Songfacts®:

• Natalie Merchant wrote this song of encouragement for her second solo album, Ophelia. In her 2005 VH1 Storytellers appearance, she talked about writing it. "I wrote this song 'Break Your Heart' for a lot of the young people that I know, 'young' being under 22 - I consider that young. And I just wanted to acknowledge to them that I understand that we reach a point where our innocence is lost, no matter how sheltered our lives may be. We reach a point of a certain amount of disillusionment when we realize that people struggle and they despair and they can be, at times, cruel and selfish.
  
  And the lesson to learn from that, hopefully, is – pardon me if I get didactic for a moment and talk about lessons – but is that even though we're surrounded at times by hopelessness or helplessness that we shouldn't feel like we have no hope and that we can't help.
  
  So, that's what 'Break Your Heart' is about.
• N'Dea Davenport of The Brand New Heavies sings on this track with Merchant.
• In the video, Merchant is seen carrying a bag of groceries up a set of stairs, while Davenport tries to navigate them with a baby and a stroller. Oblivious people bump into them and knock over Merchant's groceries, but in the end, they help each other out and find support.
  
  The clip was directed by Sophie Muller and shot at the Chelsea Hotel in New York City.