There might be problems with your playlist saving incorrectly or something. Send me an email with the gw.exe.log file, found in your GrooveWalrus installation directory (or somewhere else, try using system search), and I'll fix the problem. Or if you don't want to do that try renaming/removing the playlist.xspf from:
XP
C:\Documents and Settings\[username]\Program data\GrooveWalrus
Win 7
C:\Users\[username]\AppData\Roaming\GrooveWalrus

If that fails:
You can try renaming/removing the gravydb.sq3 from the same directory.
gardener@turnip-town.net