Last Played is not correctly updating in Itunes

I have created a playlist that chooses songs that I have not played in the last 60 days and use this playlist to update my 1GB shuffle. Problem is that when I play the song on the Shuffle, and then re-sync, the Last Played date does not always update, even when I know I have completely played the song. The last played date is not properly displayed when viewing the Shuffle through Itunes either. For example, if I listen to 10 songs on a plane flight, maybe 2 will show up as having been played.
I am 1 day over chat support... bummer.

By the way here is the link to Itunes store in case it helps
http://itunes.apple.com/WebObjects/MZStore.woa/wa/viewPodcast?id=207881972

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