Hmmm.
Most expensive meal I had was $1650 for 2 people at Bo Innovation in Hong Kong.
I've covered the tab for bottle service a couple times. That was a couple thousand each time. I've also had the tab covered for me as well, so if you even all that out, probably less.
I'm about to go to Dubai where for 2 nights our hotel will be costing $3500 a night (could only afford 2 nights so we'll be going to another hotel after), so that will probably end up being the most expensive night out as dinner will probably be expensive too, and we'll probably get champagne if it's not covered. So I'll report back in a week and a half to let you know what my most expensive night was.
EDIT - The hotel includes a Rolls Royce Phantom driver for your stay

First time I'll even see that car.