At the time the Plothole to the Isle of Sycorax opens:

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Duke Senior has been usurped by his brother, Duke Frederick; Duke Senior did not appear to put up much of a fight for his dukedom, but also fled to the Forest of Arden, where he lives like Robin Hood, with a loyal band of followers, including Lord Amiens, a jolly Entertainer who loves to sing, and Jaques, a much more melancholic and judgemental companion.

Following the recent death of Sir Rowland de Boys, his estate has passed to his eldest son, Oliver Charles. Although he was instructed to take good care of his younger brother, Orlando, Oliver Charles is instead cruel, denying Orlando the courtly training and education to be a gentleman. However, following his brother’s provocation, Orlando defeats Oliver Charles in a wrestling match, which is witnessed by Rosalind, a lady of the court; Orlando and Rosalind immediately fall in love, but Rosalind does not tell anyone about this except her best friend and cousin, Celia. After the wrestling match, Orlando is warned that Oliver Charles, now humiliated and vengeful, is plotting against his life, so Orlando flees to the Forest of Arden, where he joins Duke Senior’s pastoral court of lords living in exile among the trees.

Duke Frederick had until now allowed Duke Senior’s daughter, Rosalind, to stay at court, due to her inseparable friendship with his own daughter (her cousin), Celia. However, Duke Frederick suddenly banishes Rosalind from his court; she, too, decides to flee to the Forest of Arden. Celia, who cannot bear to be without Rosalind, goes with her, as does the court jester, Touchstone. To ensure the safety of their journey, Rosalind disguises herself as a young man and takes the name “Ganymede”, while Celia dresses as a common shepherdess and calls herself “Aliena”.

Duke Frederick is furious at his daughter’s disappearance. When he learns that the flight of his daughter Celia (disguised as Aliena) and niece Rosalind (disguised as Ganymede) coincides with the disappearance of Orlando, Duke Frederick orders Oliver Charles to lead the hunt for all three, threatening to confiscate Oliver Charles’ lands and property should he fail. Duke Frederick also decides it is time to destroy his brother Duke Senior once and for all and begins to raise an army.

In the Forest of Arden, Rosalind (disguised as Ganymede) and Celia (disguised as Aliena) encounter Silvius, a young shepherd pining for the love of a disdainful woman named Phoebe. When Rosalind (disguised as Ganymede) tries to intervene on behalf of Silvius, who is being continually rejected by Phoebe, instead, Phoebe falls hopelessly in love with Rosalind (disguised as Ganymede).

Soon after, they encounter Rosalind (disguised as Ganymede)’s beloved Orlando, who is equally lovesick. Taking her to be a young man, Orlando confides in Rosalind (disguised as Ganymede) that his affections are overpowering him, and Rosalind (disguised as Ganymede) declares that he is an expert in such matters and can “cure” Orlando of his lovesickness, if he agrees to pretend that “Ganymede” is Rosalind, and promises to come woo her every day. Orlando agrees, and the love lessons begin.

As Rosalind (disguised as Ganymede) tries to untangle the messy love quadrangle - intending to match Phoebe with Silvius, and to potentially end the charade with Orlando - Oliver Charles arrives, although he does not recognise Rosalind or Celia due to their disguises. However, although he believes her to be a simple shepherdess, Oliver Charles and Celia (disguised as Aliena) confess their sudden attraction and love for one another.