I just play it by ear and hope she gets the picture
He doesn’t have the courage yet to go and get her for himself, so he’s just letting it come naturally, even though deep down he knows she won’t like him back. Furthermore there’s some sensory wordplay: He’s playing it by ear (hearing) and hoping she gets the picture (sight), which says even more that it isn’t gonna work because it’s two different senses, as opposed to him saying two things referring to the same one of the five senses. On the opposite spectrum, he could be saying that the two different senses could be a good thing and could help his chances, as it’s the senses working together like it does in the human mind.
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