My iPod nano (1st gen.) doesn't communicate with my pre-installed iTunes

I've had my iPod nano for just over a year now. It worked fine, including with my computer and iTunes, until my hard disk blew last summer. Since then, I've had trouble getting my iPod to work. Now I'm able to load it up with the Dock, and I'm pretty sure it's working normally.
However, my problem is that iTunes, which I had already installed several months before I reconnected my iPod, as I had some free song vouchers which were going to expire, doesn't recognize my iPod. I'm pretty sure there's a way to connect an iPod up to iTunes when the latter had already been installed, but I don't know how. Also, I have a lot of music on my iPod which I no longer have anywhere else. MY question is:
How can I connect my iPod up to iTunes (which has already been on my pc for a while) without losing any of the music on it?
Dell Dimension 8200   Windows XP  

Make sure all the songs in i-tunes are checked off (small box to the left of each song in the songs list), and click sync, or apply.

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