I have the Sena and yes you can share music. My wife or son, depending who is riding with me, likes to listen to their own music so we don't share. It's just a matter of paring up the headset with your bluetooth device.
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2013 RGC Candy Orange, 2005 Deuce (Traded), 1991 Sportster (sold),1948 Pan Head Hard Tail (sold and wish I didn't),1971 Honda 500 Four (original owner), Too many more to mention