Perhaps no play of Shakespeare's is more directly connected to his personal life than Twelfth Night. While it is always dangerous to make ringing assertions about the correlations between Shakespeare the person and Shakespeare the writer, it is hard to deny that such correlations exist in this play.
Shakespeare's twins, Hamnet and Judith, were born in 1585. Hamnet, who was Shakespeare's only son, died in 1596 at the age of eleven. Twelfth Night, a play about twins separated in a shipwreck, may have been written as little as three years after Hamnet's death. It could not have been later than 1602, the date of the first recorded performance. Gary O'Connor points out the connections: "In Hamlet Shakespeare had brought back to life his lost son, Hamnet. In Twelfth Night, in his concealed allegorical manner, he broached again in glittering terms the subject of his own twins, concentrating almost wholly on the girl and boy bond. . . . Viola stands in for them both, playing her brother as well as herself. . . . In such a way, since Hamnet's death, had Judith stood in for Hamnet" (William Shakespeare: A Popular Life [New York: Applause Books, 2000], 204).
There are, of course, two women who have lost brothers in Twelfth Night, one permanently and one temporarily. Olivia's grief for her brother's death is obvious, even ostentatious. Valentine reports to Orsino that "to season a brother's dead love" Olivia "like a cloistress . . . will veiled walk" for seven years. (All references to act, scene, and line numbers in the play are to Bruce R. Smith, ed., Twelfth Night: Texts and Contexts [New York: Bedford/St. Martin, 2001], 1.1. 27 30). She has removed herself from society and from male-female relationships, and her mourning clothes are the outward sign of her withdrawal. Viola's grief is much less obvious, but she pursues the same purposes. When she disguises herself as her brother, she is partly trying to fill the void caused by his absence. In the process, she has removed herself from male-female relationships even more effectively than Olivia has done. Her male disguise may not look like mourning clothes, but it removes her from the possibilities of courtship and demonstrates a grief so great that Viola has eliminated her own identity in order to keep a semblance of her brother alive. Viola is caught between two worlds, two states of being, created by the great bond that she feels for her twin brother and the confusion and consternation of his possible death. When Orsino asks, "But died thy sister of her love, my boy?" Viola/Cesario answers, "I am all the daughters of my father's house, / And all the brothers too—and yet I know not" (2.4.116 118). It is not entirely clear who is alive and who is dead, almost as though both must live or both must die.
Viola and Olivia's first meeting is enormously important. When the two of them meet face to face, they find their disguises distinctly uncomfortable. Olivia quickly realizes that a seven-year period of mourning is no longer a reasonable goal. In fact, she is willing to abandon her grief for her brother and replace it with love for Cesario. Viola/Cesario, who has previously announced her desire to marry Orsino, now experiences the passions of jealousy (of a rival) and envy (of that rival's beauty). The point of transition for both of them, the symbolic instant, is when Viola asks Olivia to draw back her veil and Olivia does so. Olivia has at least temporarily removed the physical barrier or mask of grief that keeps her from seeing the world and being seen by it. Olivia's love for Cesario then forces Viola to the realization that she cannot maintain her mask of grief, her impersonation of her brother, indefinitely.
Ironically, this confrontation between romantic rivals will ultimately free both of them to pursue the loving relationships they really want. Olivia announces her conversion from lady in mourning to lady in love with the words, "Even so quickly may one catch the plague?" (1.5.240). For Viola, things are a bit more complicated, but she has also come to a realization. She says, "Disguise I see thou art a wickedness." She then goes on to make clear just what a mess she is in, "What will become of this? As I am man, / My state is desperate for my Master's love; / As I am woman—now alas the day!— / What thriftless sighs shall poor Olivia breathe! / O Time, thou must untangle this, not I; / It is too hard a knot for me t'untie!"(2.2.30 35).
For Olivia and Viola, the loss of a brother creates a void and a need for that void to be filled. For both of them, love comes as a solace for grief and as a promise of future happiness to replace past pain. In Twelfth Night, Time does untangle the knots. Sebastian, Viola's brother, returns, Olivia can marry the man she loves, and Viola can marry Orsino. It is an almost fairy tale ending for the married or about-to-be-married couples, a happily ever after conclusion that seems to banish all sadness. However, in the play as in Shakespeare's real life, there has been a death. Olivia's brother will not return, nor will Shakespeare's son.
Perhaps one of the most important messages of Twelfth Night is that Time does heal, grief is not the end, and happy endings are possible.