Every time i plug in my iPhone 5 the same song alphabetically gets played. This annoys me to no end to be listening to music in my headphones then plug my phone in only to be reset to the same song every time. Why does this happen? Is there a setting i'm missing? 

Mine does too and I have the 4s. Then I can go into the songs and select a different song and it will shuffle differently then. But then next time the same songs again. I have no idea what happen to real "shuffle"

I too was anoyed with this issue for a while. I now just set the ipod to shuffle songs before I plug in.

You can also change the setting with the toolbar at the bottom of the screen.