iTunes and Shuffle Difficulties

[AutumnSkyline]

So since the 7.3 update, my iTunes has been acting strange every time it would switch a song (I play my music directly from my iPod). It would pop up with:

That also sometimes pops up when I try to add a song

Clearly, Jimmy Jr. is attached:

What is the problem

EDIT:

I just caught a screen of it when it was switching to the next song: