I love Visiting Chicago, but have grown stale on the places I go and know. I tend to stay along/around the Magnificent Mile area, and up to now, it’s been great. But I know there is more available, so I began thinking. I want to hire an escort to take me on their ‘best date’ for a Saturday. I’ll pay, but I want to see places and do things that I haven’t done before. And I want it in the vein of her acting the part of a ‘hot GF’.  

Really, my goal is to learn more about places to go, things to do, etc when on a date.  

I’ve taken almost every woman I’ve been in a serious relationship with, to Chicago for a 3day weekend. I’m recently divorced and recognize she was the only one I didn’t take… because she said ‘I don’t like Chicago.’ Yes… should have been a major clue into where we’d go. But regardless. I’ve not been to Chicago on a ‘date’ for almost 10yrs.  

I contacted several Tour agencies, and was unfortunately up front with them. I had a 26yo tour guide who said she would set up a ‘day/date to remember’. THIS date was Not based on sex/interaction. I told her straight up I wanted to learn about Chicago so I could bring my date next time and know more things to do and places to go, than I do now. 12 hrs or so and I would pay her well (no sex/GF) just a straight tour for a cause. She was up for it.  But the tour company read my email, and stopped the tour dead in its tracks. Lesson learned. Don’t give details until you have personal email access to the guide.  

Anyway, I was at a loss… but then it hit me. Find an Intelligent escort based/from in Chicago, to take me on the same date. And this way… I can get more for my money… although I know there would be a lot more $$$ involved.  

I’m looking to meet someone at 10am, or so, coffee house in Intercontinental Hotel. Perhaps go upstairs for an a short BJ, just to clear my head. Then I want her to take me on a ‘woman’s best all day date’ in Chicago. I’ll buy, but she needs to have a well thought out plan to meet my needs of learning some great things to do, when bringing a civilian woman back for a date. I want to end the day with a late dinner then return to the room for a couple hour tryst.  

I want GFE for the date, as if she was truly my GF for the day.  Kissing, hand holding, touching, teasing, etc. just like a woman would be trying to entice and enjoy her man.  

 
Is this something I’m likely to succeed in finding?  
And how best to go about it?  
I don’t want to pay up front only to be ditched an hour in, because the $is in her purse.  
What should I ask and avoid?  
Options, thoughts, recommendations?
I’d appreciate thoughts from both hobbyists and providers.

Some additional info.  

I’d rather have someone more mature. 30-50yo. I’m 53 and want someone who can understand a little more, what a woman in this age range would enjoy. Honestly, while I’d date someone under 40, they would not be my preference as the gap just doesn’t work for me. But an attractive, intelligent, outgoing, 40+ would be perfect.  

There are a few on P411 which I find intriguing.  

Some advice I’ve received is to go on a regular date first, then if it goes well, discuss afterwards. That is a good idea.  

PS… this post isn’t shwing up on my General Boards list for some reason. I have to find it in MyTER. Any ideas why? It says it’s on Gen Boards on “My TER” page.

might be a better option for you.. I say, you should consider SA profile.  There is more latitude for this type of arrangement on there.

I often do this when clients visit me in the DC area, those are the best dates that I ever had.  However, I am not in Chicago.

I'm sure you can find a lovely provider to show you around town in Chicago.  Check to see if she offers an all day date option, usually 7-12 hrs plus.  Check to see if she's willing to show you around town, as some may not.  You can find this on her website, blog, or even their twitter. Sign up for their newsletter. As always, you can kindly inquire, but don't talk "services."

As for being ditched, if you do proper vetting of a provider (beyond the pics & reviews), you shouldn't have to worry about that. If you don't pay first, your date will probably ditch you and you will burn that bridge and bridges of other providers.  

Clients that book me for that, just request a 7-12 hour date, tell me places they would like to see, follow my booking protocols and then we go from there.

Hope you find someone. Good luck!

You should consider a SB arrangement.  Escorts are going to pretty much stick to an hourly basis, and since you did use the phrase, "getting your money's worth."  I assume you do not have an unlimited budget.  While providers will usually give you a rate discount curve the more time you book, it's not going to be anywhere near the savings you would get from an SB.  On the other hand, if I misunderstood your reference to "money's worth," you have money to blow, and don't mind paying a provider to watch her eat lunch, or go to a day spa while you read a magazine in the lobby, then all options are open to you.  

Even w/ sex there are some serious discounts to be had in that world. I've had arrangements with women who wanted BFs (granted they weren't hot girls, but still.. )  I've fucked women for $300-400 for overnights... (granted they didn't have car and were naive....but still). I've met some very intelligent women as well (granted they were lousy fucks.. but still)  

 
You can shape the relationship in the form that you want - at least you can try...  

 
It's an interesting world if you have the patience of weeding through 100s of women - a lot of them fakes, flakes, free loaders, and scam artists.

-- Modified on 5/17/2022 6:05:42 PM

Sounds like the storyline from pretty women.  Nobody is going to stay with you for 12 hours and not get paid her hourly rate.  You seem a bit needy and broken from the divorce.  I've been there.  Drop the coin and revitalize.  I don't think there will be a shortage of girls that will help you with that endeavor.  

I don’t know.

The whole draw to this hobby is the complete lack of connection and input. I can do a little work, and pay for exactly what I want without the input, emotions, or hassle. Don’t get me wrong, I LOVE being in a good relationship, but I’m almost through with my divorce… and I don’t feel any desire to pick up the ‘effort’ and ‘need’ of a woman. And while I could just go to a bar and pick up a one night stand… that still has ramifications. This is clean, neat, and all boxed up. My handle says it all.  

I live about 3hrs away, so I’m not close enough to ‘make use’ of a Chicago SB, nor is that what I’m really looking to get.  I’d rather pay for a 12-24hr date with exactly who I want, and she put the effort to give me exactly what I pay for. Then, when I am ready to start dating again, I’ll have that knowledge as well as have no connection to whom taught me. This hobby fills a temporary need for me. I don’t foresee it long term at all, as when I’m ready to date… I won’t have a need.  

The amount of $ my choice of wife cost me would pay for all the sex I’d likely desire for the rest of my life, with literally whomever I chose at about any moment. Paying for a 24hr high end date looks fantastic in comparison.

I guess the point I was trying to make was that the SA platform will allow you to meet a variety of women than TER - folks who are open minded to the kind of an alternative arrangement  that you are looking. You can get to know their personality. It's hard to do that w/ providers. Providers don't talk before meeting. Nothing more than perfunctory stuff needed to set up the time.  

 
I think you are getting hung up on semantics of Sugar Baby  and Sugar Daddy.  Those words mean very little. And it absolutely doesn't mean anything super emotional. I played in the SB world for 5 yrs from 2016 to 2021. I mongered very little - only when I went to Vegas and Miami.  

 
If you want to spend 3K-4K on a provider just to accompany you, by all means go ahead. You can achieve same for fraction of the cost on SA platform.  Also it doesn't matter you live 3 hrs from Chicago. What difference does that make? You have text, email, FaceTime, Duo, WhatsApp. All that comes in handy to establish rapport.

-- Modified on 5/17/2022 7:38:39 PM

I don’t feel needy. I have a desire… to learn more about Chicago. But I’m not interested in architecture nor the Pier.  

I want something that locals will know. And I want to enjoy it with a beautiful woman on my arm. I could certainly find women who would jump at the opportunity to go. We could learn it together and enjoy our time. But… that always comes with a cost. ALWAYS. They get attached, hard, and I don’t want that right now.  I want to enjoy myself, but not invest in a woman right now. Perhaps 6 mo or a year. But I don’t want to ignore the things I enjoy be it learn about Chicago or sex with a beautiful woman.  

I have no issue paying for service, so I’m uncertain your presumption that I want someone on the cheap or cut rate.  

The purpose of the post was to gain thoughts and advice on finding the right woman to meet my desires. Not upon who to use a coupon.

When you speak that kind of English.. "I wasn't no where on your mind..." Why would you be on anyone's mind?  C'mon now.. You should at least try to speak proper English.. Strive to be like Obama - not Snoop Dog. LOL...

Until I got to the part where he wanted to start at 10:00a.  Lol   If you are okay with starting that early, then of course, I would endorse you if it's the kind of date you would accept.  It sounds a little tame for you, but you know better than me how much pampering and fawning over you can take.  He sounds like a thoughtful guy.  I will tell him to eat his Wheaties first.  You should PM him and tell him you have the CDL seal of approval stamped on you somewhere and it's up to him to find it.  Lol

Hi, prob your best bet to save sum $ is to hire a local guide that would show you around and knows the city well instead of an escort to be a guide!.  and then tou can have your Tryst activities later on. 🙃

I may be crazy, but I have seen very few providers who would turn down an extended date like you propose, and most would offer a discount! The bigger issue to me would be to find someone I get along with enough to spend that much time together! I can spend an hour with a hot provider who is annoying, but I’d rather not spend 12 hours with her! The question is how do you screen a provider for a 12 hour date if you haven’t seen her? Maybe short Zoom call first, or 1 hour meet the first day before committing to long session?

This is a real question… and I’ve thought as someone mentioned, that I should meet them for a regular ‘date’ first. You could be right, and what is ‘fun’ for 2 hours turns into a chore for 24.  

A trip to Chicago and an evening meal with a woman might be an investment well thought. If she isn’t compatible and it doesn’t seem like she would fit my purpose, then I can try again. Maybe make a weekend of it and ‘interview’ 3-4 women then decide.

Curious what did you say in your email that turned the company against you? Why would you bring up sex, etc when all you were looking for is a  legit tour guide?

What about reaching out to them again from a different email address and sticking to the tourist story?

I didn’t bring up sex.  

I said I wanted to hire her to take me on an all day tour, where she makes the plans in order to show me places I could then take a date.  

I was up front, too upfront I guess.  

This was the guides reply, before the company stepped in:

Do you have a set date that you will be in Chicago?
I will be out of town from the 28th through May 4th.
We can certainly plan an itinerary that’ll help you discover what Chicago has to offer outside of the Magnificent Mile. I can show you anything from posh locales to dive bars. There are many museums here as well…the best for a date are smaller, more intimate ones that won’t take an entire day to explore. We will also check out some of the best places to view the Chicago skyline..from rooftop bars to the edge of Lake Michigan.
Chicago is a multifaceted town, and we’ll explore its various offerings. After the tour, You’ll be prepared to impress any of your future dates.
The tour will last from 10-12 hours

This is the company’s response, after the guide:

Thank you for taking the time to reach out to the guides.

We became aware of your email because ToursByLocals retains copies of all communication between our travelers and guides, for quality assurance purposes.

ToursByLocals exists to connect travelers with independent guides worldwide for the purposes of experiencing unique touristic private tours.

After reviewing your message we are in a good position to confirm this is not the type of inquiry the guides on our platform would be able to assist with. Our platform is not the right fit for your needs, we kindly ask you to please refrain from contacting more guides with this request.

Thank you for your understanding.

And I’ve thought about reaching out to her, with a simple tour request. Her response told me she was into the idea. But I thought about an escort, and have been evaluating that route as an alternative.

if you are saying sex is not needed as part of the service.

 
https://rentafriend.com/

 
I suspect you can find a nice lady in Chicago that will be able to meet your criteria and do so at a much lower rate.

All you have to do is find a reputable independent contractor contact them and explain your situation. I guarantee you she will gladly help you out.

I'm glad someone here asked you the same question I had.  When I read your original post, I found that sentence vague (the reference you made to your email was without context or explanation). Thank you for clarifying by showing what was in it and the responses to it.

It appears to me that the company was worried their guide might end up in the trunk of a car or a 55-gallon drum or shallow demise or some other such unfortunate end. I doubt it's the first time they had to turn down business due to the Spidey Sense tingling.  

I am NOT accusing you of anything nor do I think you have bad intentions. I just see why your communication made them wary.

Please check you PMs, assuming you have access via VIP. Also, have you posted to the Chicago Regional board. Seems to me you should solicit the local board for this line of inquiry.

-- Modified on 5/22/2022 6:03:49 PM

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Yeah, you WOULD do that, wouldn't you.  I guess that's why noone would ever contact you for such an arrangement.  

Your a hateful racist angry bitch and clearly have no respect for any man alive.  And it shows with every word you type.

Goddamn your posts make me miss my ex. I do love me some toxic women.