There is great stuff to say Ruby and RoR. But I have yet not experienced the "smile" that DHH is describing. Especially when I have to read and understand the code written by colleagues (or myself mind you).
To do my job I had first to become a master in grep to find where stuff come from and deciphering half assed documentation. Mostly because exploring objects with hundreds of methods is not my cup of tea.
I also enjoy understanding my tools, and RoR is, in my experience, not particularly easy to understand. This doesn't put a smile on my face.
batiste, I think what you are describing is that the culture around Ruby doesn't put a smile on your face, rather than just Rails.
Ruby's philosophy is quite a bit different from Python, Smalltalk, Perl, Java, and PHP. Ruby is roughly described as "batteries included." Some people don't prefer this, as it encourages meta-programming and introspection rather than explicit instructions.
A lot of libraries and tools around Ruby use meta-magic; some libraries have been attempting to strike a middle ground with meta magic, such as Datamapper (explicit) vs ActiveRecord (implicit). But the bias is definitely towards implicit; or as what DHH calls "omakase."
Lots of people don't like maintaining other or former colleagues' code, especially when the codebase starts turning into a legacy one. This is true in every language.
There are several solutions for this, but I personally take the easy way out: quit your job and be the first developer in a new startup, or do some freelance work. Whatever you need that floats your boat