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is there any error message pop up when playing youtube videos? you can install a plug-in software to download and convert youtube videos you like. Like WinAVI YouTube Download or WinAVI FLV Converter..... Some introduction on: http://www.winavi.com/flv-converter/index.htm u can first check and then download for try.
i think you can download the video from youtube first will be better. And I have used a youtube downloader for long,it can not only download videos from youtube but also convert videos to the right format for your iphone. here is the link for the Free youtube downloader.
this phone does not support flash player so you may be running into a problem there .if you cant watch youtube try downloading the app from the market on our phone if its not available then your phone dosent support video of anykind