It is notable that you said "Writing Ruby feels..." but made no mention of _reading_ Ruby. I think I agree with you that I enjoy writing Ruby more, but I definitely enjoy reading Python.

It's definitely easy to write unreadable Python code, just as your can write easily readable Ruby code. But I think that some of the "clever" things that the Ruby language allows (some of the things that make it fun, things that aren't considered obscure or advanced features) tend to make Ruby code more difficult to comprehend.