OP This happened to me five times (over 25 or 26 years).
#1 Mid-90s AOL hookup. I was drunk and sloppy and I wouldn't have hooked up with me either. I took a cab about 15 blocks from my place to his on the upper east side. It was very late at night and neither one of us had phones. He said he would be walking his dog and would look for me getting out of a cab. I did. I saw him, he saw me, and I walked (stumbled?) toward him. He did not acknowledge me and let himself back into his building.
#2 and #3 Later than #1, but pre-9/11 and via Gaydar or Manhunt or BigMuscle.
#2 I took a cab to his ghetto block on the LES. It was a hot and disgustingly humid night and his sidewalk had a garbage bag with one of those nasty antifreeze-looking ooze puddles in front of his building. I cannot remember if he came down to meet me or if I went up to his apartment, but he checked me out and said, "I'm sorry. This is not going to work for me." He was a ginger with a sleazy vibe and I remember thinking, before he spoke, "I could just leave," but decided to just enjoy myself with him. When I left, I was more annoyed that I had taken two cabs with no payoff.
#3 This was more like he wanted a date/I wanted a hook up. He worked in theatre and took me to a show he had free tickets for. I felt him staring at me all during the second act as if he were deciding "should I or shouldn't I?" Again, I would have hooked up with him even thought he misrepresented himself in various ways, such as saying he was 6 feet tall and was clearly 5'9". He gave me mixed signals all night and we went for a drink after. He said to me at least three times "I hope you find what you're looking for." Very syrupy and fake.
#4 Cut to maybe 2009? By this time, Grindr had been launched, I had found my sexual self and my assertiveness, and I looked great. I had been with a lot of men via Grindr and I never rejected anyone in person and always made the best of it. I would just ghost them afterwards if they contacted me, with the exception of 3 or 4 guys I saw a few more times each. But one guy (#4) had me come up to his (nice, midtown east) apartment. We sat on his couch in his (too) brightly lit living room and I was ready to pounce. I had a massive hard on and put his hand on my jeans. He said, "Very nice. Feels big." Then he took his hand away and said and did nothing. After a few more awkward minutes I realized this guy did not know how to reject me so I left.
#5 Weirdest non-hookup, hookup I ever had: I had been chatting with a guy on Manhunt for maybe a year or even two. He was an amazing looking, handsome, muscular bottom. Definitely had masculinity issues, was very into "straight-acting." He was on a business trip to NYC and was staying in one of those hotels on Lexington in midtown, maybe the W. He had to come down to the lobby to meet me and take me up to his room because the elevator had a keycard system. Very handsome and built in person, of course shorter then he said but I did not care. Got to his room and he got naked quickly and got on his bed, supine. Then, he said nothing and did nothing. I touched his body. Tweaked his nipples. Nothing. I got my very hard dick out and slapped it on his pecs a bit. Put it near his face. No expression change. Motionless. It was like this guy was this beautiful sex-robot but his battery was uncharged. His cock was soft and stayed soft. I know I asked him once or twice, "What do you like? What do you want me to do?" Maybe he shrugged but he gave me nothing. So after a few more minutes, I said something like, "OK, maybe we'll try for this another time." I let myself out. He contacted me a few more times over the next year on Manhunt but he never made any indication that we had me before and I just ignored him. Weird dude.