How to Talk to a Guy if You Are Extremely Shy

Co-authored by Eddy Baller and Hannah Madden

Last Updated: May 9, 2025 References

If you spot a cute guy at school or while you’re out and about, it might feel a little nerve wracking to approach him. You’re not alone—tons of people feel like that when they want to meet someone new! Thankfully, there are a few tips and tricks you can use to boost your confidence and figure out something to say to a cute guy.

1

Prepare a few conversation starters ahead of time.

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When you’re nervous, your mind might go blank. Spend a few minutes thinking about what you could say to the guy you like so you have some options. You don’t have to write a whole script, but jotting down notes about what to say might be helpful. Try things like:^{[1]
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- Asking about his weekend
- Seeing if he’s done the homework
- Talking about the class you’re in together
- Giving him a compliment

2

Act confident, even if you aren’t.

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Faking it until you make it really works! As you think about talking to the guy you like, picture the conversation flowing smoothly and asking questions confidently. Try not to overthink your conversation, and remember that it’s okay to be a little awkward when you first meet someone.^{[2]
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- Uncross your arms and stand up straight to look confident.

3

Make eye contact and smile at him.

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Your body language can let him know you’re interested. Glance in the guy’s direction and give him a small smile when your eyes meet. Turn your body towards him so he can tell you’d like to chat.^{[3]
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- If he sees you smiling at him, he might even come over and talk to you!
- Reader Poll: We asked 237 wikiHow readers and 84% of them agreed that smiling helps to boost your mood. [Take Poll] So, smiling may also make you feel more relaxed and ready to talk to your crush!

4

Take a deep breath to calm down.

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If you’re feeling nervous, stop for just a second to prepare yourself. Take a deep breath in and let it out slowly before you head over to chat with a guy. Taking a moment for yourself can help steady your voice and boost your self-esteem.^{[4]
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- The hardest part about talking to someone new is just doing it!

5

Introduce yourself to start a conversation.

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This is the easiest way to approach a guy, even if you’re shy. Simply walk on over and tell him your name, then ask for his. If you two already know each other (but not super well), you can remind him of your name instead. Say something like:^{[5]
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- “Hey, I’m Johnathan. Nice to meet you.”
- “Hey, I’m Emily. I think we have English class together.”
- “What’s up, my name’s Stephanie. What’s yours?”

6

Open the conversation with an observation.

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Comment on something around you to keep it casual. Take note of your surroundings and pick out something to talk about: is the new coffee shop you’re in serving delicious pastries? Does the library have a new copy of the novel you love? Say something like:^{[6]
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- “Wow, these bagels are so good. Have you tried them yet?”
- “Man, I didn’t know this book was out yet! Have you read it?”

7

Compliment him to let him know you’re interested.

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Leading with a compliment is a great way to keep his interest. Walk up and tell him that you like his jacket, shoes, or backpack. He’ll probably be grateful that you said something, and the conversation can flow from there. Say something like:^{[7]
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- “Whoa, cool pin. Where’d you get it?”
- “I like your shoes a lot. Are they new?”
- “Cool phone case, I love that color.”

8

Ask him open-ended questions.

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Open-ended questions take more time and effort to answer. Try to pick questions that don’t have a “yes” or “no” answer so he can expand on what he’s saying and talk for a few minutes. He might even ask you some questions, too! Try questions like:^{[8]
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- “What’s your favorite thing to do around here?”
- “Have you lived in the area for long?”
- “What’s your favorite class?”

9

Talk about your common interests.

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As you learn more about him, find things you can relate to. It’s super easy to connect with someone when you have stuff in common. Maybe you both go to the same school, or grew up in the same town, or just moved to the area. Say things like:^{[9]
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- “No way, I just moved here too! Where are you from?”
- “I absolutely love Game of Thrones. Were you mad about the ending, too?”
- “I have a dog too! Her name is Princess.”

10

Suggest studying together.

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If you go to the same school, this is an easy way to hang out. Ask him to study with you for the big test or help you out on the homework problems. If he’s interested, he’ll probably jump at the chance to see you again.^{[10]
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- Studying together is also a low-key way to get to know him more. Since it’s not a typical date, there’s no pressure on either of you.

11

Exchange digits to keep talking.

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If you like this guy, you probably want to continue the conversation. As it wraps up, offer to give him your number so you guys can keep in touch. It’s a low-pressure way to let him know you’re interested, and you can text him later. Say something like:^{[11]
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- “I’ve gotta go to class, but I’d love to talk later. Can I give you my number?”
- “That hike you were talking about sounds really fun. Wanna text me the details?”

12

Practice approaching others.

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Chat with people in line at the grocery store, your classmates at school, or people you’re sitting next to on the bus. The more you practice your skill of talking to others, the easier it will be to approach the guy you like!^{[12]
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EXPERT TIP

Eddy Baller
Dating Coach
Eddy Baller is a men’s dating coach and founder of Conquer and Win, a Vancouver-based service that helps men break free from loneliness and meet the women they truly want. Since 2011, he has coached men to overcome approach anxiety, spark real attraction, and build meaningful relationships—without relying on dating apps, gimmicks, or luck. Through both online sessions and in-person coaching, Eddy gives live feedback as clients meet women in everyday places, making confidence feel natural and conversations effortless. His mission is simple: to help men get into meaningful, long-term relationships.

Eddy Baller
Dating Coach

Our Expert Agrees: To get more confident, practice starting conversations with everyone you meet. That can be anything from talking to the barista at the coffee shop to the person in the checkout line when you're getting groceries. Building those general social skills will make you much more comfortable when you're talking to someone you'd like to date.

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Question

How do I tell a shy guy I like him?

Eddy Baller
Dating Coach
Eddy Baller is a men’s dating coach and founder of Conquer and Win, a Vancouver-based service that helps men break free from loneliness and meet the women they truly want. Since 2011, he has coached men to overcome approach anxiety, spark real attraction, and build meaningful relationships—without relying on dating apps, gimmicks, or luck. Through both online sessions and in-person coaching, Eddy gives live feedback as clients meet women in everyday places, making confidence feel natural and conversations effortless. His mission is simple: to help men get into meaningful, long-term relationships.

Eddy Baller

Dating Coach

Expert Answer

Try to acknowledge the unusualness of the situation. If you're approaching somebody directly and telling them that you like them, and they're shy, acknowledge the fact that you might have surprised them. Explain that startling them wasn't your intention, but that you had to take a chance because you were really inspired by that person.

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Question

How do you make a shy guy feel comfortable?

Eddy Baller
Dating Coach
Eddy Baller is a men’s dating coach and founder of Conquer and Win, a Vancouver-based service that helps men break free from loneliness and meet the women they truly want. Since 2011, he has coached men to overcome approach anxiety, spark real attraction, and build meaningful relationships—without relying on dating apps, gimmicks, or luck. Through both online sessions and in-person coaching, Eddy gives live feedback as clients meet women in everyday places, making confidence feel natural and conversations effortless. His mission is simple: to help men get into meaningful, long-term relationships.

Eddy Baller

Dating Coach

Expert Answer

Practice empathy by showing that you aren't oblivious to social signs and the fact that they're uncomfortable. Also, show them that you're not somebody who gets off going over their head and bulldozing into their space.

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Question

How do you talk to a super shy guy?

Eddy Baller
Dating Coach
Eddy Baller is a men’s dating coach and founder of Conquer and Win, a Vancouver-based service that helps men break free from loneliness and meet the women they truly want. Since 2011, he has coached men to overcome approach anxiety, spark real attraction, and build meaningful relationships—without relying on dating apps, gimmicks, or luck. Through both online sessions and in-person coaching, Eddy gives live feedback as clients meet women in everyday places, making confidence feel natural and conversations effortless. His mission is simple: to help men get into meaningful, long-term relationships.

Eddy Baller

Dating Coach

Expert Answer

When you approach a shy person, usually the topic of space becomes even more important. If you approach somebody who's really shy and realize quickly that they're really uncomfortable, take an extra step back to give them even more space.

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