This song was written with Mann’s longtime collaborator and former partner, Jon Brion. Aimee Mann herself explains this song in the album notes to I’m With Stupid:

That’s a song I wrote with Jon. I wrote the lyrics. His plot instructions were: “When you and I broke up and we were trying to get back together and all my friends were saying, ‘Why would you go back to that nightmare,’ this song would be your answer to them.‘” The word amateur means you do things for love, but all the good intentions in the world don’t mean that things will go the way you want them to.