If I delete a song on my iTunes, why does my iPod ask me if I want to transfer it back?

I get a message during synch of my iPod (Classic) that says "there are purchases on your iPod that are not found in your iTunes library - do you want to transfer these?" This always makes me paranoid that maybe I have songs I want on my iPod that somehow aren't in my library, so I used to say "yes"....but then after a while, it seemed apparent that what was "missing" from my library are songs I have purposely deleted.  So then I was going through this endless loop of deleting, then transfering back, then deleting, then transfering back, then deleting......
So, my question is: if I delete a song or game or whatever in my iTunes library, shouldn't it then just remove it from the iPod?  As I mentioned above, I find it confusing/alarming when it starts asking me if I want to transfer stuff back from my iPod.  Not sure how to tell what it is that it wants to transfer back?  Is there any setting that would tell iTunes that when something is deleted in the library, go ahead and delete it from the iPod?
Thanks!

If there a way where I won't have to delete it?
I have these on my phone, ipad, home computer, and work computer.  If I listen to something, then I may have to delete 2 or 3 times on all these devices.
Thanks

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