Ola Bini manages to express my feelings about the difference between Ruby and Python:

So what’s the point? Well, the point is Ruby. In fact, Ruby has almost all of the flexibility of Perl to do things in different ways. But at the end of the day, none of the Perl problems tend to show up. Why is this? And why do I feel so comfortable in Ruby’s “There is more than one way to do it” philosophy, while the Perl one scares me?

I think it comes down to language design. The Python approach is impossible for the simple reason that what the language designer chooses is going to be the “one way”, by fiat. Some people will agree, and some will not. But what I’m seeing in Ruby is that the many ways have been transformed into idioms and guidelines. There are no hard rules, but the community have evolutionary evolved idioms that work and found out many of the ways that doesn’t work. This seems to be the right way - if you do the choice as a language designer, you have actually chosen the people that will use your language: that’s going to be the persons who doesn’t dislike the language designers choices. But if you leave it open enough for evolutionary community design to happen you can actually get the best of both world: both a best way to do things, and something that works for a much larger percentage of the programmer world.

– http://ola-bini.blogspot.com/2008/02/language-design-philosophy-more-than.html

I like constraints, they can be liberating, but I also want to be treated as a grownup when it comes to breaking them. So Ruby’s socially suggested guidelines are much more comfortable to work with than Python’s enforced style.