All's Well That Ends Well is a problem of a play, and its hero, Bertram, is a bigger problem yet. Actors have often worked to make sense of this oddity of a character using Stanislavskian techniques, specifically "emotional realism", in order to create a Bertram that is relatable and believable, even though he's actually a fiction from a fairy tale. In this chapter we examine this approach critically in order to understand how the Stanislavsky Solution to the Bertram Problem can have a knock-on effect for the representation of the play's female characters, creating obstacles to understanding for contemporary spectators, and reinforcing unhelpful binary gender modalities.