Lyrically, "Heartless" features West's forceful and direct reflection on breaking up with his ex-fiancé Alexis Phifer.[20][27][28] He expresses honesty and self-pity on the chorus: "The coldest story ever told / Somewhere far along this road / He lost his soul / To a woman so heartless".[21][29] West also asks a question angrily twice before the chorus finishes: "How could you be so heartless?"[21] Self-doubt is expressed on the song by West, who raps that despite having "homies", he is ultimately "still so lonely".[26] West goes on to shed light on the post-breakup phase, assuming that Phifer will realize she is never going to find anybody better than him after two months.[30]