Commentary on the issues of gender and desire necessarily centers on the character of Helena, although some mention of Bertram is warranted as he is directly involved in what some critics call the reversal of gender roles in the play. More recent critics focus less on whether Helena was justified in her actions—bartering with the King to gain Bertram as a husband, following Bertram to Italy, engaging Diana in the bed-trick to fulfill Bertram's otherwise impossible conditions and thus tricking him—and instead confront such issues as Helena as subject rather than object, as desiring rather than desired, as pursuer rather than pursued, and she embodies both activity and her passivity.
Several critics note the similarity between the masculine quest-romance or the theme of the knight-errant and the plot of All's Well That Ends Well, only in the latter the initiator of action, the savior, the hero, is a woman. Helena possesses the knowledge and skill to influence events and other characters and thus is able to secure Bertram as a husband. However, she cannot force him to love her, and his repudiation of her necessitates her pursuing an alternate plan of action. Some critics note that Helena's active role, her ability to go out and get what she wants (Bertram), is motivated only by physical, sexual desire. Others excuse her perhaps unorthodox means of fulfilling Bertram's conditions because they were created with the intent of being impossible to fulfill and because she had no other recourse after having been publicly humiliated by Bertram.
Some commentary takes note of the dual nature of Helena's character— she has elements of both the "traditional," passive female character and the more "masculine" active character. Helena, as desiring subject, sets out to gain Bertram for a husband by curing the King. Yet when it comes time for her to select a husband as payment for curing the King, she emphasizes her low social status and how unworthy she is. When Bertram rejects her and humiliates her in front of the entire court, she retracts her choice. When Bertram leaves her to go to the wars in Italy, for a time she passively sits at home and then wanders off as a pilgrim so that Bertram can remain unfettered. Even when Bertram sends the letter with the conditions of his acceptance of her as his wife, conditions that he believes she could never fulfill, Helena is not angered but takes pity on him instead, noting how she "stole" rank by...
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