i think it's about a relationship ending and he uses the ideas of jail, handcuffs etc to also express the relationship he still loves her she has left him. "free with a history" meaning she is now free and she has a history with him and that will never go. she is free from jail and has a history is another look at it. but this title explains it all it's always harder now that it's over. a sad song that i can relate to and i'm sure many others can as well.
i think it's about a relationship ending and he uses the ideas of jail, handcuffs etc to also express the relationship he still loves her she has left him. "free with a history" meaning she is now free and she has a history with him and that will never go. she is free from jail and has a history is another look at it. but this title explains it all it's always harder now that it's over. a sad song that i can relate to and i'm sure many others can as well.