A cool place to live. Very fancy and expensive.
New Caanaan is Great.
by Hailey April 05, 2005

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new canaan is a town of rich preppy bitches who think they're the shit because they have money. i live in new canaan and my whole life ive just wanted to leave there. the girls dress in abercrombie and juicy couture walking around with high wasted skirts, while the boys try to be black although less than 1% of new canaan is actually black. they have no idea what the real world is and is scared to go to stamford. the moms are all hot because its all botox and fake blonde hair, always going for manis and pedis with thier children starting at 4 years old. most of nc moms dont work and if they do its in real estate which isnt even a real job..they just do it to say they work. they spoil their kids and buy them range rovers whhen they turn 16. in one word new canaan is full of homos.
my fucking life in new canaan
by hatencforeverrrr September 05, 2010

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A stuck-up preppy town that is loaded with cash located in conneticut. On Friday’s after school, kids walk into town, crowd around Mackenzie’s and smoke pot, show off, and get drunk. The town has no clue what poverty is, and whenever they have fund-raisers for the homeless, some crack-dealer kids steal the friggin money and buy cigarettes. The mother’s have no clue how to drive what so ever and once in a while, they run over a poor bulimic runner in a rush to get their nails done. And sports aren’t for fun here, they’re for competition. Everyone is on a sport team, and if you aren’t on one, you are considered a gay loser. Aren’t kids nice here? All of the girls obsess about how they look and mostly spend time in the bathroom making sure their hair is perfect. Yeah, I almost became one of those, but I’m not. I’m also not emo, either, which are the only two classifications in New Canaan. And there are the butt-kissers, too, but they have no life. People in New Canaan have more then one house and brag to everyone about their money. And most of the time the parents are sitting around drinking wine while their kids run off and smoke.
On the last day of school, two stupid seventh graders got in a fight and were arressted, a kid stuck his foot in a window at B&R, and everyone wears really tight clothes. Great for New Canaan!

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Home of the "Gang", a group of Juniors who feel the need to talk so loud that the entire lounge hears. While speaking to their friend who is 2 feet away from them, they tend to shout and look around the lounge to make sure people are looking at them and to see who is listening. Most of time people are looking, only not out of envy, which they think people are, but more-so thinking to themselves "would they please shut up?". They also feel the need to shout about their drunken/coke-infested/high weekends, thinking that no one else does these "rebellious" things. Well, we're all laughing sooooo hard right now! We <3 the gang!
"OMG do you remember falling off the chair when you were SO DRUNK on friday?!"
"ahaha no, i fell off the chair?!?" (this all being 2 feet away from each other, shouting, so everyone else hears)
by tori spelling!!! April 24, 2005

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tori spelling, stop writing about the gang, everyone gets it, they're loud, if they piss you off go talk to them in person.
omg the gang was so loud today im gonna go home and write about it on urbandictionary.com
by a junior April 27, 2005

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New Canaan is one of the richest towns in America but the people there can't get over themselves. Being one of the few people in New Canaan who doesn't have 6 houses and multiple Bently's, I can laugh at the comedic antics of my classmates and people in the town in general. In New Canaan, people try to be badass by skipping class and listining to rap. Well look in the damn mirror everyone in this town is friggin white. As for sports, if you dont play baseball (best sport) or lacrosse (stupid) you are considered an outcast or faggot. But in New Canaan, talent has nothing to do with sports. You will only get playing time if your parents are friends with the director of your sports, or politics. I am one of the few who suffer from Parental-Commisioner-Enemy-Syndrome, or PCES. All of the others who suffer from PCES share my synical veiw on my disgraseful town, but at least we are better then the D-Baggers
New Canaan is not where you should move. Waste your money somewhere else. Seriously.
by newcanaanbaseball July 10, 2008

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whoever wrote number 5 is the man, it was prob some unrisque senior who cant compete with the cool sophs, so sit down.
am i not a risque kid???
by risky April 04, 2005

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Home to the private school St. Luke's School: the biggest drug/ alcohol associated school in the country. People from all over lower CT (and even NY) attend SLS and play many sports/arts, take hard ass courses, and get high and drunk as much as they can...and then some. Home to the fighting Crusaders.
"Dude, another St. Luke's School student got thrown out for being drunk in school!"
by Ja.Co April 04, 2005

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