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I've been working with Ruby and Rails for over 2 years and I'm just about a month into learning Scala and Lift, so my opinion is probably biased, but here it is.
Ruby makes you feel amazing. Every new thing I discovered about the language made me giggle like a little schoolgirl. Working with gems is really simple and with Bundler and Gemfiles it is probably the best library management system I've came across.
There are loads of gems for everything, from API wrappers, to complex authentication/authorization.
Ruby also has amazing community that will make learning the language really really easy. Take RailsCasts by Ryan Bates for example. If you watch them, you will learn how to do web development with Ruby and Rails.
For me, Ruby is probably the best thing I've discovered in my whole programming life, because the way the community works made me change my whole approach to programming.
On the other hand, I don't see this in the Scala world. I don't want to raise a flame war, but this is just my impression after just starting to learn the language. In Ruby community, everything felt so engaging and made me wanna learn more and more. But with Scala, I tend to run into a lot of obstacles and not as much documentation and tutorials, that would help me overcome them.
There are tons of books devoted to very specific topis on Ruby, be it scripting, deployment, testing, and bunch of other stuff (yes Pragmatic Programmers rule). The best thing is, that the whole community f