Kate Winslet and Josh Brolin agreed to do the movie, but Jason Reitman and Brolin had to wait for Winslet for over a year to begin shooting.
Director Jason Reitman commended Kate Winslet for her immense preparedness and total commitment to the character. "I don't know another actress who knows how to deal with this kind of brokenness and vulnerability and make it so sensual." He observed that her script had more notes on it than his did.
Kate Winslet felt very protective of Gattlin Griffith throughout shooting, especially on his first day. "He was terrified. I just said to him, 'You're really nervous aren't you? Well, so am I, and so is Josh and so is Jason.'" Jason Reitman recalled watching Winslet and Griffith having conversations in between takes, not just of the film, but acting in general.
Because of a pivotal scene, Paramount partnered with the American Pie Council in the promotion of the film.
Jason Reitman prepared his cast and crew by screening them films he considered relevant to the project. These included Conta Comigo (1986), O Peso de um Passado (1988), A Árvore da Vida (2011), O Mensageiro do Diabo (1955) and Corpos Ardentes (1981).
Joyce Maynard: Author of the book 'Labor Day' appears in the store with Kate Winslet, before the titular labor scene.