I have no idea why this works

your code is definitely wrong. if you golf a bit less then you'll have room to insert print calls to find out what happens.

maybe the test output is confusing though.

Am I missing something with the Python random tests?
System says these should all return True, but I'm returning False:
big bad by her thing work it child other come
get new try have I large see her as it will
there an come on number call
tell 3.15 take all high child their time life thing call
high same to ask group find life over year they 3.15

This seems like the system has a few of the answers incorrect.

I enjoyed it, but if anything nessie would be mesolithic not paleolithic. And yes I am that pedantic.:)

That's a problem with your code, not a kata issue.