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I have a fantastic pair of headphones. But I just don't like wearing them.
When I was a kid listening to music in my parents' home, I lived inside headphones. Now that I can play anything as loud as I please, I never wear 'em. Sometimes, I check recordings I make with them - but I find that, even though music sounds fantastic with them - the fact that the sound is not traveling through the field of air in a room makes the sound quasi-unpleasant to me.
Anyways, sorry for the tangent - and for not properly reading the O.P. - I glossed over that your friend wanted to sync to their iPod. I still love WMP for playing everything I've ever thrown at it.
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