Exact details may be fuzzy as it's been 8 years, but this was on a 1st date.
We had just walked into the Mandarin Oriental elevator. Drunk guy walks in as well and asks the girl if I'm her boyfriend.
She says no.
Brother?
No.
Oh, OK, I got it, you're a hooker. Well, I'm in room 941 after you're done with him...
Great story!
I personally went out to eat in Manhattan on the 3rd date with an out of town girl, came straight from picking her up from the airport, and when we come back outside to get our car... It was towed... with all of her stuff in it.
SO- we had to spend 2 hours tracking down the car, going to the pound in our Shabbos clothes, sweating buckets (August)...
But we got married
Thank stinks! But happy ending!
My own:
On our 2nd date, the subway car emptied out and we decided - somehow - to race down the subway car. We ran down the car and were racing hard. As she almost reached the end, the subway came to a stop and... she couldn't stop. Face first into the wall of the train. Front 2 teeth shattered in half. She pointed to the pieces on the ground as she clasped her mouth and collapsed onto the bench.
Our next date was the next morning to the dentist, and now we're married b"h.