Chicago Is A Kick Ass City! (IL) “DAY 34” – 8/7/10

August 8, 2010 - 10:16 am - (Chicago,IL) “DAY 34”

I left Gary, IN a day earlier than I normally would have.  I didn’t have a place to stay for Sat. night and to be honest... I had enough of that area.  I’m in a losing streak and the scene wasn’t for a younger guy looking for ladies :).


I did have a good time though and the poker room was nice, the cards just weren’t going my way.  As I left, a guy who worked there (Ernesto) helped me out out with my things.  We spoke about my trip and when I tried to give him a tip... he wouldn’t accept it.  Thanks for your help while I was there.

I told you yesterday, how my friend from NJ (Monkey) hooked me up with a place to crash in Chi-town for Saturday and Sunday.  He called his old college roommate Keith,(Wesley ,(DE)) and set it up for me.

The good thing about being in Gary is that I was only 20 miles from Chicago or... a hour and half :).  The traffic was similar to that of: driving from New Jersey into New York City.

As I entered the city my brain went into sensory overload!  The first thing I saw was the where the WhiteSox play, then I saw the park where Lollapalloza was going on (awesome :)).  I kept driving north on the water (Lake Michigan) and it looked like a beach area where everybody was partying or jogging or something... This city is great!

Unfortunately, parking is also similar to New York... a real pain in the ass!  None-the-less, I found a spot near Keith’s place after about 15 minutes.

Keith and Marley

Finding a Place To Stay
Now, I haven’t seen Keith in many years although I have heard stories about him through our mutual friend (Monkey), as I’m sure he has about me too.

I walked up to Keith’s place where he was waiting on his front porch with his dog (Marley).  He was excited to have me in town and was ready party all night!  Nice!  I need a day like this.

I got situated,. then we went to our first bar of the night.  It was called Houndstooth and it was a just a block from where the Cubs play.  The Cubs had a day game today

Chug it Kristen!

(Sat.) so the bar was filled with people who just left the game.

The cool thing about this place, other than the fact it was filled with people singing and dancing was... they served 40’s in the bar.  So cool, my boy Deniro would love this!

Meth is a hella of a drug!

Almost forgot... before we entered the bar, a drunk lady (I think she was on Meth. though) approached us and asked Keith for a cigarette.  She was obviously on something as she rambled on about her day.

She said she was taking her dog for a walk but had no dog.  Then she said she was the V.P of something and talked a little rational for a moment.  I was confused... but the one thing I did I did know was... that she loved F%@king men! lol


Festival - Cities Big Event
We drank a 40 between us and headed off to a festival about a mile away (walking).  I saw a festival only a few blocks from where we were and I started to walk toward it until I looked closer at the sign.  It had rainbows on it... huh? Yes... it is a gay pride festival.

I don’t care if anybody is gay but if I’m trying to find a date, which I am... then this isn’t party I should be looking for one at.  I may get a surprise when I check under the hood! 🙂  Not that there’s anything wrong with that. 🙂 (Seinfeld)

Anyway, we continued on to the festival we were trying to get to (Retro on Roscoe).  When we arrived, it reminded me of any NYC event where the street was blocked off.  Nice!  

At this point, it was around 8pm and we were hanging out with a bunch of Keith’s friends  as we walked around checking stuff out.  I got a monkey balloon in honor of... the Monkey’s gesture for me.  Thanks again Monk!

Then, somebody got a text telling us there was a rooftop party overlooking the festival and we were invited.  We headed over there to check it out.  The directions said, just take the elevator to the fourth floor and nothing else.  I was thinking which apartment number?

Well, there was no number... the whole 4th floor, plus the rooftop was one place.  What a kick-ass set up.  From where we could see the band playing on the street as well as the Chicago skyline in the distance.  Awesome!

The party was stocked with everything you would need; food, beer, wine, alcohol... whatever, it was there.  Then, I saw something I have never seen before.  A dog who was at the party started to take a piss on the upstairs deck in front of everybody.

This wasn’t the shocking part... the shocking part was that this dog pee’d for over 2 minutes straight!  The whole party was cheering him on as he was breaking records right before our eyes!   

Seriously, he pee’s for so long that people who were downstairs had time to make up the to the roof to see the end of it!  The place was laughing as eveybody cheered when he finished!  So funny! 🙂 (I should have had my video camera. Damn!)

Oh yeah, the party for was for the guy who owned who place, it was his birthday.  His girlfriend bought him a cake of her boobs, it was a hot looking cake!  Nice rack Mrs. Pastry! 😉

And I also took a picture of me with the tallest guy (6'10) I have met on my trip (so far).  We talked for a bit and he was also named Dave.  Good luck in life big man!

At the party, I met a bunch of different girls who were all out to have fun.  One girl was named Dana, she was real cool and actually had a good sense of humor.  She throws a massive party every year called Heff-Feast, I’ll be there next year!  You can count on it.

Chicago Skyline

Then I hung out a girl named Kristin, she is going to New Jersey this week to hit the shore.  Man, that “Jersey Shore” show has really hit the nation hard.  Everywhere I go that’s the first thing I hear when somebody finds out I’m from NJ.

455 West

Anyway, we did shots and talked about how NJ really is.  She was a cool chick and I think we are gonna hang out before she leaves on Wednesday.

It was after 10 pm... time to go to another bar.  So we jumped in a cab (30 minutes later we found one) and headed to 455 West.  It was a clubby bar and the people we were gonna met had already left, so we got into another cab and headed to different part of town.

The area we wound up at was filled with drunk people having a blast.  Keith knew the girl who was running promotions at this bar so the drinks were... on the house!  Nice!

We stayed there until 2-3 am and then we mulled around the street looking for random drunk girls.  We thought about getting some pizza but it was $5 a slice.  Ridiculous, I wouldn’t pay that much for a slice even if I had a million dollars!  (it wasn’t deep dish either, imitation NY style.)

Anyway, at this point, both of us were drunk and tired so we headed back to the pad to crash for the night!

Chicago is a awesome clean city.  I had never been here before (other than driving through) and I think this may be where I end up living when it’s all said and done.  So far,  the is the nicest and coolest place I have seen.

Chicago... beware!  The Rooster is thinking of making this his new home in a 46 weeks! 🙂

I never made it to the concert... but today (Sunday) I am going to see the last day of performances.  Soundgarden is the headliner and that is band I wanted to see most anyway.  Wish me luck on getting in for free!

Thanks for reading!


Comments (5)

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  1. Matt says:

    Chicago sounds amazing man. im jealous after reading this post. I gotta get out of columbus..allll in due time. This is your best post so far by the way, keep it up.

  2. Deniro says:

    40’s??? At a bar??? Best bar in the land!!! Fantastic

  3. Brian Farrell says:

    Well if you make it back to Chicago, swing by my bday party and Retro again in 2011! Enjoyed reading the story. Priceless that you caught the World Record Dog Piss. I had enoutgh time to watch the beginning, stumble down the stairs to get the hose, and still make it back upstairs for the finale. I love it that the word makes it around to good people to join a good party. We all had a blast. For the record all the booze- GONE. The cake gone too ….but I have the model to keep me satisfied! Cheers- Brian

  4. Dana Carideo says:

    Hi Dave- Is it Dave “The Rooster” or “Rooster Dave”? Well It was very nice to have met you, I came back to roof party with my two sisters and A girlfriend. You were gone…I am not sure if you are still in Chicago but, If you are lets hang. If not Heff Fest next year will be a blast. You can email me at I hope all is well, Dana

  5. dave says:

    Thanks for stopping by Brian. I thought the party was awesome as you could tell from my post. I don’t where I’ll be in a year but if it’s anywhere near Chicago… I’ll be at your birthday party again! Thank you for having me!

    I can’t beleive I didn’t have my video camera for the world’s longest dog piss… Maybe nexy year!


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