2 ipods with 1 iTunes - question

I have the old school ipod with 20 GB and then got the Nano last year which has 8 GB. Today I got a pop up message telling me something like I am close to exceeding the capacity for my Nano. As a result I unchecked some songs to make room for the new.
So when I went to update the new songs on my 20 GB I noticed that the songs I unchecked for the Nano remained unchecked. Why would it do that? I even shut down and restarted iTunes. My 20 GB can obviously hold the current songs plus the new, so there's no need to make room. Why would it do that? Can someone help me get back the unchecked songs on to the 20 GB? Thank you!

Thanks. I think Method 2 (copied below) is suitable for me, however, does it mean I have to create a playlist of my entire collection minus a few songs here and there for the Nano? For example, the default library will be for the 20 GB which is 1,900 songs. Do I have to create a playlist of 1,850 songs for the Nano (or whichever amount it will hold)? Thanks.
Method Two
You may use multiple iPods on a computer without the need to create multiple user accounts. To do this, you can set iTunes to update each iPod with only certain playlists. This method allows you to put all your music on, say, your iPod and keep your iPod shuffle updated with only your workout music. Here's how to do this with iTunes 7:
Create a new iTunes playlist for each iPod that contains all the music that you want to send to that particular iPod. Learn more about how to create playlists here.
Learn how to Sync your iPod, read the iPod Tutorial Steps section.

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