I'm definitely a Python person, having used both fairly significantly - Python about ~12y, Ruby ~3y. One thing I think Ruby gets right is the naming convention

I'm definitely a Python person, having used both fairly significantly - Python about ~12y, Ruby ~3y. One thing I think Ruby gets right is the naming convention for methods that modify the object they're called on (<obj>.<method>!) and callables in general that return a boolean (<callable>?). My biggest gripe with Ruby is the class implementation. I find metaclasses a bit more difficult to understand in Ruby. I hate that I can't easy determine where a given method of an arbitrary object is defined. I recall that it wasn't uncommon for popular libraries to "open up" a class that was an integral part of Rails and redefine methods, overriding the original implementation. I recall trying to figure out why the method I was calling wasn't returning the value I expected, even after reading the Rails source. Come to find out, some random library had overridden it. They'd matched the behavior of a previous Rails version, but the Rails behavior had since changed. I spent hours on that specific problem and still resent it to this day :P.