I'm quite a shy person, although conversely I find it very easy to talk to people, I just need them to be the one to make the first move to open the conversation, once they've done that I feel more confident because I have the okay to go signal. At times it can be like breaking the dam, where starting a conversation with me leads to a flow that you weren't expecting. I'm an incredibly curious person and the way that I learn best is by asking questions. I will ask as many as I can think of, in an attempt to cement my understanding. What I have come to realise as a result of this process, is that other people love to talk about themselves, because for almost everyone it is the one topic of conversation above all else that they can be certain they are an authority on, nobody will know you better than you know yourself, no matter how close they think they may be to us.
Getting people talking about themselves puts them in a position of confidence and opens them up in a way that is hard to achieve with any other topic of conversation - having said all of that, there is a technique to it. You can't jump right in with intimate questions, most people won't want to answer them if they barely know you, and most people won't answer questions that give away details they consider to be too close to their heart. In this regard you need to probe a little bit before you find something you can start with. Whenever people have tattoos or piercings I find those to be the easiest talking points to pursue because in most cases the fact they are visible tells you that they want those things to make a statement about who they are or how they feel and when you ask them about those things it often leads to a depth that ordinarily it can take a long time to reach with people in general.
Fashion and style are also elements that can be a great point of entry because people put thought into how they look and they want it to give a certain impression, reading their style and their attitude to fashion can give you a lot of insight into a person's mentality before you even start talking to them. The more you know before you start to talk, the easier it is to talk.
One technique that I used when I was younger was to find common ground with people as soon as I could, but with age this technique has left me with many experiences that didn't prove to be as informative or fruitful. It is much easier to talk to people about things you know nothing about than it is to talk to them about things you do. When you talk about a subject you know nothing about, there is a lot of scope for asking questions, and there is a lot of opportunity for the other person to explain things, and crucially they don't feel as self conscious when describing something they are knowledgeable about to people who are not so, because there is no element of verification and validation in play, you won't be correcting them or their mistakes when they describe things that you know nothing about. That's not to say you should take their word as gospel, just recognise that the act and the experience is more important that factual accuracy in that moment.
I used to see people who had interests that I knew little about, and that would lead me to studying those things in my own time in order to make myself more knowledgeable on the subject matter - the problem with doing this is that most people have a shallow depth of reasoning. That is to say, most people don't question things that deeply, they form surface level understandings of the things they are interested in, only a few actually dig down and get into the technicality of it. Most people who have interests in specific sports for example have never dug down into the statistics of that sport, they know nothing about the history of it, or the background that includes all the information you will find if you actually do research on it. Instead those people will have their own experience, their own observations, and their own ideas of what it is and what it means - in other words they have a personal history with that sport which is why they love it, not the academic history. Reading a book about it won't reveal that personal history they have, the only way to learn about it is to actually engage with them in conversation and let them tell you about it.
You can take something like a game of Chess and know that most people who know something of Chess will know how to play it. As for the technical aspects of the game, such as the rank value of pieces, the scoring system, the classical opening moves, as well as the mathematical analysis of the pieces, which squares they are attacking at any given time etc, none of this will factor in their thought process unless they have actually researched the game and take it seriously to the point where they compete.
There's a simple lesson to learn here, if you don't know about something, don't pretend you do. Instead ask questions and engage in their interest, it is much more endearing to have another person take an interest in your hobbies and interests than to have them tell you things that you either already knew, or goes much deeper than your understanding which can cause insecurity.
Getting to know people is as much a game as any other part of life. There are moves you can make, there are payoffs and there are penalties. Which proves the most successful in the end will come down to experience and practice. The only way to gain confidence and proficiency is to practice. That may sound like something odd in the context of social interaction, but if you have trouble talking to other people you should understand that for most people for whom social interaction comes easily, they developed those skills when they were much younger. For those of us who have difficulty with these acts, we experienced a disruption in our childhood and our adolescence when these skills would normally develop. We therefore have to develop them later in life and the only way we can do that is through the same process that children and teenagers normally learn these skills - trial and error. The more you do, the more you learn, the easier it becomes. I started off life as an extrovert, became an introvert, and over time I am slowly restoring my extroverted nature, it's taking a lot longer than I thought it would though.
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