In the movie, Michael Shannon plays Dane Wells, Laurel's police partner and straight friend to whom she is closeted until she no longer has a choice. But if Laurel had underestimated him, she soon realizes how much of an ally he wants to be. Rounding out the main cast, Josh Charles plays a sympathetic Freeholder and Steve Carell breaks type as a brash LGBT activist who takes up Laurel's cause.

Sollett spoke of the three lead actors' different approaches. Moore was "research-oriented, and took the beautiful documentary and the journalism that was available on the subject and really internalized it." He said, "She made it her mission to become an expert on the life of Laurel Hester. And it infused her choices within the scenes, and this is an important guiding light for us because it kept us honest." To play Dane, Shannon spent time with Wells, who was often on set. "It was really Dane's warmth that I think brought Michael to such a large-hearted performance — the type of charismatic performance that I don't think people expect of him," Sollett said.

When he first met with Page, who is also a producer on Freeheld, she asked Sollett what he thought the movie was about. His response was simply: "It's a love story." In her role as Stacie, a mechanic who falls in love with the older, but less out Laurel, Sollett said, "With Ellen, an actress we know and love and I think audiences completely embrace, I don't think it's wrong to use the words 'breakthrough performance.'"

"She feels different, her physicality is different — the transformation is new," Sollett said of the actor, who came out in February 2014. "That was thrilling. She was incredibly excited about that; she was being more honest. I think she was exposing more of her personal life, more of herself."