Dumb question about transferring selected songs to my iPod

Sorry if this is very basic, but I have more songs on iTunes than can fit on my iPod. I thought I could choose the songs that I wanted to transfer by unchecking the ones I wanted left behind, but instead iTunes randomly selected songs to trasfer from my library, ignoring my check/no-check. So now I have songs on my iPod I don't want there, and I don't have songs on it that I would like. Any thoughts, iPod experts? Your help is appreciated.

Welcome to Apple Discussions!
Connect the iPod to the computer and go to edit-->preferences in iTunes when the iPod appears in iTunes. Click the iPod tab. Check only update checked songs. Then click automatically update all songs and playlists. (And make sure only update checked songs stays checked). Click OK.
You could also make a playlist of the songs you want and have iTunes sync from that.
btabz

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