While waiting in the lobby of a nice hotel, waiting for my date to get ready, I noticed a beautiful woman alone with a few small bags.  

She was obviously dressing down her hotness with baggy casual clothes and shades. She might have just been a tourist, but there was something about her that made me think she wasn't.  

Is there any way to inquire about a woman's possible involvement in the hobby without sounding like an ass?

Ladies, I'd love to hear your thoughts.

If you are going to approach a woman, do it as if she were a civie you are trying to chat up.  If she's in the biz, I am sure she will figure out how to inform you.  If she's just a civie, you might get free sex.

How many times have you hit on a girl only to get “$1000/hr” in response?  Same shit, I would think.

if she allows it, then smile.  If she smiles back, go over and say hello.

 
I think you can take it from there.

But the last time I hit on a girl in Vegas, that is EXACTLY what she told me "$1,000 hr" to which I countered $500 and within about ten minutes we were fucking our brains out.

 
For the record, I do not recomend that ANYONE else do this, and just to assure everyone that I have not lost my mind. I met her right by the elevators, we went right up to my room and before I kissed her or had even a sip of water EVERYTHING I had of value was immediately deposited into my room safe, besides a single purple chip which I gave to her AFTER she got done fucking my brains out. Ironically, I saw her a couple of times afterwards and every time she still tried to hit me u for a grand and every time I had to remind her I was only willing to part with $500.

 
As for approaching a girl you think "might" be a hooker, I completely agree with SH, I would chat her up like any other civvie, if she's a pro she'll let you know in short order and if she's not a pro you won't have blown your chances by accusing her of being a hooker.

Thank you so much for your reply Heather. I can certainly see why both of those advances would have made you very uncomfortable.  

Would it have been different if the man in the restaurant greeted and spoke to you as if you were a civvie? If he asked for your number, would you give him one? Can you imagine a conversation that would lead you to bed with a man who saw you in a restaurant, but didn't recognize you? I don't mean a civvie hookup, I'm talking about a paid encounter.

and just like doctors, lawyers or accountants they are not always on the make for new clients.

 
Let's say you recognized a woman checking in at a hotel who you thought you recognized as a doctor, would you go up to her and ask for an appointment while she was obviously engaged in her private life? The same thing goes for sex workers, here is my rule of thumb, if I don't know her well enough to know her REAL name, I keep walking. That is unless its a social environment where I would not feel out of line approaching her as a NON hooker.

I couldn't agree more. Civvie is seeming like the only respectful means of approach possible.  

If not for this particular woman's je ne sais quoi, location, and feeling like I may have missed an opportunity to make a new friend, I wouldn't be searching for a technique.

No!

You would seem like and be an ass.  

And if she is a provider, you might be outing her to the hotel staff.

Even if she is, she would not appreciated being treated like a streetwalker, which is what this would amount to.

If you had a chance with her in her normal approach to advertising, you would have blown it by your approach. They really appreciate discretion too.

A bit of glancing flirtation is okay, but only if she seems interested in you. Otherwise, leave her to your fantasies.