IPod starts with same song in car

I use my new iPod for music when I drive my car. Whenever I plug my iPod into my USB port, it always starts off playing the same song, which happens to be the first song on my list. It's so annoying. I do have my songs on shuffle. All I have to do is press next and it starts shuffling fine.
By the way, this never happened with my iPod Nano.
Is there any way to get my iPod to shuffle a random song instead of it playing the one that is first on the list? Any help?

I discovered on the radio itself that there is a Repeat Button on Button #6. I stumbled on it by accident...it wasn't in the User's Guide. Guess I answered my own question!

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an ID3 Tag is the data that is used to properly identify the music that is playing on the track. For instance, if you have a song playing on your iPod, it'll tell you the song name and artist, and what disc it's on. That's what the ID3 Tag is responsible for. Otherwise it'd just read the filename of the track and call it like that. No organization whatsoever.

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First, try a system reset. It cures many ills and it's quick, easy and harmless...
Hold down the on/off switch and the Home button simultaneously until the screen blacks out or you see the Apple logo. Ignore the "Slide to power off" text if it appears. You will not lose any apps, data, music, movies, settings, etc.

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I had the same problem with my iPad, i couldn't get the newer version of itunes because the computer was too old and my iPad couldnt sync with the old itunes. I got a PC from school a few months later so that solved the problem for me. Unfortunately i don't think there would be a program to put your music on your iPod, iTunes should be the only way to transfer files to Apple devices. What operating system are you running and what version of it is it?

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Make sure the repeat setting is turned off. For mor help, see your iPod's User Guide.
http://manuals.info.apple.com/en_US/iPod_nano_6thgen_User_Guide.pdf
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Is there a way to change that?

I haven't tried restoring it yet. I thought there
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Why is it that my wifes shuffle (1st generation) always starts with the same song even though it is set to shuffle mode? It is driving her crazy that every time she turns it on to listen the shuffle starts with the same exact song & then plays them in the same predictable order rather than truly shuffling the songs each time she turns it on. Any advice? It be greatly appreciated & will help her sanity.
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Why is it that my wifes shuffle (1st generation)
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set to shuffle mode? It is driving her crazy that
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starts with the same exact song & then plays them in
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My iPod always resets itself at the same point of the same song without fail. I've manually reset the iPod, resynched, and still the same result. Before I delete the track and redownload, has anyone ever encountered this? This track plays fine in iTunes by the way.
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As mentioned, you need to be using the correct iTunes version (iTunes 7 or later for the 2nd gen nano). Also, have you tried going through the "5 R's"? If not, you need to try them. Save the restore for last.
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How To Use Multiple iPods with One Computer
You can read more about playlists at these links:
iTunes: Creating playlists of your favorite songs
How to create a Smart Playlist with iTunes
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IPod starts with same song in car

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