For the rest of the monkeypatching, i.e. add new methods, you could debug them really easy with something like this:

class Class
   def method_added(method_name)
      puts "#{method_name} added to #{self}, callstack:"
      puts caller.map{|line| "\t#{line}" }.join("\n")
   end
end

You can always add more code to filter by class or by method's name. Let's see an example:

$ more example.rb
require 'date'
require 'time'
 
class Class
   def method_added(method_name)
      return if %w(method_added).include? method_name.to_s
      puts "#{method_name} added to #{self}, callstack:"
      puts caller.map{|line| "\t#{line}" }.join("\n")
   end
end
 
class Time
   def to_date
      Date.ordinal self.year, self.yday
   end
end
 
class Date
   def to_time
      Time.parse self.to_s
   end
end
 
raise "to_date not working" unless
   Time.now.to_date == Date.today
raise "to time not working" unless
   Time.now.to_date.to_time == Date.today.to_time

The output will be:

$ ruby example.rb
to_date added to Time, callstack:
	example.rb:13
to_time added to Date, callstack:
	example.rb:19

Nice, isn't it?. Remember to be carefull with your monkeypatching, with great power comes great responsibility, it's just a tool, neither magic nor the panacea.