Since C# ties you to a single OS,
That is no longer the case with Mono, but that is a whole different monster for another thread.
Core Ruby programming is not necessarily intended for Web development. However, Ruby has been extended into some Web development frameworks, the most common being "Ruby on Rails," followed by Rack and Sinatra among others. It's debated if one should know Ruby before using Rails, etc, but I feel that depends on the user and how steep a learning curve they can handle. Conventional wisdom should dictate that at least a
basic understanding of core Ruby should be attained before tackling rails, etc. "rails tutorial" by Michael Hartl, is a pretty good (and free!) book online that walks you through setting up a Rails development environment to using git to running you rails app in the cloud.
Ulf mentioned Python, which is (IMHO) is another good language to have in your arsenal. One of the beauties of Python is that it plays nicely with other languages and there are many libraries available and Python Web frameworks as well. I think Henry's post is probably the best advice in this thread. I recommend looking at some of the "MOOC" courses out there offered by many universities. You do not have to participate in the course, but you can see what text book was used and probably get instructor notes as well. This may help you gain an understanding of the topics Henry suggested.
Steve