HT1688 Why will some songs from my iPhone not transfer onto my iTunes & vice versa?

I've had the same phone for about a year and a half and it's always been fine up until a few months ago. Some songs just show up in iTunes but are shaded and there's a little circle all the way on the left side of the row. I'm not sure why this is happening and it's rather frustrating. Any suggestions?

Should've mentioned in your post.
Now try de-selecting all the songs in iTunes, and sync.
Do a Reset: Hold down the Sleep/Wake button and the Home button at the same time for at least ten seconds, until the Apple logo appears. Note: You will not lose any data
Select the songs you want and sync again.

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