All’s Well That Ends Well is often described as a “problem play,” distinguished from the earlier, more cheerful comedies by unpleasant characters and a cynical treatment of relations between men and women, all capped off with a “happy ending” that is nothing of the sort. In a sense, these criticisms of the play are unfair. The characters in general are a pleasant group, distinguished either by the wisdom of experience (the King of France, Lafew, the Countess) or by basic decency and good intentions (Helen, Diana, the First and Second Lords Dumaine). Even the cowardly and treacherous Parolles proves sympathetic in the end, since he willingly acknowledges his own foolhardiness and resolves to go on while learning from his mistakes. The only truly unsympathetic figure in the cast is Bertram, who at every turn shows himself to lack the honor and virtue that are typically thought of as hallmarks of the nobility.

This is precisely where the problems of this “problem” play begin. Bertram is positioned as the romantic counterpart to our heroine, Helen. But despite Helen being the very picture of honor and virtue, Bertram treats her very badly indeed. He deceives her, abandons her, tries to seduce another woman, and only speaks kindly of her once he believes her to be dead. It is extremely difficult to reconcile oneself to a romantic lead as odious as Bertram, especially since he never seems poised for meaningful redemption. Although he does pledge to act as Helen’s husband in the play’s final moments, it’s only because he has no way out of the predicament he’s in. Her plot to satisfy the seemingly impossible conditions of his ultimatum has resulted in a situation where he is now “doubly won” (5.3.359), and therefore doubly cornered. Although some viewers might pity Bertram’s situation at the end of the play, Shakespeare has set him up as an unrepentant figure who lacks sufficient self-awareness to make a meaningful change in his behavior. Even the deceitful rogue Parolles turns out to have enough self-knowledge to be rehabilitated. Bertram, alas, doesn’t seem to follow Parolles’s example.

Meanwhile, the resourceful Helen cuts a far more appealing figure, and she’s loved by everyone—except, of course, for Bertram. The Countess and the King of France both see her as possessing an innate nobility of spirit, which is revealed by her eloquence and self-confidence, as well as the stick-to-itiveness she demonstrates in her devotion to Bertram. However, her relentless pursuit of a man who is obviously unworthy of her has the unfortunate effect of diminishing her appeal as the play goes on. Nothing stands in Helen’s way as she determinedly pursues the man she loves, and while we may admire her, by the time she appears triumphantly to show Bertram how he has been tricked, we no longer like her as much as we did. Indeed, it becomes increasingly difficult to respect her sense of taste as she refuses to waver in her longing for such a deceitful cad.

As the play draws to a close and Helen’s intricate plot to capture Bertram once and for all works toward its climax, few in the audience are likely to feel like love is poised to triumph. Helen may well repeatedly claim that “all’s well that ends well” (see 4.4.39 and 5.1.30), but it’s hard to embrace the apparently “successful” comic ending in which all tensions are resolved through marriage. Even the King seems unsure that things have ended well, which he indicates through the equivocating language of the play’s closing couplet: “All yet seems well, and if it end so meet, / The bitter past, more welcome is the sweet” (5.3.378–79). For a play that otherwise centers themes related to the nobility of spirit and the need for self-awareness, it seems rather cynical to conclude with a poorly matched marriage that’s disguised as a fairytale ending. The challenge of how to interpret the finale is, ultimately, the reason critics categorize All’s Well That Ends Well as a problem play. Is Shakespeare slyly questioning the theatrical conventions of comedy? Or is he perhaps doing something more radical and troubling the institution of marriage writ large? Alas, there are no easy answers.