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Hello, friend. If you are running iTunes below version 11, I can help you. Open iTunes and plug in your iPod. On the left hand side there should be your iPod name, go to your iTunes playlist and drag the songs you want to your iPod. For all of the songs, go to your iPod music library, even if you don't have songs, and on the bottom there should be a blue-ish bar. There might be a box saying "Autofill from iTunes library" click that ONLY if you want ALL songs from your iTunes to your iPod. Or You may try this ipod transfer, it's
a nice iTunes alternative that can help you manage iPod files including delete,
upload, play, copy, etc. It's much easier to use than iTunes. http://www.ipod-transfer-copy.com/ipod-iphone-to-computer-transfer-cucusoft.html
You need to set your iPod to update manually, instead of syncing automatically when you plug it into the computer.
To do this, plug your iPod into your computer, and on the iPod info screen that pops up in iTunes when your iPod is connected, click "Manually Manage Files." You'll now have to click and drag your songs from your library to your iPod, but now you can also play songs on your computer directly from your iPod and delete songs from your library without deleting them from your iPod at the same time.