Hi Derek HadleyD,
Follow these steps:
a) Plug the iPod Nano into the computer using the Nano's USB cable.
b) Click on the "Start" menu, select "All Programs" and choose "Windows Media Player."
c) Click the "Sync" button on the menu. Windows Media Player shows the iPod Nano in the top right corner as the device to transfer music to.
d) Click and drag files from the music library in the middle of the screen to the "Sync List" area on the right where it says "Drag items here." Drag songs individually or by entire albums or artists. Select specific songs from an album list by holding down the "CTRL" key while selecting songs and then dragging one of the highlighted items to the Sync List.
e) Click the "Start Sync" button beneath the Sync List to start syncing. When the sync process finishes, disconnect the iPod Nano from the computer.
For reference: