Not me, but a girl I was dating in Montreal when I was much younger wanted me to learn to like Scotch. She took me to a Scotch Bar and bought us a couple of Scotchs at $23 a glass. I choked it down and she went to order me second one and I said, "Save your money and just get me a beer." Looking back I can't believe how young and stupid I was. She was really good looking, had money, and was a maniac in...well, you know. I broke it off with her because I found her snobby. In hindsight, and with my newfound love of Scotch, I want to go back in time and change that decision (and I'm not talking about having the second glass).
As for the most money in a night? I was a waiter in a small resort town that had no bank, so I had to drive into town about an hour away with a hockey bag full of tip cash to make a deposit. I headed out with the bag with about $1500 dollars in small bills and made the mistake of stopping by the local bar to have a beer and shoot some pool. I woke up the next day in my car with a girl I didn't know in the passenger seat and a considerably lighter bag of cash. I don't remember much, but I do remember ordering B52s (shots) by the tray-full. Stupidity of youth, but it was a lot of fun (I think).