I started a new contracting gig a couple of months ago, in Ruby. I had used it briefly years before in another project, but it was so long ago that I had to learn it again basically from scratch.
Although I don't really think the language is anything special (i.e. it's a standard dynamic OO language), what really turns me off Ruby is this dogmatic, almost religious aspect of its community.
Take POODR - it's more or less the community bible. If it's not written in POODR - don't do it. If it is - do it that way or else. It's POODR's way or the highway.
According to more experienced Rubyists more than 80% of the Ruby community use Rails. Rails is so widely spread that its development even fundamentally affects Ruby's roadmap.
Now irregardless of what you think about POODR or OO or dynamic types or whatever, a homogenous echo chamber filled with people chanting the same things over and over again is not a good thing.
As a counter example, take Javascript. Yes, it has its warts; its equality table is a joke. Ruby is a better thought out and implemented language in almost every aspect (although I do like Javascript's minimalism better, but that's a matter of taste I guess.) However, Javascript's community is as diverse, vibrant and experiment-friendly as it gets - there are the OO diehards, but there's also React, fantasy-land, macros, monads. People are trying out new things constantly.
Now I know you have monads in Ruby too or flow-like gradual typing libraries or rewrites of Clojure's spec. But at least where I work (and I work with some very experienced Ruby people) those libraries and the ideas they embody would never ever be considered as serious alternatives for anything. POODR or else.