Memorably expensive meals
Luckily, I didn't have to pay for either of the most expensive meals I've ever had. Dinner for three at Le Cinque in Paris last week (the smaller of the two tasting menus, plus an extra course, with wines by the glass chosen by the sommelier) probably would have cost about €900 - 1.000. I was with a travel-writer friend and his mother, and we were comped. It was by far the best meal of my life.
A few years ago (before the bubble burst) a client took me to the French Laundry for the second-best meal of my life. My client was in the wine business, and a semi-regular at the Laundry. It was a real boys'-night-out, with about two bottles of really good wine per head, and a check well above $2,000 for four people.
The biggest check I've paid personally was at home in Los Angeles, for myself, my travel writer friend, his mom, and two other friends. I took them all to dinner at Patina and a concert at Disney Hall as a Christmas gift. Dinner and the tickets (I forget the breakdown) came to about $1,500, and it was worth every penny. I'm repeating the experience on Sunday with a different friend, although this time I booked a matinee concert so we can linger at Patina...