Yowza! Nice view, I don't know if a steak is worth 40 bucks though. If you're going to go whole hog order something prepared tableside like the Chateaubriand for Two. If you get a tableside preparer with a sense of humor that isn't a tighta$$ it can be really fun. Tableside desserts are fun too. At least your getting some additional entertainment value for a $200+ tab.
You obviously haven't seen a tab for LeMont! Here's the menu:
LeMont Ala Carte Menu
If the lady comes from a well-capitalized family I'd think she'd have already been to the swank places around the Burgh. Personally, I'd find some hideyhole she'd never been to. I kind of enjoy going to lower scale out-of-the-way places with fantastic food that are lesser known and show up hideously overdressed. A tux at Premante Brothers is a hoot
Last time I was at LeMont we showed up during the dinner hour on bikes wearing ratty H-D t-shirts and slurped $20 margueritas and chowed down on oysters Rockefeller at the bar. It's kind of fun to be underdressed at a high-brow establishment as well. The valets didn't know
what to do with us when we parked the bikes in front of the door. If I recall correctly it may have been suggested that we attire more appropriately for future visits.
TL