Python's "there should be 1 obvious solution to any problem" culture is way better at scale than Ruby's "there should be 5 subtly different solutions to every problem". I hate the distinction between blocks, procs, and lambdas. Ruby's support for both `...` and `..` likewise does more harm than good. That extra period can be easy to miss while scanning code and we all know how much more important readability is than writability. I also don't like the difficulty to distinguish "magic" references from real ones, unlike in Python where all the magic references have double underscores. It once took me a half hour just to figure out why this seemingly normal method called `method_missing` was being invoked when it seemed like it shouldn't (this codebase was so large and classes had so many ancestors / mixins that finding method definitions was generally a problem. I also don't like mixins btw, or inheritance for that matter, but having 1 is better than having both).
I would discourage anybody from learning Ruby for the simple reason that large Ruby codebases are a scourge to our profession. Small Ruby codebases may be fine, and large Python codebases aren't great either, but I much prefer the language that minimizes all the weird gotchas.