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I would add that there are 10x more people living on Long Island than in Westchester. So if the number of people complaining about Long Island is about 10x, then you're simply seeing the numbers play out.
Fairfield County, Connecticut has more in common with Westchester County IMO (compared to Nassau County, etc.). Out of town execs (that don't want Manhattan) are usually hard pressed between these areas when they have to choose.
I lived in long island for a few months and everyone seemed like they had something wrong with them.
All of the people I met seemed like they did not want to have conversation with me and seemed very weird. This is completely different from CT where everyone is very friendly.
Most of the young people I met seemed to care a lot about fitting in with the crowd like it was extremely important. Also many of the young people did not have a good plan for the future like most in Westchester / Fairfield do. Like for example a 27 year old shotgunning natty lights with a bunch of college kids is common in long island but not westchester.
After moving to westchester everyone is very friendly, although there are not many young people where I live my neighbors are very nice. My entire town shuts down at like 7pm and there are no cars on the road and its so quiet. I love westchester so much.
Long island is also more crowded and congested, and queens basically overflows in to Long Island, and its more like living in an extension of queens unless you go far out. (I don't even like the hamptons ) The same kinds of problems you encounter in NYC you have in long island.
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