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Critical formulations of Helena, the main protagonist of All’s Well That Ends Well, has been radically diverged into either negative or positive portrayal of the character. Even among feminist scholars Helena’s problematic character has been seen either to downrightly subvert the patriarchal values of the Elizabethan-Jacobean society or to adroitly serve to reaffirm them. The critical debates are premised on the interpretation of the character’s blurred motivations and the play’s structural ambiguity on the one hand; on the other, on the critics’ deployment of certain views of historical realities of gender relationship in the Elizabethan-Jacobean era. This paper explores in the interstices of the text and the historical context of the play. Instead of the unitary subject that most critics assumed in interpreting a dramatic character in terms of consistent motivation and action, I take up the notion of split subject that better explicates the inner conflicts of the character and expose the gap between her blurred motivation and ambiguous action. Seen in this light, Helena’s problematic character reveals itself as a desiring female subject that the patriarchal society will not allow to voice its subjectivity except in a properly “feminine” voice. Disallowed, and indeed disavowed, Helena ceases to seek a male authorization for her desire, and alternately turn towards a collective body of women for maternity as well as for matrimony. As recent historical scholarship has demonstrated, the gender relationship in the matrimony of the period ranged from strictly patriarchal to radically egalitarian. In this context the ‘end’ of All’s Well That Ends Well does not subscribe to total subversion or complete recuperation of patriarchal values; it signals the beginning of ‘problematic’ marriage life, in which both men and women have a lot to learn.