"Should've" by Empress Of is a song about regret and acknowledging the mistakes made in a relationship. The lyrics reflect on the narrator's decision to let someone get emotionally close to them, despite the warning signs and red flags they ignored. The repeated phrase "Should've never let you close" emphasizes the regret and realization that the narrator should have kept their distance. They admit that they should have recognized the other person's toxic behavior and not allowed themselves to become entangled in a destructive relationship. The lyrics also mention the presence of "sun in my eyes," which symbolizes a kind of blindness or lack of clarity regarding the true nature of the relationship. Despite the negative aspects, the narrator mentions that it could have been just one night, one kiss, and one fight for them to realize the other person's issues. However, they failed to see the signs and allowed themselves to sink deeper into the relationship. Overall, the song reflects on the regret of getting involved with someone who was not good for them and not recognizing the warning signs earlier. It serves as a reminder to be cautious and aware of the red flags in future relationships.