Break My Heart Again

"Break My Heart Again" was written and produced solely by Finneas.[1] It was released for digital download through his record label OYOY on February 9, 2018.[2] In an interview with Atwood Magazine, Finneas explains that "New Girl", "I'm in Love Without You" and "Break My Heart Again" were "all these songs that from the moment I started writing them to the time I recorded them it was a short period of time because I usually get obsessed with things like that and normally whatever else I had planned for that day goes out the window, if I feel like I have an idea I have to finish".[3]

According to sheet music website Musicnotes.com, "Break My Heart Again" runs "with a smooth flow" tempo at 72-76 beats per minute (BPM) and is played in the key of G major. Finneas' vocals range between E₃ to D₅.[4] Musically, "Break My Heart Again" is a ballad that features a more indie-pop sound compared to Finneas' usual electronic productions he creates with his younger sister, Billie Eilish.[5][6] It features minimalist production that consists of a piano.[5] Finneas sings about his interactions with someone he loves and how they take advantage of him: So go ahead and break my heart again/Leave me wonderin' why the hell I ever let you in/Are you the definition of insanity/Or am I/Oh, it must be nice/To love someone who lets you break them twice".[5][3] As the song comes to an end, tensions rise as he and the one he loves fight. Finneas reluctantly ends the relationship, saying it was not meant to be.[3]

Modestas Mankus of Our Culture Mag called the song an "emotional and attaching piece that grows on you as it progresses with its subtle touches and its genuineness".[7] Alissa Arunarsirakul of Ones to Watch commended the lyrics and instrumentation, saying it has "delicate" piano and "passionate" vocals.[5] Nicole Almedia of Atwood Magazine said it is "not only a soothing song for the brokenhearted, it is also proof of O’Connell’s supreme talent".[3]

A music video for "Break My Heart Again" was released to YouTube on April 18, 2019,[8] and was shot in black and white.[5][6] The video was directed by Sam Bennett and choreographed by Monika Felice Smith,[5][6] while shot in one take.[5] The clip opens with the camera turning around Finneas as he sings about getting hurt by the one he loves.[6] As the song continues, Finneas starts tugging and pulling on his shirt, portraying how painful it is for him to let go of someone who means a lot to him.[5][6] Alex Darus of Alternative Press called the visual a "heart-wrenching black and white video that really put us in our feels".[9] In April 2020, Finneas performed "Break My Heart Again" during a 50-minute livestream for Verizon Communications.[10][11][12]