How to Flirt With a Shy Guy

Co-authored by Sarah Schewitz, PsyD

Last Updated: December 1, 2024

Interested in a shy guy? It can be trickier to like a shy guy because it’s harder to tell when he’s into you. However, there are ways to get him to open up and move him out of the friend zone.

Method 1

Method 1 of 3:

Talking to a Shy Guy

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1
Figure out what he likes. Start by figuring out what his interests are and then talk to him about them. Most people are comfortable talking about things they like to do.
- Maybe he likes a certain band or loves videogames or movies. Or maybe it’s a sport he’s interested in.
- Act genuinely interested in his interests (but if his interests truly bore you and you’re completely faking it, consider that he’s not the right guy for you.)
- Even better yet, figure out areas of common interest that you both like and start there so that your interest is genuine. Just be yourself.
2
Ask him questions. One of the best communication techniques to get a shy person to open up is to ask them questions rather than uttering statements.
- Make the questions casual, not nosy. Ask him about something he likes to do or is interested in, such as whether he saw the latest movie with his favorite actor.
- Asking questions draws shy people out of their shells by helping stimulate their side of the conversation. Use your intellect.
- Ask open-ended questions. These are questions that are phrased to elicit an explanatory, detailed response. Start the question with words like what, how, in what way, and why. Asking questions that start with words like “do” will provoke terse, single-word yes or no responses.
EXPERT TIP

Sarah Schewitz, PsyD
Licensed Psychologist
Sarah Schewitz, Psy.D. is a licensed clinical psychologist by the California Board of Psychology with over 10 years of experience. She received her Psy.D. from the Florida Institute of Technology in 2011. She is the founder of Couples Learn, an online psychology practice helping couples and individuals improve and change their patterns in love and relationships.

Sarah Schewitz, PsyD
Licensed Psychologist

Help your shy guy feel more confident. Love and relationship psychologist Dr. Sarah Schewitz says: "You can get to know someone who's shy the same way as anyone else. You just may need to ask more questions and lead the conversation more. Also, try not to interrupt them, so they'll feel confident when they're talking to you."

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3
Ask for his help. Maybe it’s just conversation that unnerves the shy guy and stands outside his comfort zone.
- He’s probably an observer who’s deep but has trouble expressing that to strangers or people he doesn’t know very well.
- Flirt with him by asking for his help with something. A lot of guys do feel comfortable with being the person who helps out. Consider it their inner knight coming to the surface.
- Whether it’s help with your car, a math equation, or a stuck locker room door, ask if he can help you out. Don’t ask him for help with emotional problems, though, at this point.
4
Compliment him. Everyone likes to be complimented. It’s human nature. A shy guy is going to be no different.^{[1]
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- So point out you like the color of his shirt. Or that you like his new jeans or his haircut or the way he thinks.
- Don’t just point out his physical appearance, point out an attribute about him that you like. Perhaps it’s his loyalty or how smart he is at a certain subject.
- Say his name a lot when talking to him, and give him a lighthearted but complimentary nickname. This will probably get him to laugh and open up.

Method 2

Method 2 of 3:

Using Non Verbal Communication with a Shy Guy

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1
Use positive body language. Some shy guys are observant and likely to pick up on the smallest signals of flirtation that others might miss.
- Play to this strength of his by using body language to flirt with him and communicate that you like him. People’s body language can convey interest or disinterest in another person. Lean forward and make eye contact with him.
- To communicate interest, keep your body language open. Smile when you see him. Smile a lot and big. Look him directly in the eyes when you first smile, and then quickly glance away, looking down while still smiling.
- When talking to him, keep your feet pointed toward him not away from him. Don’t crowd his space too much, but square your body toward his. Laugh at his jokes.
- Don’t cross your arms or your legs as this can be a sign of closing off and can signal a lack of interest to someone who’s paying close attention. Touch him lightly on his shoulder.
2
Repeat the clues. The shy guy might be insecure and he might not be sure you were really flirting with him the first or even the second time you do it.
- If you smiled at him in the hall, he might think you were just being nice until you do it the third time or more.
- The key here is to send him the signals more than once so he grows confidence in the fact that, yes, he’s actually getting them.
- If you pursue him too aggressively, he might back away, so do this subtly. The art of flirtatiousness is to remain a little mysterious while still accessible.
3
Flirt in writing first. It’s a sign a shy guy likes you if he communicates with you by text or email a lot, but doesn’t talk to you. His friends might tease him when you’re around because they know he likes you.
- That might just mean that he’s less comfortable with verbal communication. Reach him through pathways that are in his zone of comfort. Some shy guys are deep thinkers who may respect wordplay.^{[2]
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- In addition to texting and writing him, click like on his pictures on Facebook or add a breezy and positive comment to a post he’s made.
- Use emojis to flirt. Don’t be afraid to text him something first, just keep it light. Can you believe how hard that assignment was? Could be a good opening. Send him a friend request.
4
Hang around him. In order to , make sure you’re around him more often, just do it in a subtle manner.
- Sit a little closer to his table in the lunchroom, for example. If you know he walks his dog in the park every morning at a certain time, go jogging there.
- Put yourself in situations where you can easily strike up a conversation. Sit just beneath him at an athletic event or school dance, for example.
- If he’s older, show up at the coffee shop where he works on his computer in the mornings and sit at the table next to him.

Method 3

Method 3 of 3:

Making a Shy Guy Comfortable

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1
Approach him individually. If he’s a shy guy, then he’s probably uncomfortable in large groups of people, especially those he doesn’t know.
- That’s especially true of the girlfriends of the girl he might secretly like (you). You’ll have to get him to open up to you by flirting with him one-on-one.
- Shy guys are going to withdraw more if you always come around hanging with a pack of girlfriends. Separate from the herd!^{[3]
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- Approach him in a setting where your flirting won’t be on display: by his locker room, as he’s walking to his car, and so forth, not in the lunchroom where he’s also sitting with others. If he’s an older shy guy out of high school, the same applies.
2
Stay in his comfort zone. To , don’t make it too obvious. There’s no magic equation you need to know or master. Just be yourself.
- That means being friendly with him in a casual way, by approaching him and saying hi or striking up a conversation about an area of mutual interest.
- You could mention a particularly tough homework assignment or, if he’s older, a sports team’s loss or victory (if he’s interested in that).
- The goal here is to not act too obvious with your flirting. Flirting is really about showing interest in another person, and with a shy guy, you should start low key and friendly.
- Reader Poll: We asked 912 wikiHow readers how they would approach an introverted guy to show you’re interested, and 74% said they would get to know him as a friend first. [Take Poll]
3
Recognize whether he’s into you. All of this is well and good, but one of the most difficult parts of flirting with a shy guy is trying to figure out whether he’s interested in you.
- If he gets nervous around you, by stammering or blushing or the like, he’s probably interested in you.^{[4]
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  Research source} If he asks your friends about you, that’s a sign of interest.^{[5]
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- Pay attention to his body language back. Does he use open body language to indicate he’s receptive to the flirting? A shy guy might feel intimidated around you which may seem like sometimes he's uncomfortable, but the more you hang around him the more he'll feel relaxed around you, Don't make it hard for him too! A huge turn-off is to only talk to him about problems, or use him as a vent-doll, Let him talk too, Get to know him a bit, make him feel good around you, make him feel safe around you, make him feel excited to see you!
- If he teases you, jokes, or acts silly around you, he probably likes you. This is a way that shy guys cover their unease and embarrassment. He might be shy but that doesn’t necessarily mean he’s an introvert. Introverts are personality types who gain energy through being alone.
- If he goes silent around you, it’s not necessarily a sign of disinterest from a shy guy. The more he actually likes you, the more uneasy he will feel around you.
4
Be patient. Don’t give up on a shy guy too soon. It’s going to take a bit longer for him to pick up on and then acknowledge your cues.
- It may very well be worth it in the end though because the shy guy doesn’t flirt with everyone. Thus, when you get him to flirt with you back, you’ll know it means something.
- Don’t hesitate to be the person who initiates at first. You might even be the one who has to initiate the first date. Ask him somewhere casual at first, for coffee or to a movie. You might wait forever with a shy guy if you wait for him to make the first move.
- Guys are shy for different reasons. Maybe he’s been rejected before or it stems from a childhood experience. More likely it’s just genetics. He’s a quiet type. That’s who he is.
5
Accept his shyness. Dating a shy guy is not a bad thing. Many shy people are thoughtful, introspective people who are often deep thinkers.
- It’s a mistake to try to change anyone. Don’t expect that, by flirting with him or dating him, you can turn him into something he is not.
- Accept that this is his personality type and work from there. That doesn’t mean, though, that he won’t come out of his shell a bit as you get to know him better.
- It’s human nature to want things you have to chase a bit. The shy guy is appealing sometimes because he’s a bit mysterious and doesn’t give away everything to everyone. Thus, if you become his eventual confidante, you’ll feel very special.

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Tips

Make him laugh. If he knows you can let loose, it'll make him more comfortable around you and he'll feel like he can trust you.

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Laugh at his jokes if he tells you one.

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Be sweet as much as you can. Give him sweet compliments.

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Warnings

Don't be mean to his friends. He will get angry with you.

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Don't act really intimidating.

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Don't be too aggressive in your attempt to win him over.

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Don't flirt with other boys, as this will make him think you don't like him.

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