The narrative centres on Eileen (McKenzie), a prison worker and the daughter of a former police chief, and is set in 1960s Boston (Shea Whigham). Four years into her job at the jail, Eileen is also caring for her perpetually inebriated father. When she first meets Rebecca (Hathaway), the prison's new psychiatrist, her life appears to be in a dead end, but she rapidly captures Eileen's attention due to her captivating personality. The two develop a friendship and then something deeper, but it doesn't take long for their relationship to change.

The actions Eileen does at the film's conclusion make sense given the development of her character. She has long suffered from the repercussions of her father's verbal abuse and drinking, which have made her a profoundly lonely person. But Rebecca's actions are what really catch viewers off guard, completely changing the plot and leading the movie down a different direction than it may have otherwise. The way Eileen ends is unexpected. It may be done to shock the audience and cause gasps, but that would be lying to what came before.

Both Rebecca and Eileen are compelling characters, but Rebecca is especially poorly written, and the connection between the two is more worse. Before the main revelation in the movie, there should have been more exchanges between them, but Oldroyd withholds more of them. Even the LGBT romance lacks depth and frequently comes off as constrained. Eileen's first half is meant to deliberately introduce the individuals and the place in which they dwell.

Even though Eileen is captivating, the movie ultimately fails. Its last scenes imply that it might have evolved into a whole different movie from what was initially shown. The final Rebecca twist would have worked much better if there had been more time to develop the plot and raise the stakes.

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