There are two methods.
- From the Main Menu, go to Settings/Shuffle and press the centre button. The option will toggle between off/songs/albums. Set it so that is says Songs. Then navigate to the Playlist you want to play until the Playlist name is highlighted. Press the Pause/Play and one of the songs in that playlist will be chosen at random to play. The iPod will play the rest of that Playlist in Shuffle mode.
- Navigate and enter into the Playlist you want, choose the first song that you want to play and start it playing. While it is playing, press the centre button three times until the Off - Songs - Albums shuffle option appears. Use the scroll wheel to highlight Songs and press the centre button to select that mode.
When the iPod is in Shuffle mode, it will display the Shuffle icon in the top right of the Now Playing screen:
Thank you for your response. You have totally solved my problem. Definitely worth 10 points. May I also point out that when I tried this at first I did not think it had worked because I was looking at the track numbers rather than the song titles. I was expecting it to display the track numbers randomly rather than the song titles.
Ah! I see your confusion now!
The number in the Now Playing display (in the picture above, that's 2 of 31) means that it's playing the second song in the current sequence and the total number of songs in the sequence is 31. A "sequence" is either a Playlist, artist, genre or even a song in the total songs menu. In other words, whichever playlist or menu you are using, it has 31 songs, and you have already played one song from this list and this is the 2nd one in the sequence.
So as the player is currently in Shuffle mode, this could be song number 4, 16, or even number 31 in the Playlist, and that you have already played one song from this Playlist. So once the display shows 31 of 31, then you know that you heard all 31 songs and that you're about to be plunged into that awful world of "I can't hear any music!"
If you stop the current Playlist after three songs have played, and play a song from another Playlist, an album, or genre etc., and then return back to that original Playlist, the first song you play will show up as 1 of 31, because you have started the sequence again.
If the player is in normal (non-shuffle) mode, then if you go back into the same Playlist of 31 songs and start playing song 4, then the display will show 4 of 31. Once song four has finished, songs 5 - 31 will play. The last song to play will be 31 and show in the display as 31, but you will only have heard 27 songs.
I hope that's cleared up any confusion.