For me, the craziest way I met a man was many, many years ago, here in Toronto at the old Woodbine Racetrack, (now long gone). I had gone there with some straight friends from work, and since I didn't know jackshit about horses, and didn't gamble, was expecting a night of being totally bored.
We all decided to go back to the barns to look at the horses, and as I was walking through with my friends we noticed a bunch of the track barn workers off to one side. I didn't pay any particular attention, as this was 1979, and around work was deep in the closet. Anyway, I ducked outside to have a smoke, and one of the workers came up to me and said that he had seen me in the orgy room at the barracks (a gay leather steambath) the previous weekend, and wanted to know if I'd be there that coming weekend.
I said yes, we hooked up, and actually dated for about 3 months. I never did remember seeing him there before, and he said that he always wore his cowboy hat, and I KNOW I would have remembered that. Unless my eyes were pointing downward.