Crack jokes, banter, wear a smile, but don't be a clown.
Best way is to surround yourself by people who do the same. Do not feel discouraged when they "throw a knife" (take the piss) your way, as it's a test of your conversational and mental frame. Agree and amplify, and laughs will be had.
Then again, don't surround yourself with bullies. A true friend stabs from the front to test and grow your mental frame, while enemies stab from the back to undermine your frame.
Point is, have fun. Don't be a walking talking wikipedia page of logical facts.
This is sort of what I am. I think it started long ago maybe when I felt as if this is one way I can provide value: to give you facts.
I'm aware that this is a problem, in that by doing this I'm not really engaged in a back-and-forth conversation -- I've been aware of this for some time, it's just that it's hard to transition away from this. I don't know how to do this, because this is who I am now, and changing who I am, that’s a deep change to make, it is hard, and I don’t know how I can do this.
It might be useful to -- consider that your information is... not useful.
By this I mean that you should be interested in how people react to new information in general. In some cases, people take this information and act on it. In most cases, they don't. It's very hard to convince someone, especially a stranger, to do something differently just by providing them new information.
Don't take my word for it. You don't even need to look to others to find the truth to this. Just look to yourself.
How often do you tangibly change your actions based on new information? I'm sure you have some less than desirable habits, and I'm sure you have know enough information to know that these habits are not helpful. Yet, even with this information, have you changed these habits?
I am similar. I sometimes struggle to engage in conversation... I'd rather just walk away and do something interesting to me. And this is fine, you don't need to always engage in conversation. But when you do, it shouldn't be to just dump information on people. This isn't effective. Even with people who you have close, intimate relationships with... it's even hard to change these people. Even if you do have the right information, it needs to be delivered with patience. You can't expect them to change overnight. You can't even expect them to change at all. If you want to tell someone something, you must do it with compassion, and expect that if they are going to take this information from you, it will be on their own time.
You must gain confidence. Have confidence in yourself, and you will find others will do the difficult conversational parts for you. The quickest way to gain confidence is to learn to lift compound weights and to increase the weight over the years.
Beyond that, remember to relax and be yourself. In my experience, people aren’t judging you nearly as much as you think they are.
- How to Win Friends and Influence People by Dale Carnegie - Never Split the Difference: Negotiating As If Your Life Depended On It by Christopher Voss
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.