Much of the plot of All’s Well That Ends Well hinges on Helena’s willingness to dismiss the constraints of her traditional, feminine gender role. Because Helena subverts her own prescribed gender role (mainly, that a woman should be demure and not exhibit unprompted sexual interest in a man) in pursuing her heart’s desire, Bertram is also forced against his will into a reversed gender role by becoming the pursued. Her other actions are also quite bold for a woman. She engages in a frank discussion about her virginity with Parolles but is adamant about remaining a virgin, thereby embodying both gender roles of participating in a sexual debate with a man while remaining chaste. She travels alone to Paris, heals the king (traditionally a male job), and thereby is allowed to choose her husband, a complete subversion of normal gender roles. She also leaves Rossillion and travels on a very long pilgrimage all by herself, arranges the bed-trick for her own benefit, and craftily stages her own death in order to get what she wants. However, also implicit in her proactive role is a desire to engage in a more traditional role. She longs to be desired by Bertram and to have his child. In the sense that both of these happen at the end of the play, all does end well for Helena.
This dual nature of Helena’s character, in which she exhibits elements of both female passiveness and masculine action, is demonstrated in the scene where she selects Bertram as a husband. She emphasizes her low social status to the king and how unworthy she is. It could be that she is only playing up her feminine side in order to seem more attractive to the assembled suitors. But when Bertram rejects and humiliates her in front of the entire court, she retracts her choice. The marriage proceeds only because the king insists on keeping his word. When Bertram leaves her—their marriage still unconsummated—to go to the wars in Italy, she passively sits at home and then wanders off as a pilgrim so that Bertram can return to Rossillion. In a sense, this is a passive act in that it reveals her sense of defeat. 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 marrying him. Finally, once Helena has completed the tasks Bertram required of her and he takes her as his wife, she is satisfied with the role of wife and mother, which will presumably place her permanently back in a more traditional female role.
Several critics note the quest-romance and the knight-errant themes in All’s Well That Ends Well, only in this case the initiator of action—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 rejection requires her to pursue an alternate plan of action. Some think that Helena’s active role, her ability to go out and get what she wants (Bertram), is motivated only by sexual desire. Others excuse her unorthodox means of fulfilling Bertram’s conditions because they were created with the intent of being impossible to fulfill. Thus, she had no other recourse after having been publicly humiliated by Bertram than to arrange the bed-trick.
(extracted from) Shakespeare for Students:Critical Interpretations of Shakespeare’s Plays & Poetry, Second Edition, Volume 1, authored by Anne Marie Hacht & Cynthia Burnstein, published by Thomson-Gale, 2007