My first game programming language is Ruby and I'm still in love with it and hope to make something great with it someday. With that said, Ruby is very slow though. Unfortunately, there aren't many English game library/framework for ruby. However, Japanese people are pretty active with Ruby game development. Here are the libraries I've found so far
Gosu - Tried it, and love it. Very easy to use, very powerful ( for ruby ). The only thing I don't like is the Audio library. It use FMOD on Windows, so you can't make a commercial game without paying for a licesne fee to FMOD.
Ruby/SDL - It's basically a port of SDL to ruby. It's pretty good and if you want something low level, then this might be a great choice.
On the Japanese side we have..
Miyako - Very active ruby library. It can play video file and do lots of things. They even come with a Visual Novel framework. It actually wraps Ruby/SDL so that you can use them easier.
http://www.twin.ne.jp/~cyross/Miyako/MyGame - This one even has a book in Japanese, so it's pretty good. A pseudo-3D racing doujinsoft has been made using this library. I tried it and it was ok. Like Miyako, this one also a wrapper for Ruby/SDL.
http://dgames.jp/ja/projects/mygame/DXRuby - This one is what I really like. Unlike the other two libraries, DXRuby wraps DirectX and it's pretty fast for a ruby. It comes with collision detection system as well as extensions like sprites and animation, which all of them are written in C so it's pretty fast for Ruby.
http://dxruby.sourceforge.jp/I tried to wrote a game engine/framework that use Ruby too, But didn't have time to finish it
http://rubix.gptouch.com/home Maybe one day... maybe...
Anyway, my experience with Ruby has been good so far. Like people here have said, I don't have much problem with the syntax at all. And even if I do, many of them can be solved easily. Code is easy to read too, due to the nature of the language. The only problem I have is it's hard to find good IDE. I used EasyEclipse with Ruby plugin before, but since the game I made has to use Japanese language and the IDE didn't seems to support it so I have to drop that. If you have no need to use non-English language, then EasyEclipse should be the one to go with. Another one is Aptana IDE, but it crashes on me quite often and eats my memory everytime I run so I don't know what's up with that. I ended up using Notepad++ to code the game in the end lol.
As for packaging the game, I'm not sure about other OS but for Window you have ruby2exe, exerb for Ruby 1.8.x and OCRA for Ruby 1.9. Oh, that reminds me. One thing you should think about is which version of Ruby you want to go with. Many libraries support only one and not both. I used Ruby 1.9 for better encoding support, since I have to use non-English language in my game.
Ughh, sorry for the long post. But it isn't often to see Ruby being discussed around here so I got a bit carried away...