Genuine emotion is hard to portray in film, especially when the emotion is grief. For writer/director Brad Silberling, Moonlight Mile was a labor of love. The film deals with the three people dealing with the death of a woman; her parents and her fiance. Silberling was in a similar predicament a while ago when actress Rebecca Schaeffer was murdered. Moonlight Mile is not exactly autobiographical, but surely draws on his experiences, and because of them Silberling (City of Angels, Casper) is able to convey a deeper range of emotions than somebody else could have. The movie starts after the funeral. Joe Nast (Jake Gyllenhaal, The Good Girl, Lovely & Amazing) is living with the Floss'. Originally, he was to go into business with his new father-in-law.

Awkwardness is the main emotion present. All three people are hanging on to the memory of their beloved, and going about it in different ways. JoJo (Susan Sarandon, The Banger Sisters, Igby Goes Down) is the type of person who says what is on her mind. She is a writer, but currently has a serious case of writer's block. She is sick and annoyed with everybody constantly asking how they are feeling and offering their help. Ben (Dustin Hoffman, The Kid Stays in the Picture, The Messenger) copes by throwing himself into his work, and acting like nothing is different. Joe has the hardest time. He is harboring a secret, but feels so obligated to help the Floss' hang onto the memory of his daughter, that it seems like he is afraid to do anything else. He has no real desire to go into the real estate industry with Ben, but goes along because he doesn't know what to do.

Things change drastically when Joe meets Bertie Knox (Ellen Pompeo, Eventual Wife, In the Weeds), a young woman going through something similar to what he is. The two are drawn to each other, since they understand each other deeply. This poses a huge problem for Joe. He feels a loyalty to Ben and JoJo, and a relationship with Bertie is like betraying them. He is torn between his feelings towards Bertie and his desire to honor Ben and JoJo. The performances are what make Moonlight Mile a strong movie. There are three Academy Award winners in the movie (as every trailer touts) but Gyllenhaal gives the strongest performance. In fact, this is his strongest performance to date. Joe is cautious, unsure, and completely confused as to what to do. He is kind enough to put the thoughts of others above his own, even it may be detrimental to him. Pompeo is also good in a fresh role.

Some of the story elements in Moonlight Mile drag it down. In Bounce, there was an unnecessary court drama that seems randomly inserted into the third act. Its main purpose was to allow one of the characters to give an emotional speech that brought the movie together. The same thing happens here. The courtroom third act does not mesh well with the tone of the movie, and the monologue that comes with it is ill suited. Silberling could have placed it somewhere else with better results.