Everyone has an individual background. Someone may come from Python, someone else may come from Perl, and they may be surprised by different aspects of the language. Then they come up to me and say, 'I was surprised by this feature of the language, so Ruby violates the principle of least surprise.' Wait. Wait. The principle of least surprise is not for you only. The principle of least surprise means principle of least my surprise. And it means the principle of least surprise after you learn Ruby very well. For example, I was a C++ programmer before I started designing Ruby. I programmed in C++ exclusively for two or three years. And after two years of C++ programming, it still surprises me.

Yukihiro Matsumoto "The Philosophy of Ruby, A Conversation with Yukihiro Matsumoto, Part I" by Bill Venners on 2003-09-29, Artima Developer