How do you know if a stranger (probably a shy or introverted one) likes you and when can he finally approach you?

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What I would do in this situation is find some reason, any reason to talk to him. You can literally just look out the window and comment on the weather, then look to him for a response. Or you can ask a question about current events and ask one person that’s not him for their opinion, then ask him.

Once you break the ice, it’s easy to keep talking.