scribble a note...

dont take him out one a "free" date

 
blur the lines...he gets happy thinking you want him
then clings
you fire him
you lose $ and client

If you feel it in your heart to do something nice for him. Who not? If we did things based on the possible consequences or repercussions of doing something good then no one would ever do any good deeds ever. I do understand however your concern, so it would be wise to make it clear you just wanna show him not everyone "sucks".  

If you feel like cheering him up a bit. DO IT 😘. Says a lot about you as a person IMO. And makes me automatically like you for being a kind hearted person. The opened up to you and that means you gained his trust 😉.  

Some people actually NEED to be used like this by family and friends to feel relevant, but then it makes them unhappy to think they only love him because he helps them. It's a vicious circle for some people. They are actually afraid to be happy, it's as if they are afraid to find out if their life would still suck even if they took away all their obstacles to being happy, because without a reason for their unhappiness, then what would they do?

As to your actual question, you always run the risk of being "taken the wrong way" when offering OTC time to a man who is paying to have sex with you. I wish I could make the call for you, but some guys will appreciate your gesture for what it is, others will hear wedding bells. None of us know enough about him, or your relationship with him to make this call for you. I would simply say "proceed with caution"

As providers, we meet men with all kinds of discontent, some more existential than others. In my own career, I've certainly provided a sympathetic ear and advice if it's requested. But I think the situation you describe is beyond the reach of a free dinner to cheer the fellow up.

And not to be cynical, but I also wonder if some people don't play the victim card in order to generate a sympathetic reaction exactly as you describe.

Personally, I'd continue to be yourself in your sessions, because that clearly entertains and satisfies your client while he's there... And honestly, I think that's about as far as our mission should take us

if you see him as a workplace friend and feel like he is a good dude, then do it.  You will
reap the good Karma.  Just tell him up front what you say in your post and it will be good.

Just be careful!

It's nice to hear providers caring about their clients.
Just be careful with this guy and test him out a little more.
 

but have you considered that he may have just needed to vent? He may not want to blur the lines of the personal/professional relationship. A large majority of what we do is taking on the emotional burdens of our clients. They tell us things they don't feel comfortable talking about with the people in their real life, because we aren't a part of it. He may want to keep you at a professional distance so that he never has to start thinking of you as someone he has any emotional responsibility for. Obviously you know him better than any of us, but I think it's a good idea to consider that he may need you to be a constant in his life as you are more than he needs a kind gesture. It may be a better idea just to do something special for him in one of your appointments, or have some sexy photos taken of you just for him, something like that. You can show him you care while maintaining a professional distance.

if it starts out as "people suck", that is unusual in my mind.    

Many people do thrive off of the  feeling that they are able to "help" others do better in life, and all that is needed is that they depend on and listen to"me".

I'm not at all saying that your friend is like that, but those kinds of people do exist and are very scary

My fear for you as well as your client is if you do something like this you are crossing a boundary. Not saying stepping outside the norm on occasion is necessarily bad. But it does have risk.

You do not know where this new path might lead. You don't really know the psychological make up of this individual. For you it is a nice gesture . For him it could have a totally different meaning......expectations.

I'd suggest going about it in a different way.
Perhaps a simple email letting him know you have been thinking about him. For example I had a little medical issue recently. One of my faves knew about it and sent me an email with a sweet real life pic of her encouging me to get better soon as she was waiting for me ! It actually meant a lot.

Perhaps instead of inviting him to meet for a surprise ( who knows what that might mean to him) you could suggest going out for a drink or bite to eat after your next session. Then insist on picking up the check. And make clear you are doing so because you want to do something nice for him. If the OTC time seems to go OK you might then consider out of the blue seeing if he would like to meet up for a drink after work. But again , be careful as to how he might be interpreting these things.

I guess I'm saying , take it slow. Very slow. Especially since as you describe your client I am envisioning someone not emotionionally or perhaps even mentally fit.

You sound like a nice person but it would be remiss not to mention another caution. Be sure this isn't a need YOU have ....to rescue or fix a broken man. One who btw sounds rather....uhhhh...affluent

Or turn a good client into your best/fav client.  

Is he sane?  Does he treat you really well?  No problems with haggling or anything right?

If all is well, you can (should) totally reach out to someone who you think needs a bit of humanity and kindness.  Hopefully it puts him in a better mental state, and gets you a... SUPER regular, favorite client!!! Sometimes if you just give someone extra attn and effort, it winds up really benefiting both of you

That's a very nice gesture on your part to want to do something like that for him, so just let him know exactly that and that's all.

...I have to tell you do not do this.

You have to keep the line between yourself and him clearly defined. Getting involved in his life outside of your sessions is sending him a mixed signal that will be very easily misinterpreted. Do not give him the chance to think of you as more than what you are.

I think it's an admirable trait to care about your clients. Unless you're ready to deal directly with his emotional baggage don't care too much.

I think if I was in this situation and felt compelled to do something nice for him, I'd possibly make him a nice card noting things I appreciated about him and also get him a nice gift! Something small and thoughtful.

if he's up to it.  That way you are still in a pro.vider/client relationship yet you are showing him you care about him. At least that is what I usually do with my ATFs

Judging from many posts that I have seen in here from love struck clients, it would be a bad move on your part. It sounds as if he may be emotionally unstable and if you show him this kindness, so awesome of you to do so, he will likely take it as meaning more than it is. Unfortunately not all hobbyists understand, can see and respect the indelible line that is on either side of the time we've requested of a lady.

I think you may be opening a Pandora's box if you do what you describe, but then I'm not in any way shape or form qualified, trained or experienced in giving advice on this matter. So, mine is simply an opinion and observation from my perspective.

Again, awesome of you to care about your fellow person, tread lighly.

The gift is a really nice idea, but you're right that he might read more into it than you intend. When I want to give something to a client I give them extra time. I've read here that that means a lot to guys and it's something I can give pretty easily most of the time.  

With this guy though, it sound like he needs you to listen to him talk about how he feels. Maybe he doesn't have anyone in his life who does that for him. You could do that without crossing a line, encourage him to open up, tell him how much you appreciate him coming to see you.