I think one of the arguments for Ruby over Python is the whole Theres More Than One Right Way To Do It philosophy which does make things significantly easier to write down in Ruby, especially coming from scratch. This is much like Postel's principle---a computer should be receptive to many slightly malformed inputs because they will happen. That makes the computer more successful.

The problem is that once you start accepting malformed inputs you can never be rid of them and thus you have a permanent tower of babble[1] problem.

[1] intentional