I have a client that I really enjoy. He is single, young, smart but extremely shy. We have had so much fun together. We have met each others friends and family. We talk almost daily, he understands me and I him. I have hinted that if he asked I would pursue more. He has been to shy to take the hint. Should I just ask? I no longer receive reference requests about him. I don't want to lose a good client and more importantly a friend. He is not rich, I don't want to be supported anyway but it means I would need to continue to work if we were to date and my financial goals met. Is this a bad idea?

..I have no experience in this situation. Hopefully Mr Fisher will respond.

Funny I am kind of going through a similar thing though from the other side of the coin. I personally don't see any reason not to ask but it could be in the way you do it. You might want to preface the conversation with something to the tune of letting him know there is something you have had on your mind for a while and wanted to get his take on it. Be sure to say there is no pressure and point out the obvious things that you both get along so well and seem to really click. Just ask if he would be interested in spending more time together just see how things develop. If he is hesitant then ask what reservations he may have. Don't be forceful as some guys just can't say what is in their head all the time (believe me I know, I'm one of them and trying to work on it). If he just seems like he can't discuss it right then remind him there is no pressure and let him know you are open to talk about it at any time. You may get your answer or you may not but at least you will have tried.  

We are guys. You have to be straightforward with us. I've had civi girls tell me I "had my chance" and all I could do was "when? Was I there?" We don't pick up on things and in hobby land we are extra careful that we don't cross any boundaries.  
You are going to have to be very forward and leave nothing up to question.  

Sounds like you two enjoy each others company outside the hobby so I'd say give it a shot. If both are in agreement. He may be shy but he wasn't to shy to visit an escort. I also look forward to Mr.Fisher's input on this as well.

Just sayin

...I dated a lot and I'm one of those shy guys as well. The way I intepret this is that he's shy cuz he thinks you are too good for him, you are probably on a pedestal. What my aunt (ex-hooker) did was she started to offer her 2nd husband (when they were not married yet and still hobbying) more and more OTC time. This OTC should be revolved around activities which gives him confidence like something he's good at. In my aunts case her second husband was good at cooking so the otc was revolved around cooking dinner together at her place. They eventually started dating. The goal is to raise his confidence. She transitioned out of sex work though into legit business.

I would just ask the client if he wants to date. Regret is a hard companion to live with so I would just go for it. It sounds like you both like each other.

...the moment you stop collecting his donation is when you start dating. If you must stay in this line of work for economical reasons, he will have reservations about sharing you with other guys; just bring a girlfriend from time to time for threesome action and see how you can handle seeing him with another girl. If you're cool with that, then you'll have an argument for him to also be cool about it.

I have seen many but nobody I have ever
wanted to see / date OTC.

but since there were already so many responses I thought I'd read them all first, Surprisingly enough, yours was the best. kudos IMO, you nailed it.

To the OP:  There are many good arguments to go either way.  Roll the dice.  I did, and don't regret it.

My answer was hardly about me, my reference to my own LTR's with escorts was purely offhand and for context.  

Most guys understand that the escort is supposed to be friendly and make us feel special. I wouldn't in a million years suspect an escorts interest in me was more than business as usual, unless it was spelled out to me.

need to constantly criticize others?

I was a huge fan of In Sides.  
Orbital + getting high = a great time.

Hey! I'm NYC!

I say go for it. if you're the only girl he is seeing he definitely likes you.  Do you know his past history why he was searching for escorts in the first place maybe something happened to bring him to this world.  Not everyone's looking to sleep with hundreds of people I'm sure there's more to the story. Take it slow and have fun.  I hope all your dreams come true and it works out

these two women sat next to me and my date. They sounded so judgmental (i dont generalize it to everyone in NYC, but these two were definitely quite the pair of B-atches), they sounded so condescending to each other. Made me wonder if living in NYC makes you become that way. Anyways. I would say people anywhere can be full of themselves. You just see more of them in NYC cuz there more douche bags per capita there lol :P

Dropping hints, is a stupid way of going about getting something you want. I would imagine he isn't paying you while you meet each others friends and family, and if he is. The hints you are dropping aren't obvious enough.  

Imagine if  every "hint" that a lady dropped during a session, was misconstrued as hint that she is actually into the guy?

... I'm not from NY, and I criticize everything.

With the arrogance, I know everything but can't prove it BS and nothing to back it up...in my experience that is...lol...wouldn't want to throw them ALL under the yellow bus.

-- Modified on 12/5/2015 8:54:31 AM

EVERYONE I have met or had any interaction with, from NYC and those other two areas as been  a douche bag....and some of the women too.

that LTR's with providers happen...a lot more then most might think.  
How it goes depends on what each wants for the really long run and yes.

The regret you might feel NOT asking is not worth it. You have a 50/50 chance of the right answer. If you don't ask, you have a 100% no.  

...go into this with your eyes wide open.  The potential for love/romance/real intimacy often obscures the risks for hurt and disappointment.

...so the yellow bus is safe, for now...

meet him off the clock somewhere and see what happens next.
Don't listen to anyone who says it will end badly or it can't work.
See what happens and don't expect more than he can give.

The money is too good to just "leave"
And while many guys say that they are OK with their GF providing ... That does not last long. GFE providers are skilled in providing the perfect GF, but IRL that girl doesn't exist.

i had similar situations before
shy guys are hard to date, they are usually quite and you don't know what is going through their mind and what they like and what they do not like, you have to sense it

Haha I see ur attempt to demonize me on the board as the "women hater tranny"... Not gonna work. Now you... I think people already figured you're the troll of the board. At least one of them.  

You forgot Rhode Island.  

You mean they aren't. Now, you had to ruin it for me didn't you?

I see somebody has been watching Dr. Phil a great deal...

Aren't you the guy who dumped  the  "love of your life"  because she fucked a bar keep  in the back room ?  
   
  If you aren't willing to give the " love of your life" another chance because of her actions one drunken night, you  certainly are not  mature enough to date a provider.  
   You took your GF's  actions too personal when it was not about you at all.  
   
 I'm not saying you should have asked her to douche and have sex with her the same night.  
   Giving her a time out for a  month, two, or perhaps a year would have been a more appropriate response if she was truly the "love of your life".  
   
   IMO you have no clue of the true meaning of love.  
   
 P.S.  If you mature, it's possible you could reignite the flames you found with the "love of your  
   life"  
 You might find, make up sex is often the best that can be found or rented.  
   
   If you called her a whore your chance of reconciliation and her looking at you as the love of her life, are slimmer than none.

I was pointigon out the behavior that you claim to have displayed on the train.  
 

Everyone forgets Rhode Island!  

But I shall take your word on it.

There has to be a few of you at the very least.

...in the Hudson valley...I try to not be an asshole...sometimes I succeed...

I think you have already crossed the line into friendship.  If you are both available, then continue down the road.   You'll need to be plain about taking it to the next level but at the same time...   It'e ok to say you don't have all the answers or know where this is or can go...  the joy is in the discovery.  
Best Wishes.

etween the New Yawkers and Massholes ... They never stood a chance.  

I think she would say, "Love is for suckers!"

I think narcissistic is French for Asshole.

You must be right!

I am wondering how many hobbyist are thinking this "post" is about him? LOL

Do not miss the chance to find that one special person. I did not and have regretted.

you were actually speaking about each other?

Are the ones who manipulate a Provider in thinking there is chemistry that may lead to potential personal intimacy and a relationship JUST so they don't have to pay.

I envied him to see Weezer with me in a few days because he loves classic rock. I will spring it on him after. The advice about deemphasizing sex is a great idea. If he's up for it I will suggest we take a month or two break and get to know each other without sex.  

I know other providers who have tried it.

Oh, how I wish but I can assure you this is not the case...