A subjective rant: I tried to get into Python about 5 years ago - worked through 'Dive Into Python' and used it for several projects.

Once I tried Ruby for a few projects, I never looked back: I now only use Python when I need a library that is only available for Python.

So, try both for a few small projects and take your pick.

BTW, I think that being proficient in just one scripting language is enough. I split my work time between Ruby, Common Lisp, and Java - perhaps not an optimum choice, but flexible enough for most problems that I need to solve.