"Should I Leave" is a heartfelt song about Buddy DML's relationship with Cayla. The two were going through a rough patch, not talking to each other as usual. Buddy DML decided to pour out his emotions in the song, but before recording, Cayla called him around 10:23 PM, expressing her anger but also revealing she knew Buddy DML felt deeply hurt when they weren't talking. Buddy DML reassured her that his actions were for her own good, and she forgave him the next day. Despite this, Buddy DML still recorded the song, pouring his soul into it.