Songfacts®:

• The phrase "a square peg in a round hole" refers to somebody finding themselves in a situation unsuited to their abilities or character. When asked by Axs.com if she ever feels like a square peg these days, Kelsea Ballerini replied, laughing: "All the time, I still do. I feel like my whole life I have. Especially when I was younger, I struggled to find where I fit. For me, that message is just owning who you are and not worrying if you fit the mold. I feel like that's such a message I need to be reminded of all the time, so for me to sing it, is just for me to remind myself that. I hope other people get that as well."
• There are message songs as well as cuts about teenage romance on Ballerini's The First Time album. "I wanted to have songs about love, relationships and heartbreak, but I wanted to also have songs that were about life outside of boys," she told Billboard magazine. "The last two songs we wrote for the album were 'Underage' and 'Square Pegs.' I was in the mindset of wanting to write about something else."
  
  "I've always been drawn to the message of 'Be yourself. Love yourself.' I need to be reminded of that all time," Ballerini continued. "As a young female, I struggle with that. I think that writing that song was therapeutic for me. I get to remind myself and other people to be yourself, to rock you who you are and don't worry about if it fits."
• Though the expression "square peg in a round hole" is mostly of modern use, it was originated by the English Anglican cleric Sydney Smith in his 1804 lecture On the Conduct of the Understanding, one of a series of talks on moral philosophy that he delivered at the Royal Institution:
  
  If you choose to represent the various parts in life by holes upon a table, of different shapes, some circular, some triangular, some square, some oblong,—and the person acting these parts by bits of wood of similar shapes, we shall generally find that the triangular person has got into the square hole, the oblong into the triangular, and a square person has squeezed himself into the round hole. The officer and the office, the doer and the thing done, seldom fit so exactly, that we can say they were almost made for each other.
• Kelsea Ballerini wrote this with Josh Osborne and Scott Stepakoff. It was Stepakoff, who came up with the title. He recalled to The Shotgun Seat: "That morning I didn't have anything – I think I may have just like had that title written down – I just liked the sound of it but didn't know what it meant or anything, how to hook it."
  
  "I just started playing around with different clichés associated with square pegs, like square peg in a round hole, and started thinking about it, and square pegs make the world go 'round – I thought it was a cool sort of mixture. I was like, 'what if it's a song about people who are different?'"