Here's a good one; a
group of fifth graders were going on a field trip from Colorado to DC and Philadelphia. The parents were assured that while it would be four kids to a room and two kids to a bed, boys would be kept on one floor and girls on the other.
Well you can probably see the loophole there:
Apparently he was supposed to be in "stealth mode," but couldn't resist sharing his secret identity:
It is unmentioned as to whether the different female student was aware she was going to be sleeping with a boy, although this makes me suspect not (from the complaint):