How to Talk to a Guy if You Are Extremely Shy

Three Parts:Approaching HimRethinking Your ShynessContinuing to Talk

There’s a guy that you want to talk to, but you’re shy and can’t figure out exactly how to approach him. You’re not alone – this is a normal feeling. There are techniques that you can use to boost your confidence, to find a way to approach him, and to start a conversation with him once you’ve said hello.

Part 1
Approaching Him

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    Consider the setting. You typically see this guy at the same place – maybe work, or at the library, or perhaps at the subway station. Think about the time of day you see him and where you see him, as this may have some bearing on how you approach him. If it’s really loud, for example, you might need to plan a way to get his subtly get his attention before you approach him.
    • If you see him pretty regularly at the bus stop, for example, your approach will be different than if you see him somewhere less public and quieter, such as the school library.
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    Smile at him. Because we’re human, we put a lot of stock, knowingly or not, in body language (kinesics). Guys notice smiles, and you’ve got one to share. A smile tells him a few things about you before he ever talks with you: it tells him that you’re not a snob or aloof, that you are enjoying your day, and that you’re a positive person.[1] We are naturally attracted to happy people, so next time you see him, even if you don’t approach him, make sure to smile.
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    Make eye contact. If you’re not quite comfortable walking up to this guy and talking to him yet, you can still get his attention by making eye contact. Or, if you catch him looking at you, hold his gaze briefly. Whether you initiate the eye contact or he does, hold the gaze for a second or two and then look away. You don’t want to run the risk of appearing creepy by maintaining eye contact for a long time – just long enough to let him know that you see him.[2]
    • This is another great opportunity to smile a little at him.
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    Ask him a question. When you’re ready, walk up and simply ask the guy a question. It shows him that you’re interested in his answer, and once you’ve broken the ice, the way is clear to keep up the conversation.[3][4]
    • “Hi, I see that you have the wireless version of those headphones and I’m having trouble deciding between the wireless or studio version. Do you like those? Can you tell me a bit about your experience with them?”
    • Hi there, I noticed that your bag says NYU on it, and I’ve thinking of applying there. Could you tell me a little bit about the campus? How about the administration?”
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    Ask for help. Almost everyone likes to be helpful, and this is a great way to open up a dialogue between the two of you. You’re interested in talking to him, so you’ve probably noticed some things about him, such as the bag that he carries with the school or work logo, or the technology that he uses, or that he seems to know the area pretty well. It might seem a bit clichéd, but that’s because it works, and even if you don’t truly need help, this gives you a great reason to talk with him.
    • You could ask him, “Excuse me, can you please tell me how to get to XYZ Bookstore?”
    • Or, “Hi, do you know the password for the wifi connection here?”
    • Or even something simple, such as, “Hi, could you please tell me the time?”
    • No matter what sort of assistance you ask for, make sure that you follow up with a sincere thank you and a smile, and remember that you just opened up the path to more conversation.
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    Say hello. Simply walk by him and say hello, and even smile if you feel like it. You don’t have to say anything more than that, but you certainly can. At the minimum, saying hello lets him know that you’ve noticed him and that you’re interested in talking to him. It puts you on his radar. You might say hello every time you see him for a month before you work up the courage to say something more, and that’s perfectly fine.[5] #Introduce yourself. You might expand on your hello and say something like, “Hi, my name is ________. What shall I call you?” This is a no-nonsense way and deceptively simple way of talking to a guy that you’re interested in, even if you’re extremely shy. You might feel anxious or nervous and that’s okay. You’re not asking him on a date right now, you’re just striking up a conversation and getting to know one another’s names.[6]
    • From here you can implement some of the other techniques, such as asking a question or giving a compliment.
    • Just breathe. You’re shy and you’re probably a bit anxious at the thought of approaching him. You’ve considered a variety of ways to get over there and talk with him, mulling over the pros and cons, but you still haven’t approached him. You might feel conflicted as the internal battle of should I or shouldn’t I rages within you. Take a few deep breaths, remind yourself that you’re in control of this interaction, and decide which method will work best for you.

Part 2
Rethinking Your Shyness

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    Practice approaching others. You’re extremely shy and the idea of talking with people you don’t know can be scary, especially if you think about initiating the conversation. Unfortunately, you can get into a cycle of staying home to avoid talking with others, but that only breeds more shyness. Talking with people is a skill, and just like with any skill you learn, it can be difficult at first, but will get easier with practice.[7]
    • Practicing with other people will help you overcome some of your shyness and should make approaching the guy you’re interested in a little easier.[8]
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    Understand that you can learn from everyone. Every person that you come in contact with has the potential to teach you something. Overall, people like to talk with others and appreciate the genuine interaction with others. Instead of keeping to yourself at the bus stop or waiting in line, next time strike up a conversation with the person next to you.[9]
    • You never know, you might make a business contact, or a new friend, or just brighten someone else’s day.
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    Accept rudeness and rejection. It’s not typical, but sometimes someone will reject your attempt to say hello, or, worse yet, be rude about it. This behavior doesn’t reflect anything about you and you shouldn’t take it personally. They might be having a particularly bad or stressful day and not be thinking how their actions impact others. Just brush it off and try again.[10]
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    Compliment people and go. You want to talk to a guy but you’re shy, and you need to reframe that shyness. One important technique is to approach people and talk with them. As with anything, the more you do it, the easier it gets. A great, no-risk way to talk to people is to give them a compliment and walk away. In doing so, you’re approaching a stranger and interacting with them, you’re showing them that you’ve noticed something about them, you’re complimenting them, and then you’re walking away, letting them know that you don’t expect anything in return, but are fully in control of the exchange.[11]
    • For example, you might compliment their outfit, their smile, their bag, their nail polish, or even their travel mug from a destination that you also enjoy.
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    Compliment people and stay. Ultimately, you want to work up to giving a compliment and asking a follow-up question, such as, “Your dog is has gorgeous eyes! What breed is she?” Now you’re not only letting someone know that they’re compliment worthy, but that they’re interesting enough to talk with. This is a simple but very effective way to strike up a conversation with someone and help you get over your shyness.[12]

Part 3
Continuing to Talk

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    Circle back around. Each of these techniques work nicely with one another, and after you’ve approached this guy and started up a conversation, you’ll want to talk more, or again at a different time. So stack these techniques in the way that feels most comfortable, and keep the conversation going or use them the next time you talk.
    • If you say hello or introduce yourself and would like to talk more, follow up with a question. For example, “Hi, my name is _________, and you are? I’ve noticed that you come to this coffee shop a lot, can you recommend an espresso drink?”
    • Or you can follow up with a compliment. “Hi, I’m ____________, what shall I call you? You know, you have the loveliest smile and it brightens my day every time I see it.”
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    Find commonalities. No matter who you talk to, if you talk long enough, you’ll find that you have at least one thing in common, be it where you’re from, or favorite food, or even a song you both like. And we like shared experiences and to feel a kinship with others. So, ask him questions and figure out what it is that you two have in common.[13]
    • After you’ve introduced yourself, and perhaps after a compliment or question, you might say something like, “That book that you’re reading, is that for a class? Oh, it is? What school do you go to? Hey, me too!”
    • This process of discovery is a great opportunity for you to learn more about this guy, and for him to learn about you.
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    Suggest getting together. You’ve made eye contact, you’ve approached him, you’ve introduced yourself, you’ve talked a little, and while you might not ask him out on a date right away, you can suggest informally getting together sometime. This shows him that you’ve enjoyed his company, would like to see him again, and that you’re warm and welcoming.
    • You’re extremely shy and this might be a terrifying idea. Remember, the suggestion is informal, no-risk, and non-committal.
    • You might say, “it’s been great talking with you _________. Perhaps I can buy you a cup of coffee the next time we’re both here.”
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    Keep talking to strangers. You approached your guy and started up a conversation. Bravo! That took a lot of courage. Keep up the good work and keep talking with others. Continued practice will help ensure that you don’t lose the skills you’ve gained, and also help ease your nerves the second time you talk to your guy.[14]


  • Don’t forget that practice makes perfect.
  • Remember that he’s human too and possibly just as shy as you are.
  • Cut yourself some slack and don’t overthink every single thing you say and do when you’re around him.
  • Be genuine when you smile.

Article Info

Categories: Overcoming Shyness & Insecurities