He’s not being the Nice Guy, imo. He’s the asshole telling you to smile as you walk down the street. Where the hell do you get off telling other people how they should feel about getting hit on? How is it any of your goddamned business?
Furthermore, your hypothetical is broken, because you’re trying to dictate the woman’s initial reaction to the guy hitting on her. Why would you think it remotely useful to dictate that my reaction to ugly guy and attractive guy is exactly the same? If my reaction were the same to both, then I’d feel the same way about both, which I obviously don’t. So, by dictating my reaction, you’re also dictating how hypothetical me feels about the guys. So, I suppose, in your perfect situation, I’d react to persistence exactly the same way with both guys, as the parameters of your hypothetical have dictated my reaction, and, by extension, forced hypothetical me to feel the same way about them, so if I find the ugly dude creepy later, I have to have pulled a switcheroo on my emotions and started finding the guy creepy out of nowhere, so you have support for your thesis that I’m not really turning him down in a way he’d understand.
And you don’t find this to be completely obnoxious at all?