Reading Shakespeare is a lot like reading scriptures or anything that's written in a form we don't read everyday. If you do read it everyday, it's no big deal.
My mom's mother Betty used to say that if you wanted to learn about something, read a kid's book first. I think that's fabulous advice.
I realize that there may not be kid's versions of Shakespeare's plays but there are movies. With people you've heard of like Mel Gibson and Leonardo DiCaprio.
I think my favorite play is As You Like It. I've always wanted to play Rosalind. It's a little confusing with women posing as men and such but it's a great love story without a tragic ending. Read a synopsis, even a lengthy one before starting.
When I first started reading scriptures I would read a children's book about, say, Noah and the ark. When I read the scripture with phrasing that I wasn't used to, I could still follow the story because I knew what it was. That's maybe not the best example but you get the idea.
Well, now you all know I'm a total nerd about theater.
So, ya know, happy reading.