7 Years a Midwesterner: A Bostonian’s Departure and Return to the Greatest Little City on Earth

Hey everyone, I want to start off by thanking Matt Flynn for giving me the opportunity and the venue to get my first blog out there. When Flynn told me he was going to have a themed week about Boston, I knew I had throw my hat into the mix. This might be one of longer blogs, but bear with me. After spending close to a decade in a foreign land, you pick up a few things that stand out. I wrote this with a stream of consciousness so bear with me.


Up until last July, I spent the last 7 years in the Heartland of America. The front end of those seven were spent wandering about the city of Chicago, with the last two and a half years were out in Milwaukee.

 My decision to leave the Hub and try another place started my junior year at BC High. Like most other BC High underclassmen, I had my eyes set on Boston College with dreams of going to football and hockey games at the Heights. That went out the window when I was in my group guidance class where my teacher started writing on the whiteboard names of Midwest and West Coast Jesuit universities with scholarships

 Free money for college? I’ll hear you out.

 The college at the top of the board was Loyola University Chicago. She told us the school was right on Lake Michigan, a few stops away from Wrigley Field and about 15 minutes from all the action downtown. I wrote the school down in my assignment planner and when I got home that afternoon, I did a quick google search. The first few pictures roped me in. The blue water of the lake, the Skyscrapers made famous in John Hughes flicks, the bars and restaurants of Chicago had me day dreaming. I thought I would never want to leave Boston, but after getting a piece of the outside, I needed to try something new. Four years away from home could be good for me. I highly recommend leaving your home state for college. It gets you out of your normal attitude and allows yourself to take chances/risks/guesses you might not have the courage to do in your own backyard.

 On August 20th, 2008 I boarded a plane at Logan Airport bound for O’Hare. When I landed I was scared shitless. I was carrying all the clothes and school supplies for the year and took a seat on my duffle bag for about 15 minutes; not sure if I could make it here. I already felt like I was in a different country. I was hearing thick Chicago accents (think “Bill Swerski’s Super Fans”) and not a fucking Dunkin Donuts in sight for a large hazelnut iced coffee. Luckily, I found a dunkies and a crisis averted.

 After a few weeks on campus, I caught on that I have become the token Boston guy and resident defender of all things East Coast: “Hey, are you like a huge Red Sox fan?” “Dude, you must love the Dropkick Murphy’s so I’ll blair ‘Shipping Up to Boston’ every time we hang out.’” “My friend said you’re from Boston! Say ‘Pahhk tha cahh in Hahhvahhd yahhhd!’ It sounds so weiRRRd.” “The Patriots are cheaters and Tom Brady isn’t the greatest QB in the NFL” (I felt chills writing that).

 It was the first time I ever felt like an outsider. I had the understanding that the US is one giant country, and beside the South, Americans were for the most part the same. I learned the first year at Loyola that people from all over the country had this skewed conception that all people from Boston/East Coast are hard-asses/short/cold/no-bullshit type personalities. To quote Good Will Hunting: “You think I know the first thing about how hard your life has been, how you feel, who you are, because I read Oliver Twist? Does that encapsulate you?” Most people from the Midwest are very “normal”; they’re bland as vanilla ice cream. Outside the metropolis of Chicago, there’s nothing to do. I’m not kidding, when you’re about 30 minutes away from city limits, there are corn fields and silos as far as the eye can see.  Most of their idea about the world come from Hollywood. So when someone from Peoria, IL or Prarie du Chien, WI met me at Loyola, they thought of The Departed, Mystic River, Gone Baby Gone, and so on. When people would ask me if I knew people in the mob with a smirk on their face, I would ask them if their lives were similar to “Children of the Corn.” Living in Wisconsin for two years showed me that it wasn’t far from the truth.

Some major differences between Boston and the Midwest:


Living in the Midwest for the last 7 years, I’ve definitely picked up on a few habits, one being the hospitality and their openness with strangers. There have been countless times while I was at school in Chicago or working in Milwaukee when you’re standing in line somewhere and you see (more like feel) a person gazing at you. More often than not, he or she would strike up a meaningless conversation for the next fifteen minutes, going on and on about God knows what. This would never happen in Boston. You could be dying in the street begging for help and people would take one big ol’ step for humanity right over you.


I have yet to go to a city where their sports are live or die. The only place that comes close is Green Bay, Wisconsin. People are literally buried in Packers gear. I’ll give it to them, because that’s the only thing that have going on. So when the Pack don’t make the playoffs, the governor should just call a state of emergency and make drunk driving legal for the next 48 hours.

Boston is an anomaly with sports. I can’t think of another city, state, or region that has had the success the Boston faithful have had. For that, outsiders can’t handle/stand us. I’ve been called spoiled, unappreciative, a cheater, and just lucky. Yeah good luck with that, not going to hurt my feelings. I don’t bruise like peach. I know what we are. We’re the best. It’s not debatable. When people from around the country would bitch and moan about the the Red Sox, Patriots, Celtics, Bruins, I’d just smile. Keep taking swings. We’ll just add more hardware to our trophy cases.

The Tide:

Have you ever been driving along the harbor around Boston, look at the water and announce to whoever you’re with the level of the tide? “Hey look, it’s high tide, ” And the person next you you nods in approval of your observation. This is a completely foreign concept to people outside of Boston. I said this once in Chicago (yes, the Great Lakes are big enough to have tides) and I got a look like I belonged in an institution. In Boston, it’s almost weird if you didn’t say something about the water level.

Last but not least, the Boston accent:

Ah, yes. The Boston accent. I’ll put it out there: it’s impossible to pull off if you’re not from the area. Anyone can pull off a southern or Chicago accent. Boston’s is something special and we’re protective of it. We can’t handle when people fuck it up. Leave it to the pros. After being away for so long, one of the first days back I went to a corner store to pick up a few things. As I stepped up to the register, the lady at the counter said in a raspy smokers voice, “Mornin’ hun. Howahya? Will that be all?” Brough a smile to my face. I know once I post this there’s going to be about a hundred more things I wish I added, but I’m not forgetting this: I’m glad to be back. Boston, you’re my home.


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