I spent 5 years of my life in Chicago. It was a potent time, full of risks, and excitement – I had so much fun I wanted to DIE, and I had so much heartache I thought I might actually die … It was a landmark in my life.

I felt I had to move on. Some stuff went down in Chicago which made it impossible for me to imagine living there anymore. (At least living there and being able to have a normal happy life.) GEOGRAPHY was the problem! Yeah, that’s it…

So I moved.

Chicago, over the years, has continued to call to me. It’s a memory, a mood, a symbol … It represents for me who I used to be. Well, it represents a lot. Youth, fear, growth, love, tears, howling laughter, coming out of my shell … All of this huge stuff happened to me while I lived there.

I have yet to feel like I have gained back whatever I lost when I moved away.

However, on the flipside – if I hadn’t moved to New York, I wouldn’t be so near to my family now, which I love … I wouldn’t have met my dear friend and soul-sister Jen, I wouldn’t have met my crazy Texan cowboy friend Wade – I wouldn’t have met Rich … oh, and so many others.

But the feeling of Chicago? The feeling of youth? Of insanity? Of spontanaeity and unabashed joy?

I’ve had a rough last couple of years. Really rough. Thank God for the blog, that’s all I have to say.

I haven’t been back to Chicago since early 2001. My relationship with the city is now tumultuous, and kind of … haunted. For a while my feelings about Chicago were all tied up in one person, and I couldn’t think of the place without thinking of him. My entire time in grad school I would spend my vacations in Chicago … I had so many old ties there, so many dear friends … and not just that … but I LOVE that damn town. The lakefront, the skyline, the people … It’s one of the nicest cities I have ever encountered, certainly my favorite place I have ever lived.

So then why not move back?

I suppose because I know, in my heart, that … a part of me (if I moved) would want to “go back” in time … Like: If I moved back there, perhaps I could capture again the feeling of when I first lived there, a crazy time – I moved there on a whim (brought about by my Westfalia breaking down) … I walked away from my old life and started a new one. Quickly. I started brand new in a city I had only visited ONCE, and that time for less than 24 hours. It was a risk moving to Chicago. Although I had dear friends there, I had no idea what, exactly, I would do there. I had no idea what I was looking for.

I found so many things during my time there. So many things.

I was in amazing plays, incredible projects … All of my friends were too.

I had old friends there. College friends. A whole crowd of us had ended up in Chicago … Like, my best friends in the world. The fun we had was apocalyptic.

And I made new friends. Kate … Ann Marie … Derek … George …

There was the triumvirate. Spectacular men. All of them. I wish I could see them now, and hug them, and thank them for all that they gave me.

But the city I am going back to is a different city now. Friends have moved on. One of the triumvirate guys is still vaguely in the vicinity but it’s really not a good idea for us to be in contact at all. The other two have long since moved away. The landscape itself may be different – new buildings, old favorites torn down … but it’s really the people, (I used to think of them as “constants”), who will have changed.

I used to return to Chicago, like clockwork, on my vacations from grad school … and I would make the rounds. I knew where I would inevitably find people.

Oh, on this night? So-and-so is bartending so I’ll just stop by.

And on this night? He’s got his weekly show at such-and-such … I’ll stop by.

I absolutely LOVED that. In a world of flux and loss, it is wonderful to count on such small things. Over 3, 4, 5 years, none of that changed. I could go home to Chicago, and slide back into my old role … there was still a place there for me.

Well, the constants are no longer constants. I don’t know where to find certain people anymore. In growing up, there have been breaking away of connections … some of them quite wrenching.

I suppose Chicago, and my love of it, was never really about the city itself anyway. It was the people I met there, and the girl I was while I lived there, and the people who randomly came into my life BECAUSE of the girl I was then.

I don’t know what has happened … or what I have lost … or if I have gained anything … I can’t tell anymore … I feel very very stressed out right now, and very anxious about traveling … and suddenly today I feel this overwhelming sadness. Like a huge wave.

I am feeling anxious about returning to this place, this pivotal place, and to find it changed. But more than that … I suppose … I am afraid to be confronted with how much I have changed. I don’t know why that’s so frightening to me … but it is. I have been so frantic the last couple of days … bridesmaid stuff – dress – shoes – preparations … that I have not at all been aware of my inner life. I knew I was extremely anxious and unable to sleep. At all. But I just thought it was because of money worries, and the normal stress before leaving for vacation.

Today, though, talking with Jen … it all came flooding out. Surprising me as much as her.

“What will it be like to go back to Chicago and have so-and-so not there??” Tears. Major tears.

I suppose this is good information to have – so I won’t be completely blindsided at my first view of the Chicago skyline. Now I know.

Now I know what is going on inside of me. It takes me a while sometimes. I’m not all that self-aware. At least not about stuff like this.

I don’t know what it will be like to be back in Chicago … and to not see so-and-so … and to not do such-and-such … But maybe I need to have this one week of … getting to know the place as a new city, perhaps a pure city … with no preconceptions, no baggage lugged along behind me …

Maybe someday I will be able to visit Chicago without seeing my entire life flash before my eyes.

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19 Responses to Chicago

  1. DBW says:

    It’s always the people, Sheila. You should know that. Go back to an old neighborhood from which everyone you knew has moved–it’s almost as if you never lived there. Go back to an old haunt/bar. It’s not YOUR bar anymore, it is THEIR bar–the new people who frequent the place. The older one becomes, the more difficult it is to recapture an attachment to any place, no matter how intense the attachment. That is a sad fact, at least in my life, and I am more nostalgic than most. However, there are always great memories–I hope you enjoy your time in Chicago. It is one of the great American cities.

  2. Jon Barnard says:

    Hi Sheila. I’ve been reading you for a long time but have not felt moved to comment before.

    Posts like these make me think of the scene in Swingers when Vince Vaughn is chatting up the girl with a cigar. (I hope you’ve seen it.) She’s telling a story of a childhood crush that ended with an embarrassing rebuff. At the end of the story her teacher says to her, ‘Dierdre, you’re so dramatic. You should become an actress.’ So she did. (Not that I’m comparing you to her – she was rather offputting.)

    Sheila, you’re so dramatic. No wonder you’re an actress. I love reading about the way you experience your life so passionately. I’m not like that at all; I tend to crave stability and equilibrium, which can make life rather predictable and flat. You’ve obviously had some bad times, but I think they are the price you pay for living richly. I think it’s a price worth paying.

  3. Curtis says:

    Loved this post, in a heartwrenching sort of way… I feel the same about my time in Rhode Island… I recently stopped by to visit my old friend while I was on business travel in Boston. We chatted a while and went down to the Mews (you must know the mews!) and it was great to see him again. There used to be three of us that would always hang out… I think we were both looking for our friend who wasn’t there, thinking about what wise-ass comments he would have made, wishing we heard them in person rather than in our head. Nostalgia about a place is so difficult because the memories of each place are so wrapped up in the people you knew there. I miss the place SO much, but without the people it is just hardly the same… And you can never go back to where you were then.

    Good luck in Chicago. I hope the tears you shed will be tears of joy for times gone by.

  4. red says:

    DBW –

    You say to me “You should know that.” But I admit, freely, that I’m not all that self-aware about stuff like this. I rarely know what is ACTUALLY going on with me. Oh well. Now I know!

  5. red says:

    Curtis – You are blowing my MIND. The Mews!! It’s right down the street from where I grew up. My sister worked there. I absolutely love The Mews. It’s like “where everybody knows your name” … I go there when I come home and it’s like a high school reunion.

    I didn’t know you had such a strong connection with RI! (Although I don’t know why this should surprise me since … I really don’t know anything about you at all … heh heh … except that your wife’s name is Sarah and she has obviously read The Color Purple)

  6. red says:

    Jon –

    Muchas gracias, my friend. What a nice comment. And thanks for reassuring me that I am not like that chick with the cigar – although that scene was SO DAMN FUNNY. Didn’t it have Jaws music underneath it? Am I right?

    Anyway, thanks. :)

  7. Curtis says:

    RI is probably one of the things that attracted me to your blog. That and the excellent writing of course! :-)

    I did my undergrad at URI, and have many, MANY, fond memories of the Mews AND Rhode Island. I need to get one of those “Have Beer, Need Beer” license plate things for my fridge…

    I always toy with the idea of going back to URI for another grad degree… but the time has really gone by. My friend is retiring and the people just wouldn’t be the same… But damn do I miss it!

  8. red says:

    I went to URI for undergrad, too. Beautiful campus, huh?

  9. Curtis says:

    Loved it! I loved reading on the quad when it was nice out. It would be beautiful there today I bet.. Leaves turning. Cool and clear fall day… I had a lot of classes in those two buildings on top of the quad.. I forget there names, the one on the left was the physics building, and the other I think was just generic classroom space? That was one of my favorite sites, sitting in the quad with those beautiful granite buildings staring down at you.

  10. red says:

    Yeah, those big stone buildings … lovely. I was always over at the Fine Arts Center … I was a theatre major, so we were shoved off to the side. Heh. But the Fine Arts Center is a fantastic building itself. And Will Theatre … what an AMAZING theatre. It was almost Broadway-size … A great experience for college actors to have to fill up a huge theatre with their voices, their acting, etc.

  11. Curtis says:

    I can imagine, I went to a Macbeth production there. Really great show. One of my friends was active in the theatre department. I watched her in a couple shows.. (She was mostly in musicals though, which typically don’t excite me as much). :-)

  12. Why I love reading Sheila O’Malley’s writing

    It’s because of postings like this. Hey, we’ve been posting a lot on politics as of late, which is kind of unavoidable considering that what I teach and that’s what Robbo does. And we’ve been getting some nifty traffic as…

  13. michael says:

    You used to be in a shell?? Hard to believe. Anyway, this post reminded me of when I lived in Chicago. It was early 70s and Chicago had a VERY lively folk/rock scene. Little music venues everywhere. On this particular Sunday, my friends (a married couple) and I went down to Old Town to neb around when I began to rain so we decided to stop for a beer. We went into the Earl of Old Town and sat at the bar. As we nursed (yeah, right) our beer a young guy walked in and said to the bartender, “Mind if I practice a little?” The barman said, “Sure, Steve.” He went up to the stage, turned on the sound system, got out his Gibson “Humingbird” and began to play. SONGS. I. KNEW. “City of New Orleans,” “Would You Like To Learn To Dance?,” “My Whole World Lies Waiting (Behind Door Number Three),” The Lincoln Park Pirates.” It was Steve Friggin Goodman. And he played and sang for an hour, or more. For the three of us. And the bartender. As it rained. In Old Town Chicago.

  14. michael says:

    That should read “it began to rain.” I haven’t rained in years.

  15. red says:

    Oh, Michael. What a beautiful story. Fantastic!!

  16. Chrees says:

    Sheila, in Lilek’s Bleat today he has a section that complements yours at some places:

    “Going back to an old home is full of moments like that, and they all remind you of the same blunt fact: you belong to places, but places don’t belong to you. They change as they please and couldn’t care less what you think.”

    I thought it funny that I should read your post and his so close together…

  17. Jon Barnard says:

    Yes, that’s the scene with the Jaws music. Vince Vaughn gets her number then turns away and rips it up. It’s a great scene, but not as good as the one with the answering machine. Every time I watch it I tell Jon Favreau to hang up and go to bed, but he never does.

  18. red says:


    Intersting that you noticed that – I did, too. While I love all of Lileks’ writing, especially when he goes on a rant … the real reason I like him is how he constantly acknowledges the strength of his attachment to place. I love that about him. He visited NYC last year it was, I think – and his post about the architecture here made me see my own city in a new way.

  19. red says:

    Jon – that scene with the answering machine is classic in so many ways. I CRINGE when I watch it, and yet I cringe not just because I’m embarrassed FOR him, I cringe because I RELATE. Even if I haven’t behaved in exactly that way … I so relate to that frantic vibe he has. How you live out the totality of a relationship before the first date, etc. etc.

    But what’s so AWFUL is that he actually DOES IT, out in the world, INTO HER ANSWERING MACHINE.

    Brilliant. Just brilliant.

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