How to Talk to a Shy Person

Talking to shy people need you to take a few things into consideration and certain things that you should and shouldn't do. A shy person's confidence can easily be knocked and so care on your behalf will be needed when you are wanting to communicate with them more.

If you want to, it might be a good idea for you to read my previous post: 11 Common Worries Shy People Have so you can have more of an insight to how a shy persons mind works. 
Here are some steps that can help you when talking and interacting with a shy person.

1. Be Smiley and Friendly

A smiley and friendly person is a lot more inviting for a person to talk to than a grumpy and miserable one. Shy people aren't normally the most forthcoming people in the world and so for them to know that you are a smiley and friendly person to talk to will make it a lot easier for them, and more likely, for them to come and talk to you. 

2. Don't Bombard with Questions

Don't hit them with question after question. Whilst questions are good to ask as they convey your interest in the other person and the conversation, too many questions and it will quickly appear to them that it is more like an interrogation than a conversation, which could make them become nervous - even if that were not your intention.
Shy people are good listeners, reason being is that they enjoy to listen to you rather than speak because they are normally afraid to, so watch how many questions you fire their way.

3. Don't act Nervous

Try not to be nervous around them as this can create awkward silences and conversations between the both of you. If you are nervous around them, it's not likely that they're going to take the reigns and steer the conversation to where you would like it to be, so try to stay relaxed and confident around them. This isn't an excuse to be arrogant or overly confident around them either as most shy people won't find that an attractive personality trait. 

4. Don't get too Personal

It's good to ask questions and it is something that is fine to do but try not to get personal. Many shy people aren't confident (hence their shyness) and aren't comfortable with discussing things that are personal, so try and keep the conversation related to the general topic but don't go into too personal an approach.  
They may also feel that their personal life isn't up to the standard to where you would respect or accept it and may feel embarrassed of it. 

5. Be Patient

It may take a lot longer than a single conversation for them to become comfortable with opening up to you. Prompting and encouraging them to continue, whilst you may see it as being kind and friendly, will most likely make them more nervous and try to withdraw from the conversation, feeling as if they are being put on the spot. 
They may need time to respond to your comments and questions, and may need that time because they respond in a certain way.

6. Don't be Patronising

Just because they are shy and can't articulate theirself as well as maybe you can, it doesn't mean you should become patronising towards them for them to understand. They will not appreciate this.  

7. Don't talk to them as if they are Stupid

Very similar to point #6, don't talk to shy people as if they are stupid just because they don't say a lot. Shyness does not amount to unintelligence...in fact some of the brightest and sharpest individuals on the planet are shy people.

8. Don't Tease them

Shy people don't like to be reminded of their shyness, especially when it comes in the form of people teasing them and joking about it. It may seem like a harmless bit of banter to you but to many shy people this is quite a degrading experience and is something they will very much dislike. It will often make them more shy and make it so they do not want to talk to you anymore. 

9. Listen to them

Listen to what they have to say and don't interrupt them or talk over them. Give responses and feedback that is genuine and engage yourself so they know that you are interested in what they have to say. Don't discredit or shoot-down their ideas as this will knock their confidence. It will have taken courage on their behalf to open up to you and talk about their ideas, if you just put-down their comments and/or not really pay attention to them it will have a negative effect upon their self-esteem - which may be very little as it is. 

10. Don't Point out their Shyness

This is different to teasing them about their shyness but is something that can still have the same effect. Simply pointing out that they are a shy individual can make them question their behaviour around you to why you would perceive them this way, and is another thing that could push them to become even more shy.  

11. Talk to them about something you have in Common

If you manage to find that you have something in common with this person, for instance like a hobby or interest, then try to get them to talk about this. Shy people will feel more comfortable talking to you about an interest they have if they and even more so if they know that you also share the same interest. Sometimes shy people, once got going, can really give a good conversation and can chatter on for ages. 

12. Talk to them about Something more Stimulating 

Don't just drone on about small-talk such as the weather. Things such as this will only become tiresome quickly and doesn't really cause the both of you to engage fully. Try talking to them about something more stimulating that properly gets the both of you engaged in conversation and thought.

13. React Positively to your Interaction 

When you are leaving one-anothers company, smile and let them know that it was nice talking with them. If you feel like it you can tell them that they are welcome to talk to you any time and can come over when they see you. You may even feel up to asking them to do something. Also be aware that if you are with friends and they see you they may not come over to you as they would rather a one-to-one conversation and may feel intimidated by your friends. If you do see them with your friends they may not want you to call them over, so a simple wave of acknowledgement would suffice.