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 am 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, coffee house in Intercontinental Hotel. Perhaps go upstairs for an hour, 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 tryst. I want GFE for the date, as if she was truly my GF for the day.  

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.

-- Modified on 5/16/2022 5:54:32 PM