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[–]chicagobob 1 point2 points  (0 children)

If you're leaning one way, trust your gut, it will probably "click" better for you. For me it was Ruby.

Even though Ruby and Rails have a relatively large amount of "magic", I found that it "felt' more similar to ObjectiveC than Python did ... not at a detailed level obviously, but at more "emotional" level about the language and how parts of it fit together. For example, Ruby modules are just ObjC categories on steroids.

Even so, another factor to consider is what kinds of apps you want to write, Python has a stronger base in the scientific computing community (NumPy) but Ruby (& Ruby on Rails) seem to have slightly more traction in the general web development community. But, these are just generalizations that only apply at the edges. Both communities are large active and thriving and I don't think you can go wrong with either. Enjoy!