The 'last played' function doesn't update

When I play a song on iTunes it's information (number of plays, date and time of its last play, etc) update as they are supposed to. However this doesn't happen when I play a song on my iPod Touch (even though it used to). I don't have the cross-fade function turned on. I'm wondering if it has anything to do with a newer version of iTunes that I may have updated, although I cannot say which if in fact this is the case since this isn't an issue that I noticed straight away.
It's only a small problem I know, but I enjoy listening to playlists where the number of plays and how recently I've listened to songs (say within the past 4 days) are the important factors, and for the moment I cannot do so. So i would appreciate any help that anyone might be willing to give regarding this. Cheers