I've known about Ruby for a while, and picked up on the hype, mostly because of the Ruby on Rails framework. I started learning Ruby just a few weeks ago at work, courtesy of our architect looking to stretch the development team's repertoire. It wasn't hard to learn, and the fact that the built-in libraries are clearly not as extensive as in Java (of course) - it wasn't really much of a hurdle, as most programmers probably use only a fraction of what's in the JDK. The fact that it has multiple method names for doing the same thing (Array has size() and length() - WTF?) also wasn't that much of a deterrent. In contrast, I've been planning to learn Python for the past few years, but never seem to have gotten over the completely useless self parameter in its constructors. I like what I've seen so far in Ruby, the integration of regular expressions in the language, meta-programming and the whole "domain specific languages" aspect, and Ruby gems - almost all good so far. At one point I was wondering why I didn't give it a go much earlier.
Then I remembered the biggest thing that turned me off: "Why's Poignant Guide to Ruby". I have never seen a more self-indulgent, verbose, time-wasting programming language tutorial. The first time I came across it I was completely put off by the cutesy cartoons, the "trying hard but not good enough" humour, and the irritating and annoying asides and stories. I think I got through a chapter or two and gave up in exasperation. I was clearly not the audience this dude was writing for. He was possibly writing for children - "oh yes, the array is like a biiiig caterpillar, and the commas are its legs!", or teens with ADHD who needed frequent distractions to keep them reading the text (yes, I don't know how that's supposed to work).
I'm going through it again, this time as someone who doesn't actually have to learn from his text, and while I appreciate some of the things he seems to be reaching for, the abstractions he's trying to convey, I still think it takes up too much time to get to the point. It just smells too much of condescending "edutainment". If you ever wanted to read a document that treats you like an idiot - waay more than those "For Dummies" or "Idiot's Guide" books - this is it.
And yes, I know there are a lot of other excellent Ruby tutorials out there, but at the time I first encountered the Poignant Guide, I didn't actually have any use for Ruby at my then-workplace, so my exploration never went any further.