Songfacts®:

• This poignant reflection on heartbreak finds Carly Pearce looking back on her failed marriage to fellow country star Michael Ray. She filed for divorce in June 2020, eight months after their wedding.
• With the aid of hindsight, Pearce finds fault on both sides. She starts off the song by condemning herself for not learning from her parents' marriage.
  
  I am my mother's daughter
  I watched her with my father
  I saw it all, the good and bad
  Should've known better than that
  
  In the second verse, Pearce slates her ex for his part in the breakup.
  
  You sold me on a fantasy
  Damn, and it all felt real to me
  Thought you were the man in the photograph
  Should've known better than that
  
  Pearce explained the song came from her grappling with the breakup and finding accountability and perspective. "'Should've Known Better,' is kind of to me, as an adult, something that you probably wrestle with more of trying to not assign too much blame to yourself and also calling it is what it is," she said in a video. "I wanted to take both sides of it and show that a lot of times there are things that you overlook and there are things that maybe you, in the end, know that you should've known."
• Carly Pearce wrote the song with:
  
  Frequent Dan + Shay collaborator Jordan Reynolds, whose credits include "Tequila," "All to Myself," and "10,000 Hours."
  
  One of Pearce's go-to songwriting partners, Minnesota native Emily Shackleton. Their collaborations include "Every Little Thing" and "Show Me Around."
• This rage against a lack of intuition was the first song Pearce wrote for 29. The EP traces a period of Carly's life marked by two personal setbacks: the death of her mentor and producer, busbee, and divorce from Michael Ray. "'Should've Known Better' symbolizes the beginning of the grief," recalled Pearce to American Songwriter. "When you are dealing with some tough things in your life, it's easy to ask yourself, 'why didn't I know that this was going to happen?' It's no secret what I went through in the last year and a half, so I think people are like, 'How are you so able to put yourself out there?"
• Baring her soul on the record isn't exactly a new thing for Pearce; she started off her recording career with "Every Little Thing," which is about a guy who broke her heart. She then confessed in "I Hope You're Happy Now" about how she broke somebody else's heart.
  
  "I'm not doing anything differently," she told ABC Audio. "I'm honestly just telling my truth yet again, maybe a little bit more raw than even I knew I could do."