As a writer and a reader, the most interesting stories are often where the lead character is a situation that he or she has never been in and must figure out a way to survive.
Adding the element of the lead character dressing as the opposite sex to the stranger in a strange land story and we have William Shakespeare’s Twelfth Night or What You Will.
In 1996, a film adaptation of the play was released.
Viola (Imogen Stubbs) and Sebastian (Steven Mackintosh) are twins. They are traveling on a ship that is torn apart during a storm. Believing that her brother is dead, Viola dresses in her brother’s clothes and takes on the identity of Cesario. Viola/Cesario becomes the adviser and confidant to Orsino (Toby Stephens). Orsino is head over heels in love with Olivia (Helena Bonham Carter), but Olivia is in mourning for her brother and is using the mourning period to keep Orsino at arms length. Viola/Cesario is sent in Orsino’s stead as a messenger. Olivia falls in love with Viola/Cesario, not knowing that he is actually a she and she is in love with Orsino.
The best romantic comedies come from misunderstandings. This play and this movie is full of misunderstandings. Especially when there is cross dressing involved.
I recommend it.
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Writergurlny 
Twelfth Night is my favorite Shakespearean comedy.
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