Using new shuffle with exsisting iTunes for my iPod

I tried taking some songs from my iTunes that I use for my iPod. Well on iTunes the songs are there but it will not let me eject my shuffle and the songs don’t play on my shuffle.

How are you 'taking' songs from your iTunes? And is it yours as opposed to someone else's?
Which "it" is it that doesn't let you eject your Shuffle? If you mean iTunes, how is it preventing it?
Finally, what led you to think that they got transfered to your Shuffle in the first place?

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