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Viliam_Bur comments on Open Thread, August 16-31, 2012 - Less Wrong
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Practice conversation and you will get better at it. That's it. More helpfully, if there is a random stranger near you, you can open them and talk for a bit about any random smalltalk bull you like. This will improve general conversation skills. If you live in a large anonymous city you don't need to care if people think that's weird because people will not be getting together to share these impressions. Advice I picked up from reading PUAshit; jump between topics without feeling the need to link them or segue at all. Advice that sounds good that I haven't tried out; record yourself in conversation to pick out flaws. Oh, and pause, don't um. Improv will help, and remember, keep calm and carry on.
Also, choose topics where inferential distance for a random person is small. This is what allows talking instead of explaining, and easy jumping between the topics. Avoid controversial topics, such as money, politics, religion.
A good topic is easy to understand, and does not divide people into opposing groups.
What topics aren't controversial and within a short inferential distance from most people? My intuition is that this is close to the definition of "boring".
Listen to actual conversation sometime, most of it is excruciatingly boring if you think about it in terms of information. But as other posters have pointed out, most conversation is about social bonding, not exchanging information.