Chicago Help Finding Entertainment for a Prospective Big Client

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Lmao this is gold. Seems like you’re being nudged into seeking out some less savory entertainment. Is there any way of finding out if the client has got that dog in him? If the client is a good ol boy maybe it’s best to just send the strip club after an old fashioned or three at a nice bar 

 

No do not know who it is. Key points are: not boring, beautiful women (a BIG problem in Chi town) and money is not an object. I'm looking for ALL options. "Fun and Exciting" according to the boss has left the city. It appears that whatever hookups the firm had, no mas. Any recommendations there? 

 Any recommendations on the strip clubs? (I'm dead serious). 

I'm assuming that maturity plus money has gotten the strip clubs and other things out of the system pretty early on. Other curiosities have also been tried and explored. If money was no object I would go after real stunning, women who bring an element of challenge in a heartbeat. I see, I want, I get. I was told that when one becomes truly successful and has real power, he welcomes a good challenge and not an easy way out for mere mortals like us. The real problem is overcoming boredom. I'm sure that places, people and women become predictable. Here lies the next problem: "we LOVE our women in Midwest to be boring and predictable," hey not my words. I don't think that this encounter is going to get that far, but just in case does anyone know of an exciting woman please do let me know. ALL sorts of excitement is appreciated. 

But just in case the meeting it is very laid back and G-rated, it still has to be quality. I don't want some chick snapping even at her boyfriend from far away, "I don't like this, I don't like that..."that brings the mood down. Or the upscale places that I had visited...yeah that's if you mange to find a human and a woman. 

live life to the fullest every single day, mm
 

Hi, Thanks for answering, no I have not. I have heard of Aire. Your suggestion seems like a great option to me personally. It gives privacy. Thank you so much!

live life to the fullest every single day, mm
 

Well hello there,

I see that you're a big fan of the show Entourage. Perfect! How would we entertain a movie star like that if he came to town? 

live life to the fullest every single day, mm
 
Most Helpful

 I went out and explored some places in the city. Restaurants, theater, and private views of the skyline are covered. The rest of Chicago is like a desert, especially for someone mature and with money. So clubs, craft cocktails, and even anything in West Loop are all boring and predictable things.

The rest of the upscale places are mostly dead and have very unattractive chicks. Oh, the places that I'm looking for has to have options of approachable "not career-focused " beautiful women, and "no girls in their 20s."

If you are trolling, this was 2.5/10, and only not a 1 just given how low the bar is for troll posts on this site. Sadly, something tells me you are serious.  

So I wonder what a guy like yourself,  a back office Analyst operating out of Well's Fargo's satellite office in bumblefuck Bollingbrook is doing planning a big night out on the town. I assume one of the Wealth Managers you indirectly work for has asked you for good suggestions. 

I love the notion that a 22 year old would have any concept of what "someone mature and with money" would even be into.  

 So allow me to recommend exactly what you should recommend to your boss for a comfortable, mature man of class: 

1. Start the night out at Beamount Bar & Grill for dinner and an initial bevvy. Often regarded for its late night degenerates staying until close around 4 AM, this spot is a sleeper pick for lukewarm (pun intended) burgers and stale ales. On the plus side, the bouncer usually has all the right party favors to get the night started on the right foot. 

2. From there, you're gonna wanna travel over to Tao. Assuming your boss is a pretentious has been with a tiny member but a big ego and a new pair of gamo loafs, he will fit right in. Make sure to pay for a table up front so he will feel the faux attention from the bottle service girls (they should really be thought of as mature women, regardless of age, actions, or any other indication of level of maturity) 

3. Once the head honcho is feeling lose, its time for the grand finale. There is no other place for a man of taste and class than the Hangge Uppe. Contrary to general knowledge, this is where the biggest deals are typically closed. Rumor has it on this very dance floor, with nose roonies dripping down their face, GS closed their last 2-3 >$10Bn deals right here. Needless to say, it is the perfect destination to wow your bosses bosses dads dad, and I have no doubt you will receive an insta promote to 3rd string Ops Analyst.

 

Thanks everyone for your suggestions. They have been most helpful. Before I go and cry in the corner...I'm still missing the women part. Out of sheer curiosity, are attractive women on Chicago an equivalent of the Republican Party in Illinois? You have to know a guy, who knows a guy ... do they even exist? 

Your Dad's Dad from Bollingbrook

live life to the fullest every single day, mm
 

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