I've been using Ruby for the last 10 years, and sometimes I don't realize how normal a method/class or a way to do things are for me.
I really like Ruby, it is a great language. But how can I help someone to start studying it? Or even better: using it.
Get to know the very basic of the language. Start reading Ruby Tutorial, I like the “learn you for Great Good” series, and this Ruby Tutorial is very similar to it.
Then, my controversial suggestion, start writing code using Ruby on Rails.
I suggest creating a Ruby on Rails app just because it is something useful. The first app that I created was an app to track hardware status (purchased, broken, fixed) and which sector of the company that hardware was. I must have created it 5 times before I got one that I really enjoyed :).