and see where it takes you. Don’t read too much into the interaction and stay in the moment.

      You’ll be fine.


  • Jen

    Dear Pete,

    Around 1 year ago, I met a guy. He was obviously interested in me but never have the guts to start a conversation. He can stare at me confidently for a solid 5 second if he expect to see me at a certain place but if I appear near him unexpectedly he would be so nervous. I was waiting for him to approach me he did try but mostly lost of words and end up freezing up. The worst thing is he left the company.
    I knew I liked him so I begin to search him out but it was difficult until recently I got his number so I texted him. He say he did not remember me so I told him I might get the wrong guy then. Few days later, he blocked me on what’s app. So should I move on or ? Because I don’t expect such a huge reaction from him … I mean if he did not remember me he would not blocked me. What should I do? If he had move on or even had a gf (his fb status is single) he should be quite chill about it?

    • Peter White


      If he’s being this much of a bother, I would definitely move on. It appears, based on what you wrote, that he has serious issues when it comes to interacting socially and/or he’s just not as interested as he might have appeared to be.

      Why waste your time with a guy who isn’t at least pleasant and doesn’t even remember you.


  • Emma Kelly

    PLEASE READ!!! HELP! I think I’m interested in this really, REALLY shy guy. About 2 months ago he handed me a the school newspaper and didn’t really look at me. With my stupidity I took this opportunity to message him on IG “Hey I think you gave me a newspaper last period and just wanted to say that you’re really cute(:” he looked at it and never answered. About 3 weeks pass and I started smiling at him whenever I saw him. He would see me smile, get a bit red and look down immediately and THEN smile. Like he meant to smile at me but didn’t want to make eye contact. So I then tried to take the opportunity to message him again and say “Hey (:” again, he looked at it and didn’t reply. When I pass him, some times in the corner of my eye I’ll see him look at me for a quick second. How do I approach this guy and introduce myself in person to maybe become friends with him. I’m scared I have ready made a fool out of myself by messaging him and he thinks I’m a total freak ): PLEASE HELP!!

    • Peter White

      The truth is Emma, he doesn’t think you’re a freak. He’s probably pretty flattered by it BUT if he isn’t attracted to you then things might become a little difficult for him to respond to you.

      The cards, or your feelings, are all out on the table now. He knows you’re interested. The fact he hasn’t done anything is unfortunately a bad sign. I mean it doesn’t take much for a guy to just text you back, right?

      My suggestion, so you’re not wasting anymore time, or you don’t find yourself falling deeper for this guy is to, and you’re going to hate this, Just say “HEllo” and start talking to him about something you might have in common.

      Trust me. There’s no secret approach or line you can use on him… well if you must read my funny article on pick up lines for women here:

      If you can make a friend, you can talk to him. You just need to change the dynamic of the conversation or interaction so you’re not coming off as just a friend right away.

      Play to your strengths. Play up the fact you think you made a fool of yourself. Guys actually like women who don’t take themselves so seriously.

      No more messages UNTIL you have a face to face conversation and I’m sure you’ll have it all figured out right after the first one.

      Best of luck,


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