I find Python easier to get started with, because there is much less syntax to learn when coming from another language, particularly the ones you have been working with. Ruby does more out of the box for webapps, and does more with less characters, but only marginally, and it has a slight perl aftertaste that makes it a tad annoying at times when you're starting. In summary, I'd recommend you start with Python because you can learn essentially all of the language in very little time from the basis you already have. Ruby is definitely more hyped right now than Python, and it is awesome for web stuff, but starting with Python and then learning Ruby should be easier than the other way around. Or maybe it's just so for me.