I definitely have this problem with my library. It's f---ing enormous (78K songs) and I've only *really* listened to about 2/3 of it. But I kind of like it that way. My system basically works like this: I'll nick anything that even remotely piques my interest and put it in there. With some things, I listen to them right off--sometimes just once, sometimes they sink in enough to get on repeat for a while. But then there are lots of times when I'm not sure what I want to listen to and this is what the shuffle feature is for. I shuffle until I come upon something interesting and usually end up rediscovering something I've had for a while but never significantly paid attention to before.
That's why I'm loathe to get rid of things, even if I haven't really listened to them much or at all since I've had them--because I know myself and I'll probably come back around to them at some point, even if it takes me a couple years.
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Like carnivores to carnal pleasures, so were we to desperate measures...
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