I haven't really looked at Ruby that hard, but from my perspective as a reformed Perl user I found Python's syntax to be very clean and well organized. On the surface ruby looks more Perl-like to me, more clutter, not as easy to read as Python.
Having found Python, I really don't feel a pressing need to learn another scripting language. Instead I'm working on Objective C.
Part of what makes the difference is cultural. It is of course possible to write very legible Perl code, but that was, at least for a time, far less visible than the "cool hack in 1 line of extremely dense code" culture, and all the "more than one way to do it!" stuff. Ruby can be messy, but there is a tendency to keep a lid on it.
I totally agree about picking the languages you want to learn. There's only so many hours in the day, and you will have different pref's on style and language design, anyway.
I'd love to learn Scala (after being a Haskell and Ruby fan for years) but finding the time is incredibly difficult...
Having found Python, I really don't feel a pressing need to learn another scripting language. Instead I'm working on Objective C.