And there's a great deal of luck of course.
It's a matter of staying open to people and keep the conversation going without trying too hard (and that's the zen of it all
)
I have had some success making a conscious decision to turn down my internal censor so that the default setting is that it's probably okay to go ahead and say it anyway, unless it clearly jumps out at me as inappropriate. This combined with letting a medium mistake merely remain a medium mistake. And if someone needs space, go ahead and give them space without the intermediate step of asking whether they should need space.
I think I'm more appealing when I'm open and the world is a more interesting place.
Then I try and stay open to appreciating someone else.