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Carmines could work, its all family style big portions, so it would average out to $15/plate. But you couldn't get separate checks. Its also pretty nice, the one in times sq always has a dressy theater crowd.
Someone else mentioned Gonzalez y Gonzalez (broadway & houston) it's decent inexpensive Mexican food and has a fun atmosphere, also you can get pitchers of margaritas for cheap. You wouldn't be too out of place in your dress.
Do restaurants even give 4 checks to a party of 5? I have never in my life been with a group that did such a thing. Definitely tacky. I'd be careful with the Greygoose idea too, that could be embarrassing if they caught y'all.
If you like Italian food, try Carmine's on Broadway & 90th Street. The food is great and the atmosphere is very nice--large and attractively decorated. It's not really elegant, but you wouldn't feel strange if you were well dressed. You could eat and drink for $15/person, but that would probably mean skipping appetizer and dessert.
I will second Carmines. They serve family style so you get more for your money. The food is also pretty good.
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