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.

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One Response to Hotel Bar Woman

  1. NoAmbition says:

    Very interesting … maybe she just wanted to hang out some more and have a drink or two, though if that was the case she should’ve said something to you like, “I’m enjoying talking with you and thought we could continue talking over some drinks.” But, of course, there’s some assumption among many (most?) women that the man has to initiate everything … drives me crazy.

    The point of your whole TTS effort/blog is, in essence, to be more communicative. I know most people don’t have this ability (i.e., to talk more than they’re used to), but after spending 90+ pleasant minutes with this woman one would think she’d feel comfortable enough with you to tell you what she’s thinking. Even if she wanted to sleep with you but didn’t want to admit it, she could’ve just said that she wanted to hang out some more.

    I don’t fully understand why you ran, but if that was your gut reaction (and we could spend years pscyhoanalyzing the decision … you subconsciously love Chloe, you feel like you’re too old for hook-ups, whatever) it was right to follow it.

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