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One thing I’ve learned is that starting a conversation with someone out of nowhere isn’t the best way to have a good conversation, especially if you’re already a socially awkward person. Instead you want to put yourself in situations with someone where a conversation naturally arises. For example, playing a board game that encourages people to discuss with each other or communicate. Or working on solving some problem together. That kind of thing makes it much more natural, and it also builds up your social skills so you understand how to make the more direct conversations actually work.