The secret isn't witty jokes or memorizing reams of factoids and stories. Such superficiality is nice as sugar and spice, but not as the main meal.
The secret weapon in good conversation, especially if you're an introvert, is to ask questions. Try to make them open ended, not yes or no, and not right or wrong. Essay questions. Where are you from? What do you do?
Several months ago, there was an article here about a man who would ask the person he met what they did for a living and then, no matter they said, he would remark, "That sounds hard." This triggered a torrent of conversation and feelings of intimacy. That technique crosses over into artificial formula, and so I actually wouldn't recommend it. But it illustrates a point, that people are dying to be heard.
People aren't looking for a walking, talking encyclopedia. For one, the world is overrun with information, thanks to books and the internet. For another, it puts you on uneven footing. Now you are the teacher, and they are the student. People are repelled by condescension. They mainly are looking for people with whom they can be on equal footing.
There are also degrees of intimacy. The weather is a good opening remark with someone you just met, because it's not about either one of you. On the opposite end is something like, "How are you feeling after your recent divorce?" This is something you get the right to ask only after a very long time, perhaps years, of trust. Between those two is a spectrum.
1. Things about neither one of you, and uncontroversial: the weather, a movie, a sports game
2. Things about each of you, but not intimate: your job, what part of town you live in, what town you came from
3. More and more personal things about each of you: college major, family, children, how much you like your job
The first time you meet someone, you may not go very deep. But if you ask questions, be supportive of their answers as best you can, ask logical next questions that show you listened, and so on, then ironically you will be called "a great conversationalist."
The only thing I might add is that you can err too far on asking questions. If you're asking all the questions, and they're doing all the revealing, it may seem creepy. When they reveal something about themselves, then it may be a good time to reveal a corresponding amount about yourself. For example, if they tell you their job, then you tell them yours. Some people actually talk about themselves first, but as a way to let the other person feel safe to open up. For example, instead of asking what they think about the weather, you say, "Boy, it sure has been unseasonably cold." Then they will feel like agreeing or adding to it. "Yes, but at least I get to go skiing more." "Oh, you like skiing?" The best topics are ones that flow naturally from the last topic. That's another reason to listen closely.
So again, the point is not to entertain the other person but to at least start with the promise that you could one day be a trusted friend. That could take years, and for most people you meet it will never happen. But I would say that the same steps you take on the long road to a good friendship are the same steps you take one conversation at a time.
The secret weapon in good conversation, especially if you're an introvert, is to ask questions. Try to make them open ended, not yes or no, and not right or wrong. Essay questions. Where are you from? What do you do?
Several months ago, there was an article here about a man who would ask the person he met what they did for a living and then, no matter they said, he would remark, "That sounds hard." This triggered a torrent of conversation and feelings of intimacy. That technique crosses over into artificial formula, and so I actually wouldn't recommend it. But it illustrates a point, that people are dying to be heard.
People aren't looking for a walking, talking encyclopedia. For one, the world is overrun with information, thanks to books and the internet. For another, it puts you on uneven footing. Now you are the teacher, and they are the student. People are repelled by condescension. They mainly are looking for people with whom they can be on equal footing.
There are also degrees of intimacy. The weather is a good opening remark with someone you just met, because it's not about either one of you. On the opposite end is something like, "How are you feeling after your recent divorce?" This is something you get the right to ask only after a very long time, perhaps years, of trust. Between those two is a spectrum.
1. Things about neither one of you, and uncontroversial: the weather, a movie, a sports game
2. Things about each of you, but not intimate: your job, what part of town you live in, what town you came from
3. More and more personal things about each of you: college major, family, children, how much you like your job
The first time you meet someone, you may not go very deep. But if you ask questions, be supportive of their answers as best you can, ask logical next questions that show you listened, and so on, then ironically you will be called "a great conversationalist."
The only thing I might add is that you can err too far on asking questions. If you're asking all the questions, and they're doing all the revealing, it may seem creepy. When they reveal something about themselves, then it may be a good time to reveal a corresponding amount about yourself. For example, if they tell you their job, then you tell them yours. Some people actually talk about themselves first, but as a way to let the other person feel safe to open up. For example, instead of asking what they think about the weather, you say, "Boy, it sure has been unseasonably cold." Then they will feel like agreeing or adding to it. "Yes, but at least I get to go skiing more." "Oh, you like skiing?" The best topics are ones that flow naturally from the last topic. That's another reason to listen closely.
So again, the point is not to entertain the other person but to at least start with the promise that you could one day be a trusted friend. That could take years, and for most people you meet it will never happen. But I would say that the same steps you take on the long road to a good friendship are the same steps you take one conversation at a time.