It means (as far as my interpretation goes) getting on friendly terms (not to be confused with becoming friends) and see if they show signs of liking you back.
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No, see that's where you give up. If you're not getting signals from them then you leave it at that.
I don't see how simply stating you like someone will make you any more attractive. Hence, I don't agree with the just shoot your shot approuch among other reasons. If you ask me, I would take that as a sign they're not interested.