Between the twitch friends I have made and the few communities I have dabbled in I have gotten a lot better myself about approaching others but it is still an occasional struggle in completely new places at least.
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Hi is always a good place to start imo and finding some small talk that lets you lead into asking about someone else's interests. That way you can try to find some common ground. Furality might have a macro meet up or some Tech furs meetups this year that can help you find some people.
sometimes you kind have to just force yourself to get into a circle of people and find a good moment to chime in. For me thats been the most terrifying part between the deuzear meet up I remember last year, and at Sylva meeting with the tech/IT furs and aviation furs was just getting into a convo
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