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iPod Nano

 
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Member Since: May 15, 2009
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Mac Specs: White MacBook. iLife '09. iWork '09. Mac OS X 10.6

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That's probably it, but there is a function to turn off that dialog box and go with whatever option you set. Make sure you are deleting them from the list that says "Music" and not one of your playlists.

Chris K.
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