Yes if doing this to art work you are making a lot of work for yourself. You can simplify this process, before you Make Path, go to Edit > Select by > Open Objects; this will select all of your single cut lines, go to Arrange > Make Path. Go back to Edit > Invert Selection, this should select all your fully defined male and female parts, go to Arrange > Make Path and create your Male Tool Path. Click on one of the single cut lines and this should select them all, create Online Tool Path. Go to Layout > Sequence by List and set your online tool path to the top of the list. Alternatively you could select your male tool path and go to Arrange > Order > Send to Front, whatever is set to front will cut out last.