The album is the second part of a six-act story.[4]Act II begins with the death of the innominate main character's mother, Ms. Terri. Following her death, he travels to a nearby brothel in the hopes of learning more about his mother and the life she lived as a prostitute, as he himself was the product of her profession. He eventually finds love in a prostitute named Ms. Leading, but the relationship eventually falls apart due to his inability to cope with her chosen profession.
According to an interview with Casey Crescenzo for music website AbsolutePunk, the band wrote 120 minutes' worth of music for the album, but managed to trim it down to just under 80 minutes to avoid having to do a double-disc release.[4]
The album features numerous re-recorded tracks from the Dear Ms. Leading demos. Although Casey based much of the demo's lyrics on personal experiences, he has stated that the arc of falling in love with a prostitute is not based on any experience he's actually had.[4]
In June 2007, artist Kent St. John was selected to illustrate a book based on the story of Act II. The progress of his contributions can be seen at his personal blog.[5]
