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I would say that anybody who likes good food, is as articulate and good natured as you are, has no reason to worry in the least about feeling out of place at a Ritzy restaurant. If you ever have some mad money and want to do something special for a special occasion give it a shot. Keep in mind that a lot of these crazy tabs involve expensive booze and wine.
Just to mention an upscale chain restaurant, someplace like Ruths Chris, a couple could probably eat for about $50-60 with no alchohol. If you tell them it's your birthday or anniversary when you make reservations they will hook you up with a free dessert. : )
I had a rib eye at Ruths Chris about 20 years ago that was the best steak I had ever eaten. I was on a business trip with a 25.00 a day limit. It was right under the limit. I just kind of wandered in. Didn't know it was considered a really good steak house.
A nice restaurant is a rare treat. We have a restaurant here in Denver called The Broker. Linen table cloths and all. They used to have great food. It was around 100.00 before tip. The meal included a choice of entrees with a huge bowl of chilled shrimp for an appetizer, bread, vegetables, regular drink and a delicious desert. If you each had a drink it was about 140 with tip. They had 2 locations. The one we always ate at burned down and wasn't rebuilt. We went to the other one downtown because they were doing a free Bday meal with purchase of another. It wasn't near as good as usual. I usually had prime rib and this time I got lamb chops. I was disappointed.
Like everything else you don't always get what you pay for.