Sync only checked songs isn't working

I recently bought a nano for my husband (I already have an iPod classic). Since our music is pretty similar, I decided to choose the "sync only checked songs" option.
I thought I followed the instructions appropriately. I plugged in the device and selected it. When the summary came up, under options, I selected "sync only checked songs and videos". Then it did the sync, but that's NOT what it did-- it synced EVERYTHING! Then when I exited iTunes and went back in, the option didn't "stick." Am I doing something wrong? Any help or suggestions would be greatly appreciated because it's driving me crazy

*I selected "sync only checked songs and videos". Then it did the sync, but that's NOT what it did-- it synced EVERYTHING ...... then when I exited iTunes and went back in, the option didn't "stick."*
Did you click "Apply" down in the right hand corner of the Summary screen before syncing the iPod and/or before exiting iTunes?

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