Hotel Bar Woman

This story doesn’t end how you think. I did not meet a lonely businesswoman in the hotel bar and wind up in bed with her.

I did, however, meet a lonely businesswoman who wanted to go to bed with me. At least I’m pretty sure she did.

After a long day of looking at incredibly boring documents, I went back to the hotel to change out of my suit. These trips used to be more fun when I was more junior because then a couple other associates would go with me and we’d go nuts each night trying to outdrink each other and pick up women. But now, I’m senior enough to go alone and at night, the last thing I want to do is party with the client.

So I went down to the bar to get a beer before ordering room service. That’s when I saw her. A woman in her late-thirties, sitting alone, reading on her iPad. I immediately had a time-warp sensation like it was 1977, or at least I was in some movie set in the 70’s. The way these things are supposed to go is I buy her a drink and ask her what her sign is.

That being the case, I was very hesitant to go up to her. It just all seemed a bit too… obvious. Like how could I seem authentic with no agenda when an entire body of literature says otherwise (thanks, Jackie Collins).

But I tried anyway. I said, “What are you reading?”

She looked up and studied me before answering, “Unbroken.”

I had no idea what that was so I just said, “You waiting for someone?”

She said, “Nope.”

I said, “Well, I’m here on business and I hate to eat alone. Want to join me?”

She looked at me again, trying to figure out if I was attempting to pick her up. I felt her stare and blurted out, “Just dinner.”

That made her smile and she said, “Sure.”

So I sat down and we talked. She is a corporate lawyer working on a debt restructuring. I actually found it interesting because I do similar work. We ate at the bar, talked for ninety minutes or so, and that was it.

At the end of the meal, I said, “Well, it was nice meeting you” and started to get up. Then she looked at me, kind of insulted, and “Wait, where are you going?”

It was suddenly awkward. I had said “just dinner,” hadn’t I? I got a little flustered and said, “I’ve got to go over these documents…” as if I had some papers with me, which I didn’t.

She looked hurt. Like, I had told all the necessary lies so that our tryst could seem innocent and now I was backing out of our tacit agreement. The whole thing got pretty weird.

So I just ran away.

Maybe I should have seen what might have happened. She was attractive and it’s not like me and Chloe are so far along that we’re monogamous (at least that’s my position). But I felt like I had gone into the situation by being honestly Platonic and that if I somehow changed my mind then I’d be making myself into a liar. Or something like that.


I am in Chicago. Sometimes I have to go to stupid places like Chicago on business so I can do due diligence. Whatever.

Here’s what I decided to do on the plane. I challenged myself to talk to the person next to me, no matter who it was, for more than a couple minutes. But, I had to do so in a non-annoying way so the person didn’t that I was that guy who won’t shut up. In other words, I had to get the person next to me to do most of the talking.

So as I got into my aisle seat, I eagerly awaited the person whom fate would deal me. Would it be a friendly old lady? Too easy. A hot blonde? Too tough. Nope. It was Middle-Aged Marine Guy.

MAMG didn’t actually serve in the Marines, he just looked like he did. You know the type. Crew cut of grey hair, muscular, tight polo shirt. At first I thought he was an air marshal but he when he opened his laptop and started working on the sales presentation for industrial pumps, I thought that was going a little too undercover for a marshal.

How to launch in? I couldn’t comment on what he was working on because he might have punched me in the throat for looking at his secret presentation. Weather? Too obvious.

Then it hit me. Chicago!

“Are you going away or coming home?” He was coming home.

“Oh, so maybe you can help me. I’ve only been to Chicago once before. Do you know any good places to eat? I really want to get some good pizza but I’m afraid of winding up at some tourist trap.”

And that’s really all it took. He had strong opinions about pizza. He told me where to get every kind of food I wanted and even said he could get me tickets to a baseball game.

MAMG has five kids and two grandkids, which is surprising because he doesn’t look that old. He’s the regional sales manager for an industrial pump manufacturer. He was never in the Marines, though he did play football at Notre Dame (not sure how that was related but that’s what he said).

Anyway, mission accomplished. We talked for about half the flight before he went back to work. I chalked it up as a victory.

Oh, and in case you were wondering, Tad is staying with Chloe while I’m gone.