Fiona called this backwards love ballad, "thinking about how did I get here," at a showcase for The MF Life in New York. It is one of a number of tracks on the album, in which she sings of heartache. Fiona wrote the songs when she was in the middle of a happy relationship, which later ended. She explained to The Boombox: "I actually wrote all the songs that I ended up living, before I lived them, which is really crazy. I found myself with all the records that I wrote in succession and they actually told the story of what happened in that relationship. I was in the relationship and at the time; I didn't foresee it ending."
Asked by The Boombox how she can write from a place of heartbreak when in a happy relationship, Fiona replied: "I think that subconsciously our emotions get the best of us even though we consciously don't necessarily recognize them. For me - frustration, sadness, despair, anger - these are the things that help me write my best music because I feel that I'm a positive person overall. My outlet to express that darker side of me is through my music. I don't necessarily have to live that everyday but it's therapeutic for me to get it out. Oddly enough, it's not just me, the singles that become the hits are the ones that people choose. It seems that there are a lot of people going through heartbreak and just need a voice to help them say it. You live and you learn. I moved on from 'It Kills Me' and now, we'll get through 'Wrong Side of a Love Song.'"
According to the NY Post the guy whom Fiona was dating whilst writing the songs for the album was CSI:Miami actor Adam Rodriguez. The couple were in a relationship for three years before splitting while the Canadian singer was recording The MF Life.