"Break My Heart Again" was released as a standalone single for digital download and streaming through Finneas' record label OYOY on February 9, 2018.

The sound of typing and sending messages is heard for the majority of the song: "Hey you/I'm just now leaving/Can I come around/Later on this evening?/Or do/You need time?/Yes of course/That's fine.

Finneas goes on to realize that he may be wrong for always allowing the former to hurt 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?

Finneas is pressured as he admits that he thought his lover was "the one", but their actions revealed that all they can do is break up and their relationship is over for good.

Kasey Caminiti, writing for DuJour, labeled the song as "soft" and "relatable", while further mentioning that it "highlight[s] the insanity of millennial love stories".

[8] Music Connection's Dan Kimpel commended the lyrical content and melody of the song, which he viewed as "gorgeous".

[4] Shaad D'Souza of Paper magazine stated that "Break My Heart Again" is a "traditional-sounding ballad", and complimented the "masterful production work" while opining that the listeners should "stay for the twists".

[10] The video was directed by Sam Bennett and choreographed by Monika Felice Smith, while it was shot in one black and white take.