I see her frequently. However,she is a friend and we are

closer than most family members(that's a given). That is the relationship we have agreed to have. So BE DAMNED those pundits of 'separation'.

and are CERTAIN that she will welcome your approach (and very few ladies would), treat her as you would any other stranger you encounter.  IOW, the correct answer is almost always to simply ignore her, and hope she has the same courtesy.

She is a woman that you pay for sex.  By nature of her occupation she leads a double life.  Don't approach her.

If she is in a situation where she is by herself, like shopping at a Walmart, then you could say hello if you feel comfortable.

If she is with other people socially, then I would let it pass.

Instead just pull out your wiener and dangle it back and forth a few times so she'll recognize you.

It's the discreet way of saying hello.

However, if you're on friendly terms and want to say hi, you can send her an email later on. "Hey, was that you in aisle 3 searching desperately for pumpkin? Sorry I took the last can!"

If you see a lady in public that you recognize from private time or this site, IGNORE her!!  You don't know who she is with or who she knows that is around.  Would be kind of awkward if a lady was with a family member and you came up and said hello.  Now how hard would it be for her to explain who you were?

Or if she were with her significant other.  How selfish would you be to say hello to her and strike up a conversation.  How would you feel if a lady saw you at dinner and she came over and said hello and your wife had just came back from the restroom.

Never say anything to anyone from this hobby in public unless previously given permission.  It can be very awkward and unwanted.  Maybe send her a note later asking if that was her you saw.

Living in Manhattan, you are bound to walk into clients every now and then. If I am alone, I let them take the lead. If I am not alone, I look away.

I never approach, but I have had clients see me on the street and smile and come give a hug or just a handshake. It is awkard only if you let it be.

Remember, what is done behind close doors is suppose to be between you and her, your choice if you say hello in public. I would not get offended if you didn't say hello. Here in the city, its so crowded on streets, you never know if your boss's wife is walking across the street and sees you ..

But thats me

Please don't approach me...

I was with a good friend at the mall and a client approached me. I smiled at him and turned around. He went right up to me to start talking. I was polite and my friend asked me later, "That guy is like twice your age, how the heck do you know him?" I said he was a family friend.

I really respect keeping my clients information discreet, I expect the same. A warm smile is always fine, but most my civvie friends aren't over 30 I'm not trying to be rude, but a big part of this "hobby" is based on secrecy.