How To Conquer A Shy Guy In 1 Month: 20 Proven Strategies

Flirting with shy guys can be challenging, especially if you are outgoing and prefer fast, frank, and open flirting. As you already realized, the usual strategies do not work with this category of men. In this article, we will explain how to conquer a shy boy.

Here are 20 proven strategies on how to pick up a shy guy:

1. Approach him accidentally

Make sure there is a neutral “pretext” in between. Instead of directly approaching him to say hello or chat, approach under the pretext of asking for some information. The important thing is that in the first interaction he is clear about how he has to respond.

If you approach and simply say “hello” to him, due to his shyness he will not know what to answer you because his nervousness will prevent him from understanding what you expect of him.

But if you go over to ask him where the French room is, for example, you give him the opportunity to give you a concrete answer and to feel that he has some control of the situation.

After they answer, give them a brief smile, introduce yourself (if they haven’t already shown up), thank them, and leave. This will make it clear to her that you had a successful interaction with a girl, even if it was brief, and it will give her more confidence the next time you get close.

How do you know if a shy guy likes you?

You can’t just go and ask him directly if he likes you since with a shy boy this question is equivalent to burying him alive. You should use other methods a little more subtle, such as observing the way he looks at you, comparing his treatment with you and with other girls, among others.

2. Add him to social networks and find out what his likes and interests are

Shy guys usually have solitary hobbies, so they aren’t as obvious as a very outgoing guy who never misses an opportunity to say he likes sports or video games.

To know the interests of someone introverted, you have two options: observe very carefully or ask them directly. The best thing is that you opt for the first and, when you are sure that you have some common taste, use it as a topic of conversation.

If no matter how hard you try, you can’t figure out what catches his attention, ask him, but very tactfully. Many shy kids find their hobbies uninteresting (although they actually are) and are somewhat embarrassed to talk about them.

3. Don’t go straight into flirting

As tempting as it may seem, don’t flirt with her right away. What for any other man is a very clear and stimulating sign of dating, for a shy boy it can be a real headache.

This is because you will not be sure that it is a sign of flirting. You will simply detect that it is an unforeseen situation, you will get nervous and you will crash without knowing what to do.

Most likely, if you rush things, he will prefer to get out of that uncomfortable situation as soon as possible and will leave without giving further explanations. This will make things more difficult for both of you the next time you interact.

This is probably the most important clue to how to flirt with a shy guy: don’t make him notice that you’re flirting just yet. Simplify things to the maximum.

4. Look for indirect ways to be close to him

Try to stay as close to their radar as possible. They don’t necessarily have to be talking all the time, but it is recommended that he get used to your closeness.

Find a way to sit close to him in class, at work, or on breaks. Get closer to his group of friends. Add it to social networks. All this without pressuring him to have a conversation with you every time you are around. Just stick around.

5. Have a comfortable talk with him

Little by little, extend the time and topics of conversation with him until it is natural for both of you to talk every day. But for this to work, you need to keep the conversation on topics that he gets on easily with.

Avoid awkward silences and take the initiative by talking about yourself or asking simple questions, preferably that can be answered with a “yes” or a “no.”

Then you can go deeper with more open questions, but slowly. Don’t jump right in and ask him what he thinks of love or how many girlfriends he has had. It is about not putting him in front of situations in which he feels that he can make mistakes.

He will gain confidence, will realize that he has nothing to fear, and will be able to have a coherent conversation with you, without either of you running away.

6. Spend as much time with him as possible

Do not miss the opportunity to team up with him, sit next to him, or just come over to talk. If they are already growing in confidence, you can invite them very casually to go out to do some shopping they need or simply to walk together to the bus.

This shouldn’t be a problem, since shy guys are usually loners and it’s not like you have to “chase” flies in order to spend time alone with him.

7. Help him feel better about himself

Shyness often stems from a lack of self-esteem and that lack of self-esteem is also responsible for the introverted boy you like simply not realizing it or not believing it.

In order for her to realize that you are serious and to be able to respond to the flirtation without fear, begin little by little to compliment her and flatter her qualities. You must make it clear that for you he is someone who has many qualities and virtues. Someone who is attractive.

Remember that knowing how to win over a shy guy doesn’t happen overnight. So don’t rush. Take your time and subtly scale your compliments so you don’t make him uncomfortable.

9. Send him signs that you like him

Since he is convinced that you see him as someone who is very worthwhile, it is time, now, to send him signals that you not only see him as a friend but that you want something more.

It is very, very important that you do not rush through this step if he does not feel completely comfortable and relaxed with you, because if you go ahead, you will most likely only cause a panic attack.

Find a quiet environment where the two of you are alone. Try not to tell him that you like him or have romantic gestures with him in crowded or noisy places. Intimacy is very important and valuable to shy boys.

Give him hints of how well it would go together, have cute details with him, look him straight in the eye, and so on. Don’t jump in for a passionate kiss yet. Be patient. You’re doing well!

10. Ask him for help

Men adore the feeling of being the hero or savior of a girl in distress. Take advantage of this weakness and ask for help frequently: to transport something that is heavy for you, to reach something that is very high, or even to accompany you to a place to look for something. Obviously, he will not dare to refuse and thus you will have a greater opportunity to be intimate with him.

In this sense, asking for help is a great way to hook up with a guy, regardless of whether or not he’s shy. We all like that they raise our self-esteem a little and that they consider us worthy of help makes us feel more important and capable.

Surely your shy boy has ideal skills and aptitudes to help you solve certain problems or learn new things. Why don’t you ask him to help you with his culinary skills to prepare a dessert or with his technological knowledge to choose a new phone?

Of course, do not try to pass for a fool just because you are a woman. Whenever she helps you with something, be interested in learning so you can figure it out on your own the next time. So he will be delighted with your attitude.

11. Let him know that what he does is awesome

One of the main fears of a shy boy is losing control of the situation and that everything ends in a complete disaster.

That is why you must “let him see” that he is in control of the situation, that he controls the games, the flirting. Make him feel good about himself.

By this point, you have already made them friends and their confidence grows every day, so from time to time, you can ask them for a couple of suggestions or opinions about an activity that you are about to do.

12. Be interesting and dress more attractive

The fact that you are applying a couple of different strategies to conquer a shy boy does not imply that you will stop being who you are or will pretend something completely opposite to you.

You must remain as you are. There is nothing that makes a man fall in love more than a real girl. So show him, when you get the chance, how funny and smart you are.

Don’t be afraid to show your interests or if you disagree on an issue. These kinds of things are what spice up the relationship.

13. Take your time and don’t rush it

The first thing you need to understand is that this is a process of conquest that takes more time than it would take you to flirt with an outgoing guy. So the rush is not your friend.

If you rush the process, chances are you will scare him away. It is very important that before taking a step further, he feels completely comfortable and without pressure.

Shy guys can become completely blocked when they detect expectations of romance, not because they do not want to or because the girl does not attract them, simply because they do not know well how to interact.

Focus on the target

Your goal is that he does not feel nervous when he is with you and only until that moment can you go on throwing up flirting tracks.

It is completely understandable that on more than one occasion you feel that you are not moving forward with your boy or that your relationship has stalled. However, you should take into account that with a shy boy things will go a little slower than normal. You must be understanding and try to move at your own pace.

If you pressure him into getting into a relationship, making out, or just taking the next step, he will have no choice but to opt-out. Remember that no man likes to feel harassed.

14. Use social media a lot at first to talk to him

A boy can be extremely shy when it comes to speaking in person; however, it is usually more open and daring if the communication medium is a screen or a telephone. This gives you a sense of “security” and it is easier for you to interact through this medium.

Make sure that many of your conversations are by a digital medium of your choice and by text, if possible. Here you can be a bit sassy and wait for their reaction.

15. Pretend to be a shy girl

The first step is to create an element of compatibility between the two and the best is to show him that you share his shyness.

At this point, you should keep in mind that you will only be “a little shy” and avoid matching positions with him, since if both turn out to be too shy, who will take the next step?

Being a little shy will give you a special charm: you can smile at him and lower your gaze, look at him for a few seconds occasionally, obviously trying to make him notice and thus appear as shy as he is.

With a shy boy, you should be as patient as possible and avoid – by all means – harassing him or forcing your relationship to move faster.

If you suddenly start to flirt with him in a very aggressive way, his only reaction will be to run away, because he will feel like a stalked prey, and no man – no matter how shy he may be – likes to feel this way.

16. Say something nice

There is no man who can resist a compliment from the heart. Men love knowing that they are admired by their future girls and growing their ego is easier than it seems.

You can praise a man for his strength, his charisma, his intelligence, his professionalism, his character, or even his financial position. The most important thing is that, no matter what compliment you give, it is from the heart.

You can’t walk up to a guy and tell him he has dream abs if he looks like a washing machine. You must make him perceive sincerity in each of your words.

Many of the shy guys have low self-esteem (although this is not a common denominator), so congratulate him on any of his achievements whenever you can and make him feel better about himself.

17. Have light conversations

Being a shy boy, the most normal thing is that it takes a bit of work to start a chat or talk about himself. When you are with him, try to keep the conversations very casual.

You can address topics that don’t force him to talk about very personal things. Chat about trivial topics and, to gain more confidence on their part, you should set the example yourself and trust them with some secrets.

A tip that works wonders with shy kids to get them to talk is that your questions are open-ended; that is, they cannot be answered with a simple “yes” or “no”, but have to add a little more information. It is not the same to ask: did you like today’s class? what do you think of today’s class?

18. Little by little increase physical contact

Now yes: lose a little fear of physical contact so that he feels more comfortable every day with your closeness. Brush their hand as they walk. Kiss him closer and closer to the corner of his lips when you say goodbye. Take advantage of any excuse to hug him.

Take a good look at how he responds and his body language. If you do not notice that it is subtly or overtly moving away when you approach, then it is not bothering him. But if you notice that he is uncomfortable, slow down.

This works wonders as you start a stronger connection with your guy.

You must make sure that this physical contact is well received by him. You can try a pat on the shoulder and observe their reaction; If he seems to get uncomfortable with this, then you should avoid it and wait for his confidence to grow.

On the other hand, if it does not seem to affect him, you can do it from time to time, but without going too far. Touch only their arms or back without looking abusive. You can’t reach out and pinch pomp and pretend nothing happened.

You must respect his space and be careful since with a shy boy things are a little different.

19. Ask him out

Maybe the strategy of getting his friends to goad him out on a date didn’t work, so you can ask him out yourself. Remember that we are in the XXI century and the conquest is a matter of 2 and not only of men.

When you ask him out, make sure it’s a space where only he hears your proposal. Take advantage of the occasion, if by “accident” they are in a private place.

Mention that you need to go to the mall for something and that you would love for him to join you or something like that. This will not seem like a date and it will be much easier for him to accept and, of course, they can go for a coffee or an ice cream.

Avoid inviting him to places where the very idea sounds too compromising or where he may feel uncomfortable, such as a romantic dinner at a restaurant or a breakfast at your parents’ house. Make your first date seem as relaxed as possible.

20. Prepare a super romantic outing

For this to work, you should already be at the point where you can hug him or hold his hand without him having a problem with it. In fact, perhaps he is already encouraging himself to have some initiative with you and to test ground.

In order for things to settle down, organize a romantic outing somewhere that you both like and make you feel at ease; without many distractions and with an environment suitable for long and intimate conversations.

You have two options. You can confess how much you like him and see how he reacts, or go straight to steal a kiss from him. Depending on how things have evolved during your conquest process, you will decide which is the best option.

Knowing how to propose to a boy is not easy … that’s why most girls opt for the latter.