A younger person whom I know offline recently complained to me that she doesn't like to read Shakespeare because the plays are “boring and difficult to understand”. She wanted to know if I had any advice.
I did, and I do. These tips may help some of my readers who are also struggling with Shakespeare.
1.) Remember that the plays were meant to be performed, not read. Shakespeare never intended for his plays to be read like the latest James Patterson novel. In many public libraries, you can borrow recordings of the plays, performed by professional stage actors. Since each role is played by a different person, this format really brings the play alive. (I also recommend attending live performances, of course; but this will not be practical for everyone.)
2.) Start with the most accessible, popular plays. In other words, don’t make Timon of Athens the first Shakespeare play you read. Start with the best known ones: Macbeth, Romeo and Juliet, Hamlet, Julius Caesar, King Lear.
You will also find extensive commentaries and summaries of the most popular plays—much of it available online.
3.) Buy an annotated edition. Shakespeare’s works are in the public domain. This means that there are many competing editions. But some editions are better than others.
You should buy an edition that has annotations—or sidebar explanations—of the many unfamiliar words and historical/cultural references that you’ll find in any of Shakespeare’s plays.