I chose Ruby mainly because of all the syntactic tricks and weirdness but despite slowness. You might choose Python for exactly the same reason; e.g., I wouldn

I chose Ruby mainly because of all the syntactic tricks and weirdness but despite slowness. You might choose Python for exactly the same reason; e.g., I wouldn't use Ruby on teams with >2 developers, especially in Google. Python is more straightforward but at a (small) price of freedom. Example: you can rapidly prototype in Ruby using blocks and extend basic classes (even integer) using monkeypatching. I was fascinated by this, yet I wouldn't monkeypatch when working with other people so that advantage goes out of the window.