Ruby does a lot of magic stuff to help beginners. That means the semantics are unclear. IMO this is similar to how Apple optimizes UI/UX for first impressions to drive sales. The journeyman user is neglected, simple things are easy to do, but the most powerful features are missing for journeyman and advanced users.
I'm not saying Ruby is a bad language. Just saying that I have the opposite view. I too love to learn, but Ruby did not help me learn, it actively got in my way.
You can make a simple language without confusing semantics, see Go, C, python.