An early classic, from the guy who brought you "check out sex tape."
Now, it's just good foresight to discuss sexual health with prospective partners and exchange the requisite paperwork, and we would never shame someone for practicing safe sex. But this wasn't a discussion our future national embarrassment was proposing -- he insisted that his dates be tested by his personal doctor before he so much as made a reservation. There's conscientiousness and then there's scary control freaking, because believing that any woman willing to date Trump is smart enough to forge a doctor's note is a bit generous, to say the least.
Reminder that Trump's doctor since 1980 is this guy.
It's worth noting that at the best of times, Trump sounds like a Mad Libs filled out by a robot that has gained sentience and gone insane, and he wasn't any better back then. To explain his demands, he said, "It's one way to be careful. There are a lot of ways. I'm saying, take all of those ways and double them, because you will need them. It's very scary out there." As if there's some shadowy cabal of New York supermodels hunting him down and trying to give him the AIDS ... perhaps even as we speak? Tragic foreshadowing.