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“Five String Serenade” is a cover of an Arthur Lee song.
It’s a mournful song about a lover who has gone away. The relationship may have ended and she moved on, the girl may have died, or something else ended up separating them: it’s not clear, but the point is that they are not together now.
He says, “It could be raining there too,” so he doesn’t know where she is, as evidenced by the suppositional “could be” phrase. If he knew where she was, then he would know if it’s raining in her location. In addition, he drew on his easel while he was thinking of her, so he most likely drew a picture of her. That he must think about her and draw an image of her, as opposed to having her actually there with him, further hints that they are separated now.
A serenade connotes playing outdoors, and the song says that it is raining. That he would play in the rain for her, wherever she is, establishes how much he loves her and misses her.
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