If you want to pretend like you're in the upper crust... go to Ruth's Chris. It's one of the best places to get steak in the city.
The side dishes are priced individually, and are more like a family dish variety. I'd rather focus on the steak and dessert, rather than have a head of lettuce cut in half with some dressing.
There is also guy in a uniform that essentially watches you eat. He comes over with a little tiny brush and tray and rids your table of crumbs, and your glass never gets half empty.
Expect to spend at LEAST $50 a head and the dress is business casual.
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