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Re:Ask HN: How to learn to be good at conversations with any... by retrac on Friday April 28, 2023 @12:40PM (#35743734)
Just something to consider: are you sure it's entirely you? And that you actually want to small-talk? I'm socially fluent and, at least when in the mood, can chat and bullshit about most things at length. But I don't like to. I'm socially awkward on the inside. I'm socially avoidant. And if you started chatting me up at work after about 30 seconds of pleasantries, unless I really like you, I'm trying to figure out the escape hatch to the conversation.

Anyway. Let the other person pick the conversation direction. Ask follow up questions, clarifications. Even try to guess what happened (when you know it's wrong) ahead of time so your misconceptions can be deconstructed by them. That often starts a further conversation. Let their mind wander, not yours, when you're looking for something to talk about. (You have lots of things you'd like to talk about but presumably you have no idea if they find it interesting. By letting them take the lead, you at least know if they wanted to bring it up!)

Maybe try loosening up if you tend to hold back. E.g. a little more off the beaten track, maybe something strange or weird (but hopefully not disturbing or alarming) happen to you recently? Tell a story about it.

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