I'll also add it depends on your what OS you're running. If you're on Windows, Python will be more forgiving than Ruby. Some Ruby gems build native extensions

I'll also add it depends on your what OS you're running. If you're on Windows, Python will be more forgiving than Ruby. Some Ruby gems build native extensions as they're installed, which isn't always possible on Windows. Granted, the state of Ruby and Rails on Windows has improved over the last few years, I still wouldn't consider it a first class citizen. Granted, there are some nice online resources for jumping into Rails: http://www.codeschool.com/ http://www.codeschool.com/ http://tryruby.org/ http://tryruby.org/ http://rubykoans.com/ http://rubykoans.com/ http://mislav.uniqpath.com/poignant-guide/ http://mislav.uniqpath.com/poignant-guide/ http://humblelittlerubybook.com/ http://humblelittlerubybook.com/