 The lyrics of several songs relate to Duff's experiences between the releases of Hilary Duff and Dignity. The songs "Stranger" and "Gypsy Woman", despite speculation that they were written about Madden's then-new girlfriend Nicole Richie, were actually written about Duff's father's affair. She said that "Stranger" was written from her mother's perspective. "Stranger is a song I wrote about how my mom must feel around my dad," she said. "I made it seem like it was about a relationship I was in, because I didn't want people to know about my parents. But I 've realized that so many people can relate to what I've gone through." The album's title track has also been reported to be about Richie, though Duff did not deny rumors that it was. "Dignity is a song that is definitely about people in Hollywood", she said. "I wouldn't say that it is about her specifically but it is about people that kind of do what she does and act the way she acts." The song "Danger" was written about one of Duff's friends' relationships with an older man. "I understand that feeling of wanting to be dangerous," she said. "You may know morally something's not right, but you can't help yourself." She has stated that the song "Dreamer" was written about a stalker in a tongue-in-cheek fashion, and it has been speculated that it was written specifically about Miakovsky.
