How to Flirt with a Shy Guy – Top 7 Flirting Tips

woman asking how to flirt with a shy guy

How to Flirt with a shy Guy – Start flirting right away!

Flirting in general is a skill to be learned, but flirting with a shy guy raises the stakes once more. Shyness is a nice characteristic, but it does come with some challenges in the dating area.woman wondering how to flirt with a shy guy

Fear of approaching someone, and showing interest are difficult tasks for a shy guy, which is where your part comes into play.

Here are our best tips on how to reach perfection in flirting with a shy guy. Applying some of these strategies will certainly help you overcome some of the challenges of dating a shy guy.

Not sure how to flirt with a shy guy and you may even wonder how to get a boyfriend down the road, even if he is shy? Read on!

  1. Signal him your Interest

  2. Ask him out Yourself

  3. Ask him for Assistance

  4. Listen attentively

  5. How to Flirt with a shy Guy? Be gentle and patient!

  6. Compliment him

  7. Text him

1. Signal him your Interest

Non-aggressive signals are the key to flirting with a shy guy, such as talking to the person more than to others, regularly keeping eye contact, or “accidentally” touching his arm or shoulders.

He will get the message without you having to say it right away.

2. Ask him out Yourself

Now, if you think the attraction is mutual, then don’t hesitant to ask him out. Since he’s shy, he most likely won’t do the asking.

Instead, shy guys are usually rather nervous around women in general. And, if he does ask you, he will take his sweet time, by which point you might have lost patience.

So the best thing to do is to ask him out yourself. Do it in an easy-going way, without expecting anything back. Ask if he wants to go have dinner with you and see a movie. Done! Then he knows you want to get to know him better and immediately starts to feel more comfortable.

3. Ask him for Assistance

Wondering how to make a guy like you? Ask him for assistance! Even if you don’t need it, ask anyway.

Do you need to build an Ikea book-shelf for a friend, or need help with your computer (hoping he knows computers!)? Shy guys tend to be helpful, and this is one way of getting to be around him before making a first move, and to assess the situation a bit better.

Then, as a thank you, you can offer to take him out for dinner (date!), or invite him for drinks afterwards.  It’s the perfect excuse to plan a spontaneous date with him!

How to Flirt with a shy Guy?!

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4. Listen attentively

One characteristic that is usually appreciated by shy guys is the ability to listen. Moreover, one of the perks of dating a shy guy is that they tend to be good listeners and expect the same in return.

Listen to his stories and his answers to your questions closely, and try to remember details from it, which you can use again in a later conversation. Come up with some good follow-up questions when the chance arises. He’ll be impressed!

Recommended: How to tell if a Guy likes You?!

5. How to Flirt with a shy Guy? Be gentle and patient!

As hard as this is during the flirting process, be patient with him. One of the rules with shy men is that shy men need time and you need to give it to him, if you want to keep flirting.

Don’t throw yourself onto him in an aggressive way and expect too much, too soon. This will scare him away, rather than that he will become more interested in you. Be calm and gentle when you’re around him, and wait it out to see what happens.

If there’s a spark, then things will take its natural course. You can still ask him out on a date, but don’t be too needy or upfront on the first date. He might not be into that, and could prefer the type who takes things slower.

6. Compliment him

He might not be used to it, so it will be a pleasant surprise if you give him a genuine compliment. Make it something special and catch him by surprise. He will love it!

Maybe even find something about him that others don’t notice often, and compliment him on that? It will make it even more special, and shows you’re thoughtful and attentive. You can also use this tactic to integrate some intimacy. Tell him how great his hair looks and then stroke your hand through it, or touch it with your fingertips.

Either way, keep in mind that complimenting a man is usually one of the best ways how to make a guy fall in love with you. So it cannot be a wrong thing either, when figuring out how to flirt with a shy guy.

7. Text him

This might sound strange, but as a shy guy, he will probably be less comfortable with direct contact in the beginning. Welcome to the 21st century!

Luckily, emails, texts, or Facebook messages don’t require face to face interaction and to get the conversation, or rather flirting, started, just text him. Ask for his number, and break the ice by texting him something quirky.

There’s no harm in using emojis to express your feelings too! Go for it, and if he responds, there’s clear interest. The same approach applies to emails and all other types of digital communication.

Try out what makes him the most comfortable, and then work your way towards a first, face-to-face date. With this, the risk remains low if the flirting goes sour, and you can make it fun and playful in the meantime.

So where do you start?

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How to flirt with a shy Guy – Relationship Guide!

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