ITunes can't find the original file?

I have my entire iTunes collection on my iPod and, supposedly on my laptop. Yet every time I click on a laptop song, I get a message telling me that ITunes can't find the original song, do I want to look for it? I then have to run "Search", wait for the song to appear, and click on it to add it to my usable library. Then, I get two listings for the same song, and if I eliminate one listing, I get the "can't find original" message again. I have just under 60 gig of music and I don't want to search and add thousands of songs when they are already in there somewhere. I appreciate greatly any one's expertise in helping me solve this frustrating problem. Thanks!

Hi, Mike-D.
I'm assuming your music files are all in one centeral location - the iTunes Music folder or what have you.
There are a few basic strategies for dealing with your unfortunate situation:
1) Telling iTunes where the lost songs are on a one by one basis.
2) Moving the songs to where iTunes thinks they are. Unfortunately, there's no way to find out where that might be.
3) Start with a new iTunes library. Regrettably, this method will lose your playlists and related information (Ratings, Play Counts, Dates Last Played, etc.).
If that's not a deal-breaker for you, delete the current entries in your Library by highlighting them - iTunes Edit menu > Select All - and then right-clicking > Delete . You remove the entries from your Library but keep the files themselves in your iTunes Music folder, again that's assuming that's where they are in the first place.
You can then add them back into your Library by selecting the iTunes Music folder in Windows Explorer and dragging it into the Library entry in the iTunes Source List (left-hand column).

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