I have a deep fondness for love songs that voice the many whirlwinds of emotion, to not just show the saccharine sweet aspects but the anxiety, the feelings of being overwhelmed by all of it, this maelstrom of everything.
“Winter sings to fall” is such a song if you like to read it this way. This could be a song about someone who is being loved but nearly unaware of the amount, the intensity of this love. It might even be the love of someone who puts too much on this loved one (“while a bitter winter watches”) and who seems to nearly wish it weren’t so or at least wants just as much love in return (“you owe me for how much I love you”) which sometimes is not granted.
And if “Winter sings to Fall” is the title, then maybe it’s about an older person being in love with a (somewhat) younger person? Or maybe it is very literal, well, as much as it can be if winter sings.
Therefore, it could also be a song about the change of seasons and how winter watches as autumn gracefully moves through the world. Krug’s mentioning “Spider Season” which is apparently the time between September and October when all the spiders look for warm places inside houses and scare all the people “on top of our chairs”. A song about how autumn is this beautiful grace, the leaves in love with the wind who takes them for a dance. How winter watches, yearning, bitter even, because where the leaves are dancing for fall, they only lie dead for winter.
Who knows. Maybe I am completely off. But isn’t it a nice song?