How can I fix this iTunes problem?

Ditch iTunes and download MediaMonkey.

Do you listen to your songs all the way through? I noticed the same thing awhile back, and realized that some songs I would listen to most of the way through, but if they had a slow ending, I often skipped over the last part and went to the next song. If you do not listen to a song all of the way through, then it will not record as having been played.

@jeffgoldblumsprivatefacilities Yes I listen to the whole song. I don’t fastfoward them.

why do you care how many times you’ve listened to it?

Then I’m not sure. If you’ve reset the play count in itunes and figured out that it’s not itunes that is the problem, then I would try resetting your ipod (hold down the menu and central button at the same time) and seeing if that makes a difference. Good luck.

@JONESGH I actually don’t know, but I know something is wrong there.

@jeffgoldblumsprivatefacilities I’ll try it.

iTunes is big, clumsy, tries to do too much, and takes over your iPod. MediaMonkey just copies songs and playlists back and forth, along with ratings and song counts. Try it. It’s free.

I thought it always does that.

I reseted my iPod and nothing. It’s the same.
If I use MediaMonkey will I have to uninstall iTunes?

nope.

I didn’t want to start something else so I just stayed with iTunes. I deleted it then downloaded it again and did another reset. I’ll see if it works later on when I listen to it some more.