One of the problems with William Shakespeare is that he is too familiar in our culture. The titles of his plays, and some of their basic themes and characters, are so well known, that we can hear the names of the plays without thinking about it, just filing it away under "Shakespeare stuff". It is why "Romeo" has entered our vernacular as a name for a womanizer, instead of as the name for a teenager whose obsession leaves him to suicide. And so it is with "All's Well That Ends Well", one of Shakespeare's lesser known plays: although the title is familiar, the play is less so. The meaning of the title might be so familiar that its meaning eludes people: because it translates, more or less, as "The Ends Justifies the Means".
This is one of Shakespeare's shorter and less character heavy plays. There are three characters who the play focuses on, with a few other supporting characters. The main characters are Bertram, a young lord; Helena, the orphaned daughter of a famous physician brought up as Bertram's foster sister; and Parolles, a dandy who acts as Bertram's friend, and acts as the play's comic relief and villain. The supporting characters include Bertram's mother, the King of France, a Clown, and a mother and daughter that Helena befriends. The plot of the play involves Helena, the daughter of a famous physician, having a cure for a disease that the King suffers from. He promises her that she can have her choice of husband from his lords if she cures him. Curing him, she asks for Bertram. Because she is not of the nobility, Bertram refuses her, instead going off to a war in Italy. Helena follows him, and meets Diana and her mother. She convinces Diana to seduce Bertram, then takes the place of Diana to seduce Bertram (The logistics of how they did this isn't explained in the text. Use your imagination). She then sends news to the court that she has died. Simultaneously with this, Parolles, who has annoyed Bertram's military advisers with his swaggering ways, is tricked into thinking that he was captured by the enemy, and then quickly and eagerly confesses military secrets and offers help betraying his comrades, in exchange for his life. When he discovers that it was a trick, he runs off in shame. In the play's final scene, back at the court of the French king, Bertram and Helena both appear, and she reveals that she is pregnant with his baby. And then, as the title suggests, everything ends...well?
While reading this, I had several questions. As people have noted, the type of activities that we find appealing in romantic comedies would be frightening in real life. But it hardly seemed that I could judge a play from the year 1603 (or so) by our modern standards of sexual and romantic propriety. Helena treats Bertram like a possession to be won, fraudulently has sex and conceives by him, and then brings her foster mother to grief by faking her death. But perhaps, in one of Shakespeare's comedy, this all falls under the things that a plucky heroine might do to win love. Along with manipulating Bertram, she also manipulates Diana and her foster mother, fitting them into her plans without seeming to consider their feelings. And while Bertram states that Helena's low birth is the reason for not wanting to marry her, she is also his foster sister, which might be a good reason for his aversion. Reverse the genders in this situation: a man pursues his foster-sister and through a process of manipulating everyone around him, tricks her into becoming pregnant by him. Even by the standards of the time, and even by the standards of fiction, Helena's actions seem highly suspect. This is especially in comparison with Parolles, who is criticized by everyone in the play for his total dishonesty. But despite being generally weaselly and unpleasant, Parolles doesn't do much, especially compared with Helena. And yet he is clearly the villain of the story, left at the end as a literally stinking outcast, while Helena is praised by everyone and married into the nobility. Two dishonest and manipulative people end up with very different fates. All's Well That Ends Well, which means you can do whatever you want, as long as you win in the end.
All of these thoughts while reading made me think I was missing the point, that I was perhaps applying 21st century values too zealously. But apparently, there have been several hundreds years of people scratching their heads at this play. It is called a problem play because it seems like neither a tragedy nor a comedy. It was apparently not popular during Shakespeare's life, and has never been one of his more popular plays in the four hundred years since. Although the reasons I mentioned are not the general reasons for people's ambiguity about the play (most commentators place the blame on Bertram, who is unable to appreciate what a good thing he has), the general reaction to this play seems to be that the pieces don't quite fit together, that the action is too contrived, and the characters just a shade too cynical.
I don't expect everyone to share my opinion or interpretation of this play, but I can say one thing that everyone should follow: once we shake out Shakespeare as just being "classical", of being something that we all know about as background knowledge, and start looking at the plays as discrete pieces to be read and understood, the possible interpretations in them expand and multiply.