Since I've gotten my iPod shuffle, the fact that it updates the play count but not the last played date during updating has been bothering me. Since many of my playlists rely on this property of a song, this is very annoying. So I wrote a little AppleScript (zip file 8KB download) that reads in the iPod shuffle's playlist before updating, and compares the playcount to the values after updating. For those songs where it changed, it adds "now" as played date.
The iPod shuffle has to be kept in the Sources list for the script to work, and its name must be unique (no other playlists of that name). Simply change the property my_iPod in the script to whatever your iPod is called, and run the script.
As always: Use at your own risk! I take no responsibility for loss of data or any other malfunction. Make a backup of you iTunes Library file before you start...
[robg adds: I haven't tested this one...]
Mac OS X Hints
http://hints.macworld.com/article.php?story=20050331123345536