I gave a talk on Python idiosyncrasies a while back that you might enjoy:

https://speakerdeck.com/alangpierce/python-puzzlers

Several of the examples from that talk have equivalents in JavaScript where JavaScript does better. I think pretty much any real-world language has lots of surprises like this that you need to get used to, although I certainly admit JavaScript (particularly JS type coercion) tends to have especially surprising behavior.