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Writer's pictureThe Sue in the City

Naked Cowboy - Part 1



Every Fall my friends and I love going to a Notre Dame football game. The tailgate and atmosphere are very fun and a target rich environment if you know what I mean..


This year we decide to not even go to the game, just hang out at a local bar. While at this bar, this Cowboy keeps trying to come over and talk to me.


When I say Cowboy, I mean full-fledged cowboy with the flannel shirt and cowboy boots. I was with my friends and wasn’t really in the mood to deal with him, so I kept telling him to take his SH** kickers and giddy up on over to someone else because I was a city girl.


This made him follow me even more. He kept saying he doesn’t understand what that means to be a city girl and of course I was saying if you have to ask.

Anyway, he grew up in Wyoming, lives in South Dakota and was on a project in Ohio. He just drove to South Bend by himself for something fun to do while traveling.


He told me he had never been to Chicago and could he visit and take me out to dinner? He wanted to know my favorite restaurant in Chicago. I told him Gibson’s and if he could remember that restaurant name, I would go. He said game on.


I asked him if that Cowboy Hat would be making an appearance in Chicago? He said, it goes everywhere I go. Funny, I gave him my card and was on my way.


That week he emailed me and wanted to know what date would work for me for Gibson’s? I thought, impressive. He remembered everything.


We land on a Friday night to go out. Now, being in the hotel business, I was thinking the next question would be could I help him with a room or where to park the pick-up truck. Nope, didn’t even bring any of that up. He told me our reservations were made for 5:30pm on a Friday night at Gibson’s. Since I didn’t really know him, I wanted to meet him there and he said that was fine. He totally took charge of setting up the date on his own, I love it. Giddy up.


As I walk towards the restaurant, I see a giant Cowboy Hat in the window. Yup, he has arrived in the big city. I walk to his table and he has already met every table around us (which I love). Our table mates already knew my name and were very happy I was going out with the Cowboy. Also, I didn’t realize he drove 6 hours for the date and arrived early. Awww.


When the waitress stops over, he told me he wanted to be sure that I could order whatever I wanted as he was excited to have a great meal with me. When the bread basket arrived, I see him immediately start buttering the bread and putting it on my plate. I am sure I looked a bit confused, but it was completely natural for him to take care of me that way. Cowboys butter the bread for their date. Southern charm at its finest.


As we start talking, he asked me what kind of motels I sell for. Uh oh, I said well, first, they are hotels, but, didn't go into too much more detail. He is very inquisitive with me and said he really feels we should explore what we have because he feels a definite connection with me and a reason we met. So sweet.


He then asked if I would go with him to the Cubs game the next day. I didn’t have any plans, so I said of course, sounds like fun.


Fast forward until the end of dinner, we had quite a bit of food left over, and he told me he wanted to take it to go because he can’t let things go to waste. This brings up an interesting topic. I said, what motel are you staying at tonight that has a refrigerator? He said, oh no, I am staying in my pick-up truck tonight. HUH?


I said, why are you staying in your truck? He said, the MO-tels around here are expensive. I once had a co-worker pay $179.00 a night! I said, that sounds like a great deal for Chicago!


The bill comes and it was a couple hundred dollars (including a great bottle of wine) and I asked if I could help with it. Absolutely not was his answer.


I am sitting there thinking, he will drop money on a great dinner but will stay in his truck? What is up with that?


As we leave dinner, he finds a homeless guy to give our leftovers to, he is very sweet and caring. I like it.


We then move on to one of my favorite places, Ditka’s. There is a singer upstairs who sings old school songs and creates a great, warm environment.


Upstairs, we sit at the bar and order a beer. A couple proceeds to sit next to us and we start a conversation. No sooner does that happen when my cowboy decides he wants to buy them a drink. He definitely is not cheap, just won’t spend his money on a motel room.


Then, you guessed it, we are two stepping to songs that you would generally not two step to. We didn’t even care and he was a great lead while dancing.


Then the singer belts out the star-spangled banner. My cowboy immediately stood up and took his hat off to pay his respect to the song. These cowboys are patriotic!


We have a great time, and it is close to time to go home. Since he had never been to Chicago before, he asked me if we could walk down Michigan Avenue, I said sure.


We decide to go for one more night cap to a place right by my house. We walk in and this table screams, Cowboy, sit over here! So, we go over to this table and of course they are a couple from Texas. My cowboy immediately goes over and buys them a drink for their thoughtfulness.


As we are sitting there, the wife of this couple leans over and asks me how long we have been married. I laughed and said, this is our first date. She didn’t believe it. And, I said, does he seem like a serial killer? She said, absolutely not, he seems like a stand-up guy.


Lesson Learned? When a Cowboy visits the big city, he definitely gets attention everywhere he goes. Especially from people who may also be Southerners. I very much enjoyed the kinship he developed with random people due to his charm. But, do opposites attract? Stay tuned for the conclusion next week!


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