"I Wish I Could Break Your Heart" is a song by recorded American country music singer Cassadee Pope, written by Gordie Sampson, Ashley Monroe and Jon Green.

[1] The song was written in 2012 as a creative collaboration between Nashville songwriters Gordie Sampson, Ashley Monroe and Jon Green at the former's writing room, The Shack, with no particular artist in mind.

[2] The song's title came from Monroe early in the process, providing the writers a premise and emotional angle to work with.

According to songwriter Ashley Monroe, the song is told from the perspective of someone who loves their partner too much to actually want to hurt them but still wishes they "had the power to".

[2] The music video for "I Wish I Could Break Your Heart" was directed by Wes Edwards and premiered February 18, 2014 on CMT, before being released onto Vevo the following day.