When Tori Amos had a miscarriage, she says that she felt like the baby had rejected her because she wasn't a good enough person to be a mother. It may not make sense logically, sure, but emotions often don't, especially with traumatic things like that.
"Playboy Mommy" was based on that, being written from the perspective of a war-time prostitute who also lost a child and has similar feelings about it, that her little girl was ashamed of her, but hopes that when her child goes to "cross that bridge" into the afterlife, the spirits of the soldiers that she was with will be there to help her along the way because she was "a good friend" to them.
It makes me tear up a lot in general, but then recently when I heard it I thought of Emma and the Hellions and I JUST BASICALLY DIED SOBBING
(Note: I am not calling Emma a prostitute. That should not even be an insult, but people like to use it as one, especially against women who make the clothing choices Emma does, because people suck. That part is not what reminds me of Emma and the Hellions, it's the concept of a woman feeling that she lost her children because she was a 'bad person' in some way.)