Ipod won't allow me to check all songs for syncing.

Hello. My Ipod Shuffle won't plaiy all of the songs that it used to play, so I opened my library in Itunes. Some songs were unchecked, and these were the ones that are not playing. I tried to check them, but am unable to. The songs will play if I double click on them, however. I checked my preferences and I do not have the box checked that says "Sync only checked songs". Any ideas? Thanks!

The checking and unchecking of songs is done in iTunes, not on the shuffle.  And that may affect what is loaded in the shuffle during automatic syncing.  So first check what is actually loaded on the shuffle.
If the iTunes sidebar (along left side of window) is not visible, from the iTunes menu bar, under View, select Show Sidebar.
In the sidebar, find your shuffle under DEVICES.  Click the small trianle to the left of the shuffle name to drop down its content list (indented below the shuffle).  Click on Music there.  The list of songs currently on the shuffle is shown to the right.  Are the songs that do not play on that list, or not on that list?

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