it's not that user friendly to be honest. and neither is iTunes. To understand the program, you must think as an Apple Fan-person. that's the only way. (hint - figure out if "update songs automatically") is checked or unchecked. To remove the songs from your ipod, I say "manually update songs" instead of automatic, then click the songs I want to remove on my ipod (NOT MY LIBRARY), highlight all the ones I want by using control and click - then Right-click, CLEAR - and DONE!

Woot