Really depends on what you mean by "simple". "Simple" is one of those descriptors that gets tossed around a lot in programming by rarely with a clear definition

Really depends on what you mean by "simple". "Simple" is one of those descriptors that gets tossed around a lot in programming by rarely with a clear definition. Python is a "simpler" language with its preference for "one obvious way", and it does tend to support fewer paradigms than Ruby. Ruby is a more complex language, supporting many approaches. But if you are familiar with the various approaches, that can be "simpler" if it allows you to choose the most fitting approach for whatever problem you have at hand. To put it another way, "simple" can mean "the language is small/has an obvious way it wants you to do things", or "simple" can mean "the language is flexible enough to be used to model your problem in the most appropriate way". Python is the first kind of simple, Ruby is the second. IMHO Ruby is much more expressive than Python, and the stdlib is better designed and less crufty. Ruby really has one of the best stdlibs around, I think, and a lot of languages could learn a lot from it - particularly the design of `Enumerable`. So I prefer Ruby when I have the choice. Part of that is probably just familiarity, but I've been a full time dev on both Ruby & Python projects for long stretches of time so I think I'm in a decent position to compare them. My personal preferences/taste is another aspect, of course, and there's no objective accounting for that. The case where I often will prefer Python is if I'm scripting something that needs some degree of portability. If you pick a random Linux box it's much more likely to have some version of Python installed than Ruby, so if I'm writing something that should be easy to copy to a box and use without additional setup, I'm more likely to pick Python.