How old is that? I'm over 50 and I still can't get into Shakespeare. Watching a performance is OK, though not something I'd choose to do on my own, but reading the plays? Can't get into it at all.

Have you tried an annotated one? Shakespeare is full of, essentially, in-jokes and memes from the 1500s. There is a ton of depth in his writing that you'll totally miss if you don't know all of that context.

Also, lots of bawdy humor that gets glossed over by staid and respectable modern productions. For example: the "bite your thumb" gesture that gets used in a few plays is pretty much the equivalent of somebody from today giving a double middle finger while sticking their tongue out.

Try watching a movie version - I really like Branagh's Hamlet and I never expected to (long though)

Try the "Sonetts" instead of the plays!

Just program.