"How Could an Angel Break My Heart" is the fourth and final single from Toni Braxton's second studio album, Secrets (1996). The song, co-written by Braxton and Babyface and produced by Babyface, features Kenny G on the saxophone. At the time of this single's release, Secrets had reached eight-time platinum status by the RIAA.

The fact that the single did not manage to chart on both the Billboard Hot 100 and Hot R&B/Hip-Hop Songs charts was a surprise for fans and observers. However, it was potentially influenced by the fact that two of the three singles released from Secrets prior to "How Could an Angel Break My Heart" were double A-sided and their flipsides had also turned into essentially huge airplay hits. This means that at the time this single was released, Braxton had already dominated the charts with five songs from the same album, therefore radio programmers put very little emphasis on the sixth.

The music video, directed by Iain Softley, followed the lyrical content of the relationship between Braxton and her lover. He has left her for a Caucasian woman and she is left to pick up the pieces.

The remix version of the song has the storyline laid out a little differently, with Babyface singing back to her and duetting with her from the second verse. Babyface's vocals replace Kenny G's saxophone parts.

This CD has an error in the tracks. Despite being listed in this way the two instrumentals have been put on in the reverse order. This can be heard clearly as Kenny G's saxophone parts are present on track four and absent in track three, whereas in the vocal versions of the song, this is quite the opposite.

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