iPod 160GB freezes when i plug it in if a song is paused

Ok so here is the scenario: I had been listening to a song yesterday on the train home. Today i went to sync my ipod and when i plugged it in it immediately froze. It froze while a song was on the screen, it was paused and had been since yesterday.

This happens every time and the only way to do it is to reboot the ipod first (I usually forget to do this and it freezes and then i have to reboot it)

anyone know why this is happening. This has happened on every ipod classic ive owned with every (windows) pc that ive owned. My ipod firmware is fully updated blah blah blah.