Road Trip to Chicago

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Best bar - Bootleggers was a lot of fun as there was a bachelorette party going on and the gals were wonderful to us.  We danced with them for about an hour and then moved on to another club called Syn.   Syn had a disco type atmosphere with couches and coffee tables dark with flashing lights and techno music.  Several guys talked with us there.  One husky guy, a former boxer, was very inquisitive and friendly.  Always good to have a boxer on your side.

      Sharon DeWitt in Chicago     


Most memorable dance.  Syn I went out to dance and all of a sudden, a stranger appeared in front of me and extended his hands.  I reached out and we began to dance. His manor of dress was very unusual.   He had on a high-buttoned black vest, black pants and white shirt buttoned at the collar.  His glass frames were dark and very plain.  He wasn't very tall and reminded me of someone from a very plane religious sect.  He led beautifully and though it was to the beat of the music, the dance seemed very slow and flowing with graceful moves, almost a cross between a Victorian type of dance and swing.  He never said a word as we performed our intricate patterns and went the song ended he just slipped away and disappeared.   I had hoped he would be there the second evening, but he never returned.

Most memorable dinner.  Our first night we went out for dinner at Gibsons.  We arrived at 7:30 and was told the earliest we could be seated was 9, they told us we could wait in the bar and maybe get dinner in there, so we entered the bar area looked for a table.   The bar was absolutely packed and of course, there were no tables.  We did get several looks, but no one said anything to us.  I was a bit nervous and I think Lisa was a bit more nervous.  We were there and to turn around would seem like we were running plus we would just have to do the same thing somewhere else.  We made it to the end of the bar and saw no tables around the corner.   A waitress asked us if we would like a drink and we ordered and asked if she would keep an eye out for a table for us.  While we were enjoying our drinks a couple of tables vacated and were reoccupied so when we spotted a guy sitting by himself and asking for his check  I went over and asked if I could sit down.  He sad sure he was about to leave and we claimed our table.  The dinner was excellent and as we were finishing a gal approached us and started a conversation.  So there were five of us each other's company.  We exchanged cards and Lisa and I departed for an evening of clubbing.  Before leaving we did make a stop in the ladies room with no problems or questions.


Best friendship in Chicago.  We had dinner at Rupert's at the Hyatt.  Downstairs was a nightclub called The Living Room.  The dinner was excellent and the décor was plush.  We finished dinner fairly early, just a bit after nine, and went downstairs to get a table.  People were just starting to trickle in.  By 9:50 there were several people there but no one was dancing.  I told Lisa if no one started by 10 I was getting out. 10:05 a Cher song started so up we popped and headed for the dance floor.  Thirty seconds latter three couples joined us.  After some time had passed, a young lady came up to me and complimented me on my dress.  Latter three gals Debbie Lisa and Kelly joined us and started a conversation.  We spent the rest of the evening dancing and talking.  What a wonderful group.  Hope you gals can come to St. Louis sometime.


Best shopping - I shopped Michigan Ave during the day while downtown but my best shopping experience was in northern Chicago at Nordstrom's Rack.  There were shoes galore and lots of good deals on clothing.

Naughtiest moment.  The morning we left Chicago, I decided to wear a full pleated black skirt and red blouse.  While traveling between cities, we stopped for gas at a filling station and I went in to use the restroom.  Two truck drivers were talking with the cashier and when I left they followed me out.  As I approached the car, a gust of wind caught my skirt and sent it up like a full parachute.   The one truck driver exclaimed, “Whoa would you look at that.”  I turned around gave a coy smile as I hopped into the car.




     Hotel bathrooms with two gals sharing a room the bathroom can become a little crowded in the evening before going out.  It did take a bit longer to get ready.  We did manage without a problem, but it would be nice to have two sinks and more counter space.

     Packing for a trip - I pack too many shoes and dresses.  Pick out two or three pairs of favorite shoes for day and evening and work the rest of the clothing around that.  A simple black dress can be extended into several outfits with scarves and jackets as accessories.  Take clothing that doesn't show wrinkles.  Select only one or two favorite wigs.  Minimize the makeup by taking only what is necessary for one night look and one day look.  Leave all the extra items at home.

     Biggest disasters - I lost my black leather cap. Lisa's strap broke on her dress while we were miles from the hotel.  Luckily we were able to attach it to her bra strap.

     Best cab driver incident.  One evening we were considering going to a fetish bar, so we decided to put on our leather (leatherette) outfits. Lisa had on boots and I choose 5" black heels.  We went out the front door and the doorman flagged a cab.  The cabbie saw us, wiped the cab over and ran up on to the 6" curb.  The doorman chucked as he opened the door for us.


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