If your iPod is set to update automatically you need to take care connecting to an empty iTunes. You can use a keyboard command to prevent your iPod auto-syncing with iTunes. While connecting the iPod to the computer on Windows with iTunes 7.3 or later installed hold down the Shift + Ctrl keys together. This will stop the iPod from auto-syncing with iTunes and the iPod will appear in the source list. Wait until you are sure the iPod has mounted, and that it will not auto sync and then you can let the keys go. This may take between 20 to 30 seconds depending on your computer:
iTunes - Keyboard Shortcuts for Windows
When your iPod appears in the iTunes source list change the update setting to manual, that way you can continue to use your iPod without the risk of accidentally erasing it. Also when using most of the utilities listed below your iPod needs to be enabled for disc use, changing to manual update will do this by default:
Managing content manually on iPod and iPhone
Once you are safely connected there are a few things you can do to restore your iTunes from the iPod. If you have any iTunes Music Store purchases the transfer of purchased content from the iPod to authorised computers was introduced with iTunes 7. You'll find details in this article:
Copying iTunes Store purchases from your iPod or iPhone to a computer
The transfer of content from sources such as songs imported from CD is designed by default to be one way from iTunes to iPod. However there are a number of third party utilities that you can use to retrieve the music files and playlists from your iPod. You'll find that they have varying degrees of functionality and some will transfer movies, videos, photos, podcasts and games as well. Have a look at the web pages and documentation, this is just a small selection of what's available, they are generally quite straightforward. You can read reviews and comparisons of some of them here:
Wired News - Rescue Your Stranded Tunes
Comparison of iPod managers
TuneJack Windows Only (iPhone and iPod Touch compatible)
iPod2PC Windows Only
iDump Windows Only
SharePod Windows Only
iPodRip Mac & Windows
YamiPod Mac and Windows
Music Rescue Mac & Windows
iPod Music Liberator Mac & Windows
Floola Mac & Windows
iGadget Mac & Windows (iPhone and iPod Touch compatible)
iRepo Mac & Windows (iPhone and iPod Touch compatible)
iPod Access Mac & Windows (iPhone and iPod Touch compatible)
TouchCopy Mac & Windows (iPhone and iPod Touch compatible)
There's also a manual method of copying songs from your iPod to a Mac or PC. The procedure is a bit involved and won't recover playlists but if you're interested it's available on page 2 at this link:
Copying Content from your iPod to your Computer - The Definitive Guide
Whichever of these retrieval methods you choose, keep your iPod in manual mode until you have reloaded your iTunes and you are happy with your playlists etc then it will be safe to return it auto-sync. I would also advise that you get yourself an external hard drive and back your stuff up, relying on an iPod as your sole backup is not a good idea and external drives are comparatively inexpensive these days, you can get loads of storage for a reasonable outlay.
