Currently Being ModeratedApr 21, 2013 1:19 PM (in response to Perchetti)
It depends on the model. This document shows the four types
For now, I'll assume it is 3rd or 4th (current) gen. Please post back if it is 1st or 2nd gen.
The latest iTunes may hide the sidebar; if it is hidden, from the menu bar, under View, select Show Sidebar.
If you load the shuffle manually (drag and drop items on the shuffle in iTunes), select the shuffle in the sidebar under DEVICES. Click the toggle (the little triangle to the left of the iPod's name) to drop down the iPod's content list, indented under the shuffle. Click on Music there. Over to the right, a list of songs on the shuffle is shown, Select the song you want to delete and press Delete on the keyboard. Confirm action. You can do this with one song, a selection of songs, or the entire list (Select All from Edit in menu bar).
If you use automatic syncing, the shuffle is synced with content based on how you set up the shuffle's Music tab in iTunes. When you select the iPod in iTunes, there is a row of "tabs" (starting with Summary). Click on Music there. This Music tab is where you tell iTunes how to automatically sync the shuffle. For example, you can have a playlist in iTunes with songs you want on the shuffle. That playlist can be selected on the Music tab, and iTunes keeps that playlist in the iTunes library and on your shuffle in sync. To add songs to the shuffle, add them to the playlist. To remove songs, delete them from the playlist. The next time you connect the shuffle (or click the Sync button), it is updated with any changes since the previous sync.