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Old 07-03-2012, 11:00 AM
 
Location: Portland, Oregon
46,001 posts, read 35,161,783 times
Reputation: 7875

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I always found Wicker Park to be a good place to get a dose of hipster that is something similar to Portland. But you definitely wont find that same mentality that is in Portland. I lived in Portland for the past decade, now live in NYC, but have a love affair with Chicago, which will be my next stop.

The thing that makes Portland so unique is that it is the perfect city to be young and clueless in. I mean that in a good way. What better city to find out who you are and what you want to do in life without having to work hard and getting a hell of a social life out of it, along with lots of drinking. As much as I love Portland, I couldn't even imagine trying to really go full force with my career choices there, but I do love feeling like a young retired person through my 20s.

Chicago is where you move to when you feel like you are ready for a big boy career and you are tired of drinking with 20 somethings.
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Old 04-10-2013, 04:11 AM
 
Location: Macao
16,257 posts, read 43,168,834 times
Reputation: 10257
Quote:
Originally Posted by Urbanite3 View Post
I can't thank all of you enough for these helpful posts. All of you have made great points.

Being a newly-single chilled out hipster, I think moving to Chicago is not what I am looking for right now. My entire family lives in the city, but everytime I visit, it's too big and cold for me. It's a great place, and will always feel like home, but the liberal, non-yuppy, friendly, care-free attitudes that people have in Portland (and mostly Seattle) are just unbeatable.
I always felt like both Seattle and Portland also have a lot of yuppies. NW Portland in particular, and Seattle just has a much more corporate feel in general.

That being said, hipsters and yuppies are kind of in the same 'family' of people, in many ways. It would be strange to have a hipster place with no yuppies among them.
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