A wise man once yelled at me after I badgered him with questions one too many times, "Use the source Luke". And that's what I'd recommend. Read as much Ruby source code as you can (ahem, github), make the effort to understand why the authors designed a piece of code the way the did. The Rails source continues to evolve into a great example of interesting to read Ruby - but you might want to start out with something a bit simpler like Sinatra :)