For one of my sites, I need to check if several class attributes are defined and not empty. So far, I've happily used if self.attr:, which in my mind is the shorthand for if self.attr is not None and self.attr is not '':, or whatever the undefined value of the attribute is.
This works fine, but yields to surprising behavior when checking multiple string attributes. '' and '' is not False (as I expected), but ''. 
This begs the question: are there other types for which the and operator does not force a typecast to bool? 
I can't come up with an example where this difference in behavior would cause an actual different outcome for the if-clause (after all, '' still evaluates to False), but am left with the gut feeling that there's edge cases that could be a trap.
Lastly, I'd be keen to know if anybody knows why it was implemented that way? I thought the Zen of Python encourages one way and one way only, and the + operator already seems to bethe intuitive way for string concatenation.