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Ruth's Chris is great too. I was with a bigger party at Butcher and the Boar. It was damn good food too but instead of ordering a meal, they ordered several platters to pass around. Food was great but a few in the group missed having a "meal" in front of them. Not sure if that's typical or just how the leader of our group did it.
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It's hard to share a chunk of meat, IMO. Whenever I'm at Butcher and the Boar I like to get my own serving and share appetizers or veggie dishes (you know, the stuff that doesn't matter) with others. The bourbon flights are a lot of fun, but can lead to too much fun.
The various North Loop restaurants are good for checking out the scenery
Check out Black Sheep Pizza or Bar La Grassa. Bar La Grassa fills up fast and is full up hipsters and pretentious foodies but the food is worth it.
For more of a hipster-free environment, Murray's on 6th Street has great steak.