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If on iTunes it will only allow music that you have purchased from iTunes. Anything else it sees are pirated. You can get over this by buying an iTunes Match subscription. This allows you to transfer any music it iCloud and iTunes, so when you synch, all your music is there. You can drag your music from Windows Media player to iTunes.
If you are using a Windows phone, just Google the problem as someone will have come across it before.
Rather than Synching, you may be able to drag individual tracks to the player. Synching does what it says, it make the one device the same as the other device, so if there are tracks on the player that are in Windows Media Player, it will remove them so both are the same. There may be a setting to NOT Delete what is on the player, just Update New Tracks.
If you try to sync with Dad's PC via iTunes you will lose your music. However take a look at XPlay 3 from mediafour.com; that will allow you to recover music from your iPod onto a PC.
If you need to do this on a Mac try Senuti.
Try it on another computer and if it happens its the ipod.
Or try restalling itunes with the lates version (7.7.1)
If that doesnt work try using a different program for your ipod eg Jriver media center
I know another way you could try formatting which may fix this problem. Restoreing just restores all the setting to your iPod yes it shoudl format as well but it may not due to an error or something.
To do try it another way follow these steps, first click on "Start" - "My Computer" look for you iPod when it's connect usually called "Removable Disk" once you've found it "Right-click" on it then click on "Format", once format is complete disconnect, then connect it again then run "Update" for your iPod and for iTunes, once you've done that have another attempt.
Good luck. Hope my solution was helpful in some way. Further problems leave a comment and i will get back to you.
Where did you download the songs? Napster?Rhapsody? Any online music stores? Try synchronizing them using their software. If you have ripped songs from a cd you may want to rip them again and before ripping them check this option on your windows media player software. Tools > Options then under RIP MUSIC remove the check mark that say's Copy Protect Music or choose the file format as MP3. Then format the device using the windows media player software(for version 10 = click on the sync tab then choose the pencil like icon on the far right, for version 11 = right click on the sync tab choose the player and choose format) use after doing that rerip the songs using the windows media player software.
Load the Philips software onto your computer.
You have to load the songs onto the player using WMP (Windows Media Player) 8 or 9.
Connect the player using the USB cable.
Run the Philips Go Gear Digital Audio Player software. Upgrade the firmware. This will format the player and erase everything you have done so far.
Start WMP. Click on the Synch tab.It will have 2 window panes. In the right side, at the top, there is a drop list. Select the player from the list.
Now create a synch list by clicking on edit playlist. Once you have added the songs, click Start Synch.
That's all there is to it.