Meaning of "That's How I Knew This Story Would Break My Heart" by Aimee Mann

The lyrics of "That's How I Knew This Story Would Break My Heart" by Aimee Mann depict a sense of foreboding and melancholy in a failing relationship. The imagery of exchanging drawings symbolizes communication and connection between partners. The anchor tattoo on the partner's face suggests a sense of being weighed down or trapped, while the narrator's bird drawing represents freedom but with an underlying fear of confinement. The reference to an exit being crude but necessary hints at the difficulty of leaving a relationship that is no longer fulfilling. Ultimately, the narrator recognizes the signs early on that this relationship is headed towards heartbreak, but they feel resigned to the inevitable outcome. The song conveys a sense of resignation, acceptance, and emotional detachment in the face of impending pain.