Songfacts®:

• 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.
• John Mayer recorded this track for his Sob Rock album. It was the only cut he wrote for the record in his head rather than writing it down. "I'd stand in the shower and work on the song," he told Apple Music. "And then I went up and wrote it up in the studio in Montana. I wrote it in an evening. I just put it down, and I thought it was nice."
• Don Was (Bonnie Raitt, Rolling Stones) produced the track. Was has earned several Grammy Awards including the 1994 Grammy for Producer of the Year.
• Don Was produced seven out of Sob Rock's 10 tracks. "The songwriting on the record is decidedly modern - there's no throwback sensibility," the producer said to The Wall Street Journal. "As a musician and a songwriter, he's as good as anybody at finding something that's going on in his emotional inner life and expressing it eloquently."
• John Mayer debuted the song when he performed it on the July 15, 2021 episode of The Tonight Show Starring Jimmy Fallon along with "Last Train Home."