Songfacts®:

• "How am I different?" is a good question to ask when vetting a potential boyfriend, especially one with a questionable dating history. Aimee Mann explained the story behind the song in the liner notes to the Bachelor No. 2 Or, The Last Remains Of The Dodo album:
  
  "I was being pursued by someone who had a history of being a terrible boyfriend and was trying to convince me that with me, it would be different. This is not unlike the experience of being wooed by a record company."
• The song is the first track on Aimee Mann's album Bachelor No. 2 Or, The Last Remains Of The Dodo. She was a rising star at the time, having released two acclaimed solo albums and also a trance of songs for the soundtrack to the 1999 movie Magnolia - her songs even served as inspiration for the film. But this was a down time for singer-songwriters, especially women. They just weren't trending in 2000, bumped aside by dance-pop (think Britney Spears).
  
  Mann was signed to Geffen Records, which was shifting management and had little interest in her album. So little, they offered to release her from her contract. She took the offer and put out the album on her own label, SuperEgo. The "Last Remains Of The Dodo" portion of the title is a reference to the extinct dodo bird, as she thought singer-songwriters were also facing extinction.
  
  The album ended up selling about 200,000 copies, which was quite profitable when people were still buying them for about $16. Mann emerged as a leading independent artist, free to make music on her terms.
• Mann wrote this song with Jon Brion, her main collaborator on the album. Brion is also known for his work with Fiona Apple and Mac Miller.