As Brandon Lancaster started writing the song he began to reflect on some of his experiences, including how he met his now-wife, Tiffany Trotter. He explained to The Boot
"I'm married now. I had been dating my wife since I was 19, so it wasn't necessarily high school. We had been together a long time, and took some time apart and broke up and got back together.
The foundation of the song was from my life. I took some stories and some characters from my experiences growing up in Smyrna, [Tennessee], and some friends I had, a little bit of their story, and kind of put it all into one song. It's cool, because it's an ode to songwriting being both experiencing and observing, so that song has both of those things in it.
Love is about compromise, and it's about meeting each other in the middle and learning about each other and learning about yourself through that person. One thing that's cool is, I think, now that I'm married – 'Greatest Love Story' is kind of about the story of that journey of finding love and finding that person, but now, being married, it's the beginning of another story, the beginning of another chapter. It's the end of one chapter, the beginning of the other, from a songwriting perspective."