During this song, John Mayer laments a failed relationship. Rather than moving on, the singer continues to brood over where they went wrong. He pins the blame on his ex over the first two verses, listing various "should haves" on her part: Shoulda been honest Shoulda just cried Shoulda told me there was nothing left inside
In verse three, Mayer admits to reacting angrily to his lover losing interest in him. One consequence of this was leaving hidden messages to her in some songs. I shouldn't be angry I shouldn't hold on I shouldn't leave messages in every little song Mayer dated Katy Perry on and off from 2012 until early 2016. Several tracks on his The Search for Everything album, including "Still Feel Like Your Man" are about their breakup. Some fans speculated this song is about the Californian pop star as well.
During the chorus, Mayer admits what happened in the past can't be changed and it shouldn't matter, but it does matter to him.
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