Greta Gerwig excels in her performance of Florence, a 25-year-old living nearly rudderless in Los Angeles, working as a personal assistant for a wealthy family and barely pursuing a singing and songwriting career. Vulnerable and expressive to a fault, she falls into bed with men because it is easier to just go along than say no. She desperately wants to have a purpose and, since she cannot find her own, it seems that other people’s purposes for her are fine right now. When the Greenberg family offers to write her a check before they go on a long trip to Vietnam, she brushes the urgency of her bad financial situation to the side and insists she will come by the next day to pick it up after they have left.
This brings her into contact with Roger, the brother of Mr. Greenberg, who has come to live at the house while the family is gone. They have a strange first interaction, awkward and uncomfortable. But Florence insists that Roger call her for anything he may need.
Ben Stiller plays Roger Greenberg as a caustic, unlikable human being heading into what is definitely a wasteland of middle age (of his own making). He recently was released from an institution and has returned to Los Angeles from New York City to “do nothing,” as he says. He certainly embraces the situation. His brother and family have gone away for six weeks and left him with the house and dog. He spends his time composing letters to various organizations he feels have wronged him in some way, one being United Airlines for having a seat reclining button that did not work to his liking. He calls an old band mate (Rhys Ifans) and has the kind Brit drive him around and listen somewhat patiently to his constant criticism of every detail the world has decided (in his mind) to assault him with.
Roger does call Florence and suggests they go out for a drink, more out of boredom than any attraction. They end up instead at her apartment, sharing the single Corona in the fridge. Roger makes a strange pass at her that she, at first, does not deter. Then, as he lifts up her skirt, she becomes skittish. She reveals that she has just come out of a long-term relationship and is afraid of simply going from “having sex to sex to sex.” “Who’s the third sex?” asks Roger Greenberg. Florence blinks. “You.”
It seems that Roger isn’t just having trouble getting laid. The story reveals that his old band had been offered a big record deal back in their heyday that Roger flatly refused, much to the sorrow of the other band members. This bad decision colors his interactions with all his old acquaintances. Everyone is still mad at him for abandoning what should have been instant success simply because he didn’t buy into big labels. They’re right to keep up the anger. Roger doesn’t appear to have any idea what he did to the people who had been around him.
But Florence is different. She is younger and impressionable. She thinks Roger is a sensitive and thoughtful human being. He easily pulls her back into some sort of weird semblance of a relationship. They keep ending up pulling each other’s clothes off. But every time it seems like things are going somewhere good, Roger keeps pushing her away. Roger Greenberg makes it almost impossible to like him, even for someone, like Florence, who wants to like everyone.
It isn’t an easy task to watch Roger’s interactions without hating him. He has so closed himself off from sentiment that all he can emote is anger at a world that has (somewhat rightly) rejected him. An easier film than Greenberg would shove in some sort of epiphany for Roger to realize and give him time to apologize fully for his many transgressions, begin to heal. He and Florence would certainly end up together. However, Baumbach does not have redemption for his lead character in mind. It is something more realistic, humane and also touching. This is a man who, despite every effort to the contrary, can be loved. Unfortunately, he cannot find it within himself to return that love.