East 9th near 2nd Ave because I mistook her for my then girlfriend, who I was meeting there. When she spun around in defensive shock and I saw who it was, I didn't help anything by saying "I'm sorry, I thought you were my girlfriend." This was in 2006 around peak Natalie Portman.
Best: Too many, but definitely includes the wedding of one of my closest friends in sunset, on a rooftop overlooking the West Village. And seeing fireworks on the East River from my balcony in 2018.