They are surprisingly different. Ruby has a focus on developer joy and productivity. In some cases this comes to the detriment of language simplicity, and exis

They are surprisingly different. Ruby has a focus on developer joy and productivity. In some cases this comes to the detriment of language simplicity, and existing features can complicate language evolution. Surprisingly with this complexity Ruby has had a bit more success with optimized implementations than Python, such as Truffle Ruby. Ruby is a bit more multi-paradigm than Python IMHO, and has been jokingly called a "language for connecting adults". One can monkey-patch override division to return fractions, with the person maintaining the project deciding if this is a good idea or not. This can potentially make projects with a large number of dependencies harder to debug, which interestingly seems to have created some push-back on importing lots of arbitrary dependencies. With both Python and Ruby, you wind up having divisions between dependencies because of the poor mismatch between different paradigms - for instance, libraries built to work with Python Twisted or Ruby EventMachine for I/O, or libraries built to work generically or to integrate into say Django on Python's side or Rails on Ruby's side. Interestingly the communities seem to have different key focus areas - Ruby has historically been very focused on testing (cucumber and selenium for instance) while Python has had a lot of focus on documentation (pydoc and sphinx). Oddly, neither really has had a noticeable literate programming push.