iTunes won't sync songs

[mknabster]

I just finished creating a playlist in my music library, and i have been trying to transfer it to my iPod Touch 3rd gen running iOS6 and my iPad 2 running iOS 7.1.1. They're not plugged in at the same time, but when i try to do either of them individually, nothing happens. The songs show up in Music under each respective device, but they are opaque with a little dotted circle to the far left for each. Now if i try moving a song from a different playlist or the main music library itself, same thing. Now i chose the Trust this Computer prompt i was given when plugging the iPad 2 in, didn't get that with the iPod. What's going on with this, i have never had this issue in the past with previous versions of iTunes, why is it happening now? Any help would be appreciated because i spent 4 days building this playlist and i would like to be able to use it.