I'm getting signals from a VERY gorgeous 30-ish single woman/no kids that she may be a discreet provider.  At least I THINK she's giving me signals -- or am I interpreting them from a hobbying perspective?  I'd hate to make a mistake, since this woman is fairly known in my community/circle (as am I).  Fact is, she's a real trophy score, lusted after by every man I know, so it's worth a try. I'd sure appreciate the group's take on the signs I'm getting, and any tips on how to discreetly broach the topic with her.  We're having lunch on Friday.

The woman, we'll call her Joy, is the former teachers assistant at my kid's school, which is how I got to know her. She left the school, bounced around some odd jobs and we've chatted on the phone off and on.  Joy's now going back to school and is apparently desperate to earn some coin; she keeps calling me to ask for a part time job. But then last week, her tone changed in some emails we exchanged. She stopped asking me for work.  Instead, she wants ideas of how she can make money. She can't find any job, she says, because her school schedule only makes her available late afternoons and evenings.  She's tried everything.  She wants to brainstorm with me, she says, on how she can make $300-$400 a week, to see if I have any creative ideas.  I write back that paying $350 a week is nothing for me, and I'd love to help out.  She's back to me in a flash and wants to do lunch right away.  I call her up, we chat, Joy says she even explored jobs as a "personal assistant", but those jobs require too much time. She mentions again she wants to brainstorm and get creative about what she can do to make $300-$400. One other "sign" -- I've seen her around town a few times being pretty cozy with men 20 years her senior.

So, gents and ladies, what do you think?  A flakey girl or part-time closet escort?  And an even bigger question: How to feel her out and broach of subject of doing escort work?  Anyone have any experience turning civilians on to the profession?  Any thoughts will be much appreciated.

You leave out a key piece of information:  Would this woman consider you a friend?  It sounds like she's in dire straits money-wise and maybe she's only looking for a magic idea that will solve her problem.  Is she naive? I don't buy that she can't find a job, though.  If she's THAT attractive, she can always get a waitress or hostess gig.  Sounds like a part-time/first-time provider.

To answer your question, no I wouldn't consider her a friend.  An acquaintance, yes.  I don't think I've had a conversation with her that's lasted more than 5 minutes ever.  So it's not like I'm her designated shoulder to cry on.  Hardly.  She's always impressed me as a pretty tough, worldly woman.

Give her the idea of discreet escorting, perhaps she'll buy into it.  She does not need to do it full time, explain the good amount of $$$$ to be had if she decided to do it. An easy way to make some serious bucks!

You might want to try the "massage" angle.  Tell her you are pretty stressed from work lately  and/or hurt your back lifting some furniture.  Maybe you could ask her subtly if she has any "therapeutic skills" and see where it goes from there.

Sorry, that's all I can think of for now.

Well, it's hard to tell in these cases....She could very well be open to such things, but on the other hand; you could suggest it to you and she slap you across the face with her mouth agap ...furious you'd ask her such a thing... So this is what I'd do:

Tell her you had a friend (the friend thing is always a good idea) who had a few wealthy suitors who paid her bills and she kind of dated them a few times a week or something like that... say you aren't suggesting that you and she do that or even if she do that, but it's one way to make quick money. You could give a casual laugh at the end of your story.

If she says right away "I would never do that! I've dated a few older guys but I'd never ever consider that --then you know to stop there... If she says "yes I've done that or yes, I'd be open to that ---THEN (and only then) you could suggest something more between the two of you.. .and say you wouldn't even suggest it but SINCE she's open to it... and go from there.

Just my two cents...

Good luck

A

I THINK YOU HIT THE NAIL ON THE HEAD. SHE , LIKE YOU, IS LOOKING FOR A WAY TO BROCH A DIFFICULT SUBJECT. TELL HER YOU HAVE AN IDEA ON HOW TO HELP HER OUT.AND IDEA THAT WOULD BENNIFIT BOTH OF YOU. iS SHE INTERESTED IN GIVING UP TWO HOURS FOR A DAYS PAY? BY THIS TIME SHE'LL FIGURE IT OUT AND GIVE YOU A + OR_ SIGH. YOU CAN ALWAYS SAY YOU WE'RE ONLY THINKINF  OF HER AND, AN EASY AND JOYFUL WAY OUT OF HER PROBLEM.

Keep us posted...this sounds interesting and promising!

First of all, do not ask any direct question, not yet. There are more diplomatic methods of achieving the same objective.  Act more seasoned.

I assume you are married ... go out with her, tell her you would like to help her a little.  During the course of dinner, movie, sailing, whatever other activity you try to conjure up, you will have the opportunity to accidently "touch" her, or "goodbye kiss", or something like that.  At that moment, she will either respond with passion, or not.  If she did, you could then define the boundaries, and rules, and part of the arrangement will be the financial part.

The complexity of this situation is you would not have the flexibility and freedom of having the same thing with a provider.

If she is a "babe", very good looking, then it may worth the risk.  My difficulty in these situations have always been at the end of the interlude, getting asked "when am I going to see you again?"  and I am not even that good in bed!

don't force it, but be open to her signals. Let her make the move.

The fact she jumped at the chance to "talk about it" leads me to believe she's game. I'd throw something at her jokingly, but in a way that if she's game, she'll get it.

...this woman saying she wants to brainstorm with me to find ideas to make money.  It's not like she's asking me for a job, or asking me to make contacts for her.  I told her we're on the same page and that this could be a good thing for both of us (hint, hint) and her reaction was to accelerate lunch from someday to Friday.

You could sort of jokingly suggest it...

Her: "How can I make 300-400?"

You: "Well, you could always try being an escort."

If it's said in the right way I don't think she'd be offended, and if it strikes a chord then it gives her an opening. (Figuratively speaking, of course)

-- Modified on 1/28/2003 7:50:07 PM

Be direct without being crude.  I recently received a phone call from one of my former students who is now in nursing school.  She mentioned that money was really tight and she was wondering how she was going to pay her car insurance.  I suggested that we get together and "have some fun" and in return, I would pay her car insurance premium.  She nearly jumped out of the phone to thank me for suggesting it.  (She was hoping that would be my suggestion, but was too shy to suggest it herself.)  We now get together one a week or so, and have some great sex.  Another bonus:  because she is not a "pro", I see her for 2-3 hours for less than $150 a pop.  Not bad at all.

Me: Done, How soon can you start?

You said she was amenable to getting together to "brainstorm" with you.  Well I suggest a working lunch "brainstorming" session.  Take her to lunch, and ask her specifically what jobs she's considered and rejected, and why they were rejected.  You can mention escorting but ONLY with a tongue in cheek or humorous attitude, and in combination with and at the end of a short list of some other suggestions.  Not like you seriously mean it, but more like you are trying to rack your brain to help her out.  With a silent pause afterwards, look for any kind of response, verbal or otherwise.  If none comes your way, say that you were only brainstorming, and quickly move on to another subject.  If she does respond with a non-verbal but positive gesture, like a smirk or smile on her face, simply ask, "What are you thinking?"  You can always apologize if in some way you offended her, so long as the way you broached the topic was somewhat humorous.

Good luck, and keep this board posted on the results.  You know what kind of guys we are when it comes to stuff like this.

F.

Hay mayor so when are you going to turn us boys on to this new student you found??

or whether I'm just viewing them through the myoptic eye of the hobby.  The guys have weighed in, but they're all hobbyists, too.  What do you think?  Does this woman's situation sound like one conducive to going into the profession?  You all went from civilian life into the corps.  Does it seem likely she's doing the same?  Opinions, anyone?

I think you have had some generally good responses. I agree that the casually joking thing will work. I also think you will be able to tell by her eye contact with you and reading her eyes. Understand, that she will be reading your body language to see how you are handling this and your reaction to her aggressiveness. Personally, I think this may not be her first time. If you say you have seen her out with gentlemen 20 years her senior, that is a tell tale sign to me.  You didn't say where you have seen her but I would guess it wasn't at Waffle House..Sooo, think about that. I applaud you for reaching out and doing so in a repsectful manner and the responses have been very considerate and thought out for the most part! BRAVO gentlemen.

I am going to bet that you will know within the first few minutes. If she is asking you for $300-$400 a week, and not 100-200, she knows what she is doing. Oh, this remindes me... this is a warning!!! Don't get taken by what could be potentially a bad situation. If she is not someone you can trust, to a LARGE degree, don't do it. Honey, I know you are interested, hell I am interested in the result, but don't do something or suggest anything between you two unless you really feel good about it. You have alot more to lose than she does...

We professionals, for the most part, do this and survive because we are discreet, trusting, and you know what you are going to get per se... If she isn't totally cool and mature enough to handle this, I say give her a few suggestions and leave it at that. Don't let the thrill of this keep you from thinking clearly!

I hope this helps or is something for you to consider.

xoxo
As always, think naughty thoughts
Brooke

-- Modified on 1/29/2003 1:50:30 AM

It sounds like you are in the lower Hudson Valley (RCNY).  If she sounds interested, suggest escorts.com.  I would be interested in someone that age, etc..

MAYORQUIMBY,

If she goes for her masters give me a call . A mind is a terrible thing to waste.

See her for lunch. When you are chatting, gently put your hand on her hand or bare arm on top of the table. Her body language will either pull away of soften. If she softens, maintain physical contact. If she touches you back, there is actual interest, professional or not.

Make a joke about someone you've met working the Chicken Ranch. If she bites, bring up that LA is the porn capital of the world and maybe you and her can act out a professional fantasy. If she bites, look her straight in the eye and tell her right now you are so attracted to her you could explode. Ask her to go with you right now. Alrready prepared, have an envelopem with $300, room, a condom or two and perhaps some wine set up. If she goes with you you are probably going to get laid. Ride the wave until the white water shallows! BUT if at some point she changes her mind, let her out! Or if she doesn't bite, go thru with a casual lunch, hug her and tell her good luck.

If the ride goes all the way to completion, get completely dressed, while fawning over her. The on the way out offer her the envelope as a gift, a token of appreciation.

Have fun.

I agree using tongue in cheek about escorting is a good way to see if she is game. You can mention it when discussing what she wants to do with how much she wants to make. If you are going through a list, then just say something to the effect "hey, we left out escorting" :P If she laughs and makes a cute remark, then slowly ease into a conversation about it. If she's like, I don't think so, well, you've got your answer.

BTW, if she is game and in NYC or NY region, let us hobbyists know.

"Wow, you look terrific. I've been thinking about your dilemma, and it's really hard. (Slight laughing) I haven't come up with too many good ideas other than becoming an escort, (chuckle) and I doubt that's what you had in mind". We all know where this is going if you only have the guts to take the chance. Nobody wastes their time with you if it's not worth their while.

Lot's of good advice out there dude.  I'd say that you want to be a really keen observer on this one.  The potential for a faux pas is very high.

Observe what she wears, her hair, her make-up, her body language. Watch for flirting/sexually open signals.

Also watch to see if she is obviously nervous, like looking around, fidgeting, drumming her fingers or stroking the wine glass and while she is looking away from you.

Consider also your interactions with her in the past.  Has she been brushing up against you or touching your clothing, wetting her lips when you talk to her. There are a lot of things to observe, but it sounds like she may be looking for you to be her sugar daddy.  The 300-400 dollars a week could be a sounding board or a number she pulled out of the air, but I don't think so.

Proceed with cautious optimism, and let her lead the conversation for a bit to see where it goes.  You can move any conversation in the direction of sex at any time with very little effort.  See if she takes you there first.

Also ask her what she really wants to do with her life, where does she see herself in 5 years.  I like running my potential significant others past my hunting dog.  If he goes over to them and cozies up to them he likes them, if not, he's completely aloof.  It's been my experience that he's right on the money every time.  Don't know if you have that luxury, but if you do, what the Hell, give it a whirl.

HPG

You know the one thing that you have going for you is the fact that she said "brainstorm" with you.  That term means that you are just throwing out ideas without any judgement as to the validity or feesibility of it.  So, with that in mind, you might mention some other options that you KNOW she will not go for, then mention the option of part time escorting or massages.  If you mention that brainstorming is just throwing out ideas in the beginning, then there shouldn't be too many issues with her reactions.  Good luck and keep us posted!

joercny,

PLEASE ... get back in the cold pool!  See my earlier advice:

"First of all, do not ask any direct question, not yet. There are more diplomatic methods of achieving the same objective.  Act more seasoned"

You effectively asked her to prostitute herself by giving that example.  If this lady was comfortable with that, would be getting into the business directly ...

See her soon, hold her, kiss her, treat her with love, respect and dignity, she will respond!  I bet you a penny!  you have come too far to back down now.  Don't lose your nerves!  This is what life is all about, conquests!!!  This is now more than just sex, this the "hunt", the "chase", something we all live for!