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I reckon almost everyone has, but don't know that they have.
At somewhere just above 0.5% of people (in the USA and UK) identifying as trans, you'd only have to meet 200 people on average to meet someone who does.
That was bad wording on my part; meeting someone who is trans is fairly likely but knowing someone who is openly trans (and therefore discussing this with them and gaining a better understanding of it) I imagine is somewhat rarer. I've updated my post.
I think many people would be surprised how many trans people they've met without knowing.