I have a client that normally after our session is over we generally part soon after. However, this last time he actually wanted to talk. I had no problem with that whatsoever.  
 
He started out the conversation by saying that people suck. He then says that I am always happy and I am always smiling but it was if he couldn't understand why. He said it like it was a bad thing. I paused for a second and I said yes, some people do suck. But I'm generally a happy person because I'm healthy, I'm alive, and I'm making more money than I ever have in my life. Things could be much worse.  
 
So he gets quiet for a second and says I take care of my entire family. Everyone. My parents. My siblings. Everyone. They always call for money. My siblings are over 30 with degrees. So I said to him, do you feel taking advantage of or that you aren't appreciated? Do you feel like they are your responsibility? He said it made him feel good because they have no one else, but it does take a toll on him. He said he has so much extra income that it's ridiculous so it isn't like he can't help them. And then he got completely silent. I felt bad.  
 
For a few days now, I've been thinking about reaching out to him and asking if he'd be willing to meet with me for a "cool surprise". I'm sure he would, but here's the thing. I honestly just want to take this guy out for a nice dinner, chop it up, have some laughs, and then go our separate ways. It would be a way of showing him that not ALL people suck and that someone can do something for him without wanting something in return. This would be me saying hey I appreciate you and I appreciate your consistent business. I know you work 80+ hours a week and I just wanted to do something nice for you. That's it. That's all.  
 
Do you think this gesture will be taken the wrong way? Am I doing too much? Do I take this chance of trying to cheer someone up only to risk that he may think it's more than what it actually is? Or just don't do it LOL

scribble a note...

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".  

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?

While there are many of the "never ever cross boundaries" opinion, plenty of us here know how to have casual fun without looking for anything deeper. Go with your gut, but if you're unsure then don't do it.  

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.

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.

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.    

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.

+1 eom.

Starts out by saying people suck ... then mentions everyone in his immediate family. Huh??

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

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.

Gagambler is a 100% right! I wouldn't do it either. Some people thrive at it and honestly you are professional people pay for your time now, so to do it for free will never make that relationship the same.

Much like the underprivileged kid who makes it and signs a pro sport contract, everyone comes looking for a handout and he feels obligated since they're "family."

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

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.

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.