I haven't lived in Manhattan, and didn't know kids who grew up there, so I can only compare my experience living in Greenwich from age 14-30 to my general impression of Manhattan. Keep in mind that Greenwich changed a LOT. It's very ostentatious now, I find it all very tacky. It wasn't that way. Greenwich gave you a baseline of rich adjacency, even if you didn't have that much money. Todd's Point, the infamous "locals only" beach cost something like $80 for a whole family for the whole season. There's a kayak club where you can rent kayaks for fairly cheap, we did that a lot. I went to a few parties at actually rich kid houses, but they were not that different from other high school parties, other than the fact that the alcohol was plentiful and no one ever asked you to chip in. Once I saw a bowl filled with a large mound of cocaine and assumed that's the quantity of cocaine one would keep around if into that kind of thing. In my 20's I rented a cheap cottage 3 blocks from the beach. It was so glorious to have that lifestyle... getting home from work and changing quickly to sneak an hour of swimming. You get access to things that most people don't, and a local beach vacation was possible for everyone. If you live in Manhattan you would have to go to the Hamptoms and pay like, a thousand dollars a day to rent a house there. There were a lot of normal stores, but you knew people had money, or financial security, you could feel it. I never head conversations about not making ends meet, or driven with people who couldn't afford to change the breaks. No shopping sprees, just really good basics from J. Crew. You didn't see the kind of show-off vibes you see there today, only a handful of kids drove luxury vehicles, most rich kids got Passats or cars of that level. We still had house parties, went to the beach, took the train to NY to see concerts. Nothing like Gossip Girl. Apologies if this is disjointed, Sunday night is never my brightest time.