I don’t have any really funny dating stories personally, the worst that happened to me was getting lost in central park.
I took a girl to central park, my plan was to walk through central park from top to bottom (the top being the side further from Brooklyn, it’s the top when looking at a map) I don’t have the best sense of direction but I figured that we could stay on paths closer to 5th ave then exit on e 61st there’s a very fancy hotel. While walking through the park trying to stay close to 5th ave we found ourselves walking on dirt paths which made me feel bad because she was wearing fancy shoes, so we looked for paved paths and before we knew it we were lost, this is evening time, not many people around and it’s getting very dark… Later that night in the hotel I proposed and we’re engaged.
Truth be told I did handle the situation very calmly, we asked for directions, followed them and made it out of the park