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I'm not sure, b/c I'm 'kind of' new, as well....but do you have Windows Media Player open first? You have to make sure that you have the app that plays your movies open, then go to 'Open' or "Library' from that application.
Sorry if you already knew this... It was the only thing I could think of...
-Touche'
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Now: HTC Evo 3D
Then: PPC-6700 -> Mogul -> Touch Pro -> Touch Pro 2 -> HTC Evo 4G
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