Few of Shakespeare’s works offer such a sharp contrast between two generations. The older characters in the play are haunted by death: the Countess has lost a husband and is aging herself; Helen’s father has passed away; Lafew is infirm; Diana’s mother is, appropriately enough, a Widow; and the King is near death as the play begins. In a sense, the shadow of death makes this a very realistic work, since the younger generation—Helen, Diana, and Bertram—are at an age for marriage, and, given the life expectancy of Shakespeare’s time, few people lived to be grandparents. But if the old people are haunted by death, they are also graced with wisdom and discernment: they all see through Parolles, perceive Helen’s worth, and condemn Bertram’s immaturity. The younger generation, while not unsympathetic, lacks this wisdom: Helen is intelligent, but her love for Bertram is misguided; Diana is naive and inexperienced; Bertram is callow, arrogant, and spoiled. The prospect of these characters inheriting France from the gentle wisdom of the Countess, the King, and Lafew is a disheartening one.
Like all of Shakespeare’s comedies, the plot of All’s Well That Ends Well is primarily concerned with bringing young people together in marriage. It is not, however, a romantic play: relations between the sexes are relentlessly demystified. The good characters, like Helen and Diana, are moral, defending female virtue and monogamy against the lechery of Parolles and the adulterous advances of Bertram. However, they are also cynical about the opposite sex. Helen is “in love” with Bertram, but she seems unconcerned by the fact that he does not love her back, busying herself instead with trapping him into marriage—first through the King’s command, and then by tricking him into sleeping with her. Though she laments how men “can such sweet use make of what they hate” (4.4.24), she also uses this deficiency to her own advantage. The audience may applaud the resourceful ingenuity of her plotting, but we can’t truthfully say that her ultimate union with Bertram has anything of romance in it. In the end, then, marriage emerges as a mere convention that coerces an unmatching pair into an ambiguous union.
Parolles is a boastful, cowardly, and treacherous character. Bertram’s unpleasant qualities have occasioned some critics to argue that it is Parolles who leads him astray, and that he is therefore the villain of the piece. But such a claim overestimates Parolles. Other Shakespearean villains, like Iago in Othello or Edmund in King Lear, are masters of deception, but Parolles is no such thing; he is eminently transparent, and virtually everyone sees through his bluster. Bertram’s failure to do the same is therefore a sign of his lack of perceptiveness. This lack is corrected in the humorous scene where he is made to believe that he is a prisoner, and, blindfolded, proceeds to betray his supposed friends while they look on and laugh. Yet Parolles’s role in the play isn’t just for comic relief. His public chastening foreshadows a similar dressing down experienced by Bertram in the final scene. In a strong sense, Parolles also offers of model of how Bertram could be redeemed. Parolles accepts his punishment, but he doesn’t disappear from the play. Instead, he returns to Rossillion and becomes a servant to Lafew. It’s a minor redemption, but it’s one made possible by Parolles’s capacity for self-awareness. If Bertram can find similar self-knowledge, he too can be rehabilitated.