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If yuppy = preppy to you, check out the Upper East Side (70s- 80s along 2nd and 3rd Ave) - JG Melon for burgers, EJ's for brunch, Brother Jimmy's for BBQ & beers. For bars, Dorrian's and Bar Harbour, if they're both still open. This is where you'll find Ivy and similar educated young professionals (or trust fund kids) who wear Lilly Pulitzer, Brooks Brothers, Polo, and Lacoste (before it became cool again) and "summer" in Nantucket, Maine, and the Upper Peninsula.
If you want more mainstream yuppies (ie, Big Ten grads), hang out along 3rd Ave in the 30s (Murray Hill).
I heard Dorrian's is supposed to be huge for old-money types (kids that went to $40K private high schools in NYC)
Also I've heard stories about some of the Yankees hanging out over there as well after games.
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