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

in Stare and Approach
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When you find yourself attracted to a “shy guy” or interested enough to want to get to know him but you’re not sure on how to approach situation…

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.

Hello Cat,

I wouldn’t suggest approaching anyone with the idea of being “more than friends” put out there.

It’s best (in my opinion) to play it neutral at first and let the moment develop naturally. This also alleviates much of the pressure in these kind of situations which sometimes makes us, in the very least look needy, desperate, controlling, or things which can deter attraction.

Never “sell” an early interaction too far into the future.

So many people are shy, at least from my view, because they’re afraid of the future. Socially speaking of course. They either try too hard or don’t try at all making things perpetually uneasy for them.

If you approach a shy person and apply social pressure, you can get some pretty strange results because they tend to internalize too much of what is going on and connect it to themselves.

When I was shy it felt like I was always being judged negatively. Like I was eventually going to do or say something wrong or socially unacceptable.

While interacting with the girls I was attracted to, I was putting on an act. I was monitoring my every thought or action to avoid doing something wrong. Women never got to talk to the real me in those situations.

Doing something wrong in those cases meant she wouldn’t like me or it was the reason she wasn’t attracted to me when I was rejected.

That’s the internal connection. It’s a  limited belief system of a shy guy. ( Based on my observations of men and past shyness.)

Since then though, I’ve learned the mystery of it, maybe she likes me, maybe she doesn’t, creates a far better experience. Kind of like a “let’s have fun and see what happens” attitude.

That’s the attitude you can have when you do approach a shy guy, or when a guy approaches a woman whether she’s shy or not.

A little self-deprecating humor also helps because it alleviates stress.

It’s easier to be who we are when we don’t take things like just having a conversation so seriously. It should be an energetic exchange of ideas, wit, and humor practically devoid of most questions.

An example would be:

Bad question with pressure attached –> “What do you do for a living?” A shy response would have the guy (or person) thinking you might not like him for his job. Or maybe he’s not that passionate about it or doesn’t think it’s cool. Remember they internalize more when they’re talking to someone they’re attracted to. ( Explained as being overly self-conscious. )

A better idea without pressure would be –> “Amazing. You look like you work-out for a living. I have my good days and bad days but then again – I can be a little lazy. Haha!”

No questions. No pressure. Just a fun exchange of ideas.

Observe something unique. Relate it to something you’re used to or have in common. Bust your ass own a little ( Light-heartedly of course ).

Work in the flirting slowly if the chemistry happens to be there and is definitely building.

Shy guys NEED social safety before they open up. They despise, avoid, or act differently when they’re in situations which could lead to a judgement or their character or a social disaster.

“Shy guys open up easier when it’s socially safer. They work better one on one or in very small well-known social groups.”

Imagine something I’ve experienced many times in my past…

Here’s this new attractive co-worker and I was in luck, we met and started talking. No one is around and everything feels fun and easy. Like I could be myself.

But, as soon as one other person enters the group discussion the energy changes. It feels different. It adds pressure.

Suddenly I found myself time after time not acting like I was the minute before. I bow out of the conversation gracefully (or disappear) usually with some pre-planned excuse.

It no longer felt socially safe. My brain would switch over and I’d become much more self-conscious.

After something like that would happen the only time I would then come around is when she was alone. I might stare and wait for the moment to appear. Trying to look busy or like I didn’t care. Yet I’d be not so patiently waiting for “alone” time to come again so I pick up where I left off with her.

I know – us shy guys… aren’t we just so adorable Cat. 😀

You can approach a shy guy in a group. He’ll even deal with some larger social areas but rarely will you ever get any more than his persona if it’s too publicly.

Again, their self-conscious thoughts causes them to monitor their thoughts and action more because they’re worried how others might judge it.

“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.”


Both men AND women can easily have their self-conscious thoughts creep in and possibly deflate an otherwise great connection.

Advice on approach or those first meetings doesn’t seem to change no matter who we’re talking to.

If he’s shy, then again it’s best to be one on one but the supposed rules are no different to enjoying a “stimulating” conversation.

I believe Miralbelle Sommers did a great job on how to talk to any guy and how to quiet YOUR mind too, if that’s a problem.

Shy guys will feed off your quiet mind and are more likely to follow your lead. Give it a read – you might find some better pointers in it rather than me just repeating her words. You’ll find the link to the full article there at…”The Approach” That’s my side “gig” I rarely pay attention to. Haha!

You’ll find it above or just click here: Conversation Tips: How To Talk To Men

Approaching, talking, meeting, whatever it is – I do hope another shy guy doesn’t pass you or any other woman by just because he’s a little socially withdrawn and you were not sure on how to handle it.

I’m pretty sure there are some great guys out there who tend to stay a little quiet and just might need a push in the right direction.

Hopefully the course I’ve laid out gets things heading in the right direction for you Cat, and everyone who is passing by.

If anything, it does help to understand how shy guys think and the purpose of this was to give a better look inside “this” guy’s head.

About the author: Peter White… Showing men and women ways to attract each other naturally by helping you to understand each other. Over ten years experience which has shown me how to see things clearly and get to the root cause of most dating and relationships problems. Hope you learn and enjoy your why do guys experience.

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19 comments… add one
  • 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: http://www.dialteg.org/dont-wait-for-him-approach-you-pick-up-lines-for-women/

      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,


  • 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.


  • 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.


  • 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.


  • 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

    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 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

    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

    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

  • 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.

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