Webb was asked to collaborate on the piece when only two songs, the title piece "Tell Me on a Sunday" and "It's Not the End of the World", had been written, so the rest was created specifically with her voice and character in mind. Black, who became her manager and a close friend, said of her performance, "She was 'the girl', and that was it." Her tendency to, "Talk for hours about the most boring everyday things, like the gas or insurance", also inspired him in creating the narrative pieces in the song cycle which were letters to the character's mum.