Ruby's object system is much nicer than Python's, but Ruby has plenty of warts of its own. For example: extremely complex syntax compared to Python's LL(1), overloaded constructs like blocks/procs/lambdas (whereas Python just has functions), and cryptic Perl-isms ($_ etc).
Another example, initial setup is beginner-unfriendly. No IDLE-like barebones editor provided out-of-the-box in the standard install, just the REPL. Anything beyond that you must figure out and configure by yourself.
Most rubists like the optional parenthesis, but I suspect must devs don't.