Change Playlist song order

Question

How can I make the songs on a playlist play in numerical order in my iPod shuffle?  They are playing in alphabetical order by song title.

Answer 1

The 4th (and 3rd gen) shuffle can hold multiple playlists like the other "big" iPods.  If you are looking at the main music list for the shuffle in iTunes, that is not a "playlist" (it is the shuffle's music library).  That list cannot be re-ordered like a playlist, just as you cannot re-order songs in your main iTunes music library.
If you load the shuffle manually, buy dragging songs to the shuffle, this is what you need to do.  Select the shuffle in the iTunes sidebar, under DEVICES.  NOTE:  If the iTunes sidebar (along left side of window) is not visible, from the menu bar, under View, select Show Sidebar.
Click the small triangle to the left of the shuffle name in the sidebar, to show its content list (indented below the shuffle).  Playlists on the shuffle appear there, on the content list.  If there are no playlists shown there, with the shuffle's name selected, click the plus sign at the bottom of the sidebar to create a new playlist.  A playlist appears on the shuffle's content list, where you can name it.
When loading the shuffle by dragging songs to it, drag the songs to this playlist.  That adds the song to the shuffle and to that particular playlist.  Since this is a playlist, you can select it and re-order the songs as desired.  When you play the shuffle, use VoiceOver to select that playlist (instead of playing from the All Songs list).  The songs will play in playlist order, if the shuffle's power switch is on the play-in-order (middle) position.