1. Is the client having fun? If the client is often grumpy or brooding, or their “fun” is anticipating things that will never happen with you, big trouble. If someone is willing to make a drama shithole of their own life, you should assume they would not think twice about trying to do the same with your life.

2. Does the client’s behavior cause you to have intrusive, unpleasant thoughts even when you are not with them. This indicates a danger of bigger problems down the road. But even if the danger never comes to pass, most people already have some negative, intrusive memories and the last thing they need is more of them. Unless you need the money for the medical treatment of someone you love dearly or something like that, this client is not worth it.

Did you actually read the letter writer’s letter? Where did she ask if it was “okay” to do anything? She made it clear that she was honest with him upfront about pretty much everything—far more honest, in fact, that I would be or suspect many others would. Your response is disproportionate to anything she said.

Are you so broke, in debt or desperate for money that you would take advantage of a confused, awkward and weaker person? Just because he’s all but invited you to take advantage of him doesn’t make it “okay.” If you owned a candy store and a confused patron insisted on buying vitamins from you, would you shrug and sell him a bag of candy anyway? Probably not against the law but maybe it’s more about what kind of person you want to be…?

He needs something you don’t have to give. Send him on his way and find someone who needs what you offer. You don’t have to like or respect him but you should like and respect yourself enough to treat a weak (and yes, slightly stupid) person with a little compassion instead of asking us if it’s “okay” to take advantage of his neediness.

So first I would recommend stating those boundaries, whatever feels comfortable to you, and if he doesn’t accept them then he’s clearly not suited to share time with you at all. What’s more likely is he’ll do anything you ask, so long as he understands that a consequence of crossing your lines is that he’ll straight up stop getting what he wants from you. The Facebook photo is a good one to start with. Let him know how you felt when you saw that, and how you continually feel with his overbearing emails. Chances are good that he wants you to feel as good as you make him feel, and he’ll get that all of this is not helping to achieve that.

The ultimate question is if the connection you feel when you are with him is worth the money and the hassle. Is that intellectual relationship you say he desires rewarding for you as well? Do you enjoy talking to him? Can you see yourself contentedly seeing him twice a week without dread? If the answer is decidedly no, then I’d say the money isn’t worth it. By letting go of connections that don’t end up nourishing us, we create room for those that do.