Using Ruby on Rails, I am constantly frustrated by things which might be nil, and having to construct such awful sequences as:

@order.try(:user).try(:name) || "anonymous"

Here’s an article explaning the origin of the debacle.

I call it my billion-dollar mistake…At that time, I was designing the first comprehensive type system for references in an object-oriented language. My goal was to ensure that all use of references should be absolutely safe, with checking performed automatically by the compiler. But I couldn’t resist the temptation to put in a null reference, simply because it was so easy to implement. This has led to innumerable errors, vulnerabilities, and system crashes, which have probably caused a billion dollars of pain and damage in the last forty years.
Tony Hoare, inventor of ALGOL W.