Dear Chicago,
You'll never guess
You know the girl you said I'd meet someday?
Well I got something to confess,
She picked me up on Friday,
Asked me if she reminded me of you?
I just laughed and lit a cigarette,
Said That's impossible to do.
Life's gotten simple since
And it fluctuates so much,
Happy and sad and back again
I'm not crying now too much.

I think about you all the time,
It's strange and hard to deal
I think about you lying there,
And those blanket's lie so still.

Nothing breathes here in the cold,
Nothing moves or even smiles,
I've been thinking some of suicide,
But there's bars out here for miles.
Sorry about the every kiss,
Every kiss you wasted bad.
I think the thing you said was true
I'm gonna die alone and sad.

The wind's feelin' real these days,
Yeah and baby it hurts me some,
Never thought I'd feel so blue,
New York City you're almost gone.

I think that I've fallen out of love,
I think I've fallen out of love,
I think I've fallen out of love, with you


Lyrics submitted by Shadee01

Dear Chicago Lyrics as written by Ryan Adams

Lyrics © Universal Music Publishing Group

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Dear Chicago song meanings
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22 Comments

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  • +2
    General Comment

    I think this was written over a period of time. HE goes back and forth with it.. " Happy and sad and back again I'm not crying now too much...I think about you all the time..." i think it is the phases in getting over someone. One day you can be fine...the next minute...you could be a total mess. I think the person in the song is still inlove... and I dont think he ever gets over her. The song is just a bunch of contradictory statements to try and make the guy believe that he is ok...and maybe somedays he is...but really...he misses her so bad that he can't stand it...well atleast that is what I think.

    Britni24on April 01, 2005   Link
  • +1
    My Interpretation

    Okay, so here's my interpretation, and it is most likely based upon my own life experiences, as most interpretations are... butttt Chicago and New York are actually two seperate people. Chicago is the person that he just recently broke up with, the one that it's still so fresh that he's still trying to cope with it and he thinks he's close, but he just keeps fluctuating and everything reminds him of her.

    The last part:

    "The wind's feelin' real these days, yeah and baby it hurts me some... Never thought I'd feel so blue, New York City you're almost gone.

    I think that I've fallen out of love, I think I've fallen out of love, I think I've fallen out of love...with you"

    Is talking about an old love, perhaps a first love (at least for me :) ). That person who you never thought you could get over, and probably even still thought about throughout the aforementioned love, the person who you always seem to compare everyone else to, and yet some how that person is almost gone from your memory. You're finally reaching that point where you can let go of that person, where you've fallen out of love with them and can feel the wind of others- but it's a melancholy feeling, because you got so used to missing them that now you're missing that loneliness that came from loving and missing them- it became a comfort zone, and now it's almost gone as your love for them has ceased.

    lmac5on November 17, 2008   Link
  • +1
    General Comment

    I can't believe this is the first time I've heard this fantastic, brilliant track.

    I can't get enough of it.

    Definitely for me, a dude getting over previous loves and meeting, and even, allowing new love where he probably didn't think it was possible. Hating yourself for still loving someone is a BITCH to deal with.

    He's a freakin' genius.

    shockdelicaon April 24, 2009   Link
  • 0
    General Comment

    Ah damn, I'm surpised that no one has written about this song yet. Well, it is hard to write about it, to be honest... its music is just sweeping and ambient... I imagine a busker with their face blued out by the cutlassing night when I hear it...

    dreamfaceon November 24, 2004   Link
  • 0
    General Comment

    i love the first verse of this song, don't even know why but it's awesome

    lilallstarmeon December 17, 2004   Link
  • 0
    General Comment

    Easily one of my favorites. A late scratch off of "Heartbreaker". Nice and depressing.

    RyDogg66on April 06, 2005   Link
  • 0
    General Comment

    This is by far my favorite Ryan Adams song. I just wondered if it's really about NYC or about a person? I always thought it was about New York, though... I mean he lives there and had that "New York, New York" song..

    ChubbyPrincesson April 14, 2005   Link
  • 0
    General Comment

    ChubbyPrincess: this song is about Amy Lombardi, the girl whose painful break-up with Ryan inspired him to write the "Heartbreaker" album. So RyDogg66 is spot-on when he says that it's "a late scratch off of 'Heartbreaker'".

    The bit where he says "Nothing breathes here in the cold/Nothing moves or even smiles/I've been thinking some of suicide/But there's bars out here for miles" is 100% Ryan. Concise, but masterful.

    Diego8978on February 10, 2006   Link
  • 0
    General Comment

    "I think about you all the time, It's strange and hard to deal I think about you lying there, and those blanket's lie so still." thats just to good...ryan adams please marry me

    Demolitionon July 10, 2006   Link
  • 0
    General Comment

    "Nothing breathes here in the cold, Nothing moves or even smiles, I've been thinking some of suicide, but there's bars out here for miles. Sorry about the every kiss; Every kiss you wasted bad. I think the thing you said was true I'm gonna die alone and sad."

    raw heartbreak.. and depression that followed it. it seems that he just can't get over the girl..

    kmson August 08, 2006   Link

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