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Though originally the play was classified as one of Shakespeare's comedies, the play is now considered by some critics to be one of his problem plays, so named because they cannot be neatly classified as tragedy or comedy. It is not among the playwright's most esteemed plays, with literary critic Harold Bloom writing that no one, "except George Bernard Shaw, ever has expressed much enthusiasm for All's Well That Ends Well."

To director Karla Hendrick, the play's quick shifts in tone are Checkhovian and that is the source of its strength and beauty. She explains that the play might seem to depict a smart woman who falls for the bad boy and makes dumb choices. But viewed through the healing power of the feminine, it becomes a discovery of becoming a woman and what it means to become a man.  

Helena, on her journey of self-discovery, is driven by her heart and a positive life philosophy. She makes bold choices and is emboldened with each success.  Bertram is on a journey too; becoming a war hero and learning what it means to be a man.  The play, then, is a Checkhovian coming of age story of two young people united through diverse journeys through despair and darkness.