I've used both. I actually think that Ruby is a nicer language in most respects than Python (except for way too many ways of expressing the same thing in syntax), but Python is a much better 'platform'.

Python struck me as somewhat clunky at first, but after working in it for a few months, I didn't really have any issues with the language. I think there will always be initial resistance for anyone using a different language, but I don't think your mind is necessarily set to where one language will fit it and one won't. Imperative programmers moving over to functional languages will find that functional languages don't "fit their mind", but given enough work in one will probably find that their mind changes to where functional aspects make perfect sense.

So I think that's the case with Python. Some people won't find it clunky at all, for those that do, working in it for some time will probably lead to their mind fitting the language better. Personally I'd rather do that than deal with the issues Ruby the platform has.

Anyway, Ruby and Python are a lot more alike than different.