The language isn't typeless. Other language (python and ruby, among many others) manage to integer and string comparision correct.

It is trickier when someone compares "2" and 3, should we say it's invalid (my preference) or turn 2 into an integer, or 3 into a string? However, there is NO reason for there to be an issue comparing 1 and 11. This is just an unfortunately mistake that is too deeply baked into the language to fix at this point.