ANSWERS: 3
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No, the songs need to be on your computer for them to stay. Not that it matters, just download the songs that he has from the net and you should be fine.
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Note that I'm not advocating music piracy. When you sync the iPod with iTunes for the first time, it will wipe the iPod clean and replace it with the library on your computer. You will have to copy the files off of your iPod using a program like Ephpod: http://www.ephpod.com/ to copy the music files off of the iPod, and then put them into your iTunes library and reimport them.
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The other answers are WRONG! You can do this as long as the iPod is NOT sync'd to your PC. If the iPod has never been plugged into your PC then it is, by default, NOT sync'd. If it has been used on your PC then it could be sync'd and you need to remember/ask if it was sync'd or not, personally I keep mine UNSYNC'd as I have 60GB on my iPod and only 100GB on my comp.
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