The story of Shakespeake in Love is about a poor playwrighter by the name of William Shakespeare. Shakepeake writes all of his playwrights to the owner of the Rose Theatre. After finding out that his former lover had been cheating on him, Shakespeare decides to put an end to his new comedy piece and changes the piece in a tale of tragedy known as Romeo and Juliet.
As time goes by, Shakespeake is unable to finish the play due to having writer's block, so he decides to hold auditions for the lead role, Romeo. A young man named Thomas Kent had left Shakespeare impressed with his audition. Thomas not only left Shakespeare speechless with his performance, but he was also a huge fan of Shakespeare's previous works. Shakespeake finds out later on that Thomas Kent is actually a young and beautiful woman named Viola de Lesseps who is a daughter to a wealthy merchant.
Soon after, Shakespeare and Viola become infactuated with each other and begin a secret affair. As this happens, Shakespeare begins to write about the story of Romeo and Juliet while being inspired by Viola's love and passion towards him. As this occurs, Shakespeare comes to the realization that their relationship is doomed. Shakespeake is married and Viola's parents have arranged for her betrothal to a poor aristocrat named Lord Wessex. Shakespeare then decides to disguise himself as a woman and pretends to be Viola's cousin and persuades Wessex to place a bet for 50 pounds if Romeo and Juliet will be a success story or not. If Romeo and Juliet is a success, then the money will go to Shakespeare himself.
Shakespeare decides to takes a different turn and replaces the lead role of Romeo to himself and a boy actor playing the part of Juliet. Unfotunately, the role of Juliet becomes replace as the boy actor's voice changes due to puberty. Viola replaces him and becomes the Juliet to Shakespeare's Romeo. The play becomes a success as the audience embraces the passion of both Shakespeare and Viola's performaces as the star-crossed lovers.