My 5th gen Nano won't Sync

Question

So, I have plugged my iPod in. On the actual iPod the screen says it connects and syncs, but none of my songs have gone onto it.
Itunes knows its plugged in, but pressing sync doesn't do anything.

Answer 1

To use automatic syncing, you need to set up the iPod's Music tab in iTunes, to tell iTunes what selection of songs to sync to your iPod.
Select the iPod in iTunes.  There is a row of "tabs" that starts with Summary.  Click on Music there.  On the Music tab, make sure Sync Music is checked.  Below that, you can select how to sync your iPod with music. 
If your entire iTunes music library will fit on our iPod, you can choose Entire Music library.  Otherwise, choose to sync Selected playlists, artists, albums, and genres.  Below that, make a selection of songs based on playlists, artists, albums, and/or genres (that will fit on the iPod).  After setting it up, click the Apply button to do the initial sync of your song selection to the iPod. 
Going forward, any changes you make to your iTunes music library (such as adding or removing songs) will sync automatically to the iPod the next time it is connected (or when you click that Sync button), but only IF the changes to the music library are included in your selection on the Music tab.
An easy way to set this up is to create a new regular playlist in iTunes, and call it something like "iPod Music."  From your main iTunes library, add only the songs you want on the iPod to that playlist.  On the iPod's Music tab, select that ONE playlist as your selection of songs.  Any time you want to update songs on your iPod, just update that playlist in iTunes and automatically sync the changes to your iPod.