Dear Tits and Sass,
Last February, I met Phil off a sugar dating site. He was extremely effusive in quasi-personal affection towards me during our first meeting, to the point that I realized he was an attachment risk and considered not seeing him again. (He’d had a recent and extremely nasty divorce.) But I agreed to a monthly arrangement of x dollars/month for indefinite weekly meetings and saw him three times total. In addition to sex, he wanted an intellectual relationship.
Between our meetings, Phil frequently wrote me vaguely romantic emails, with very familiar addresses and conclusions (things like “dear love,” etc.). I am married and he knew that. Eventually he was sending me such intense emails that I concluded he actually thought he had fallen for me. The last piece of evidence for me that things had gone too far was when I went over to his house and found a picture of myself on his mantel: He had learned my real name from a careless mistake I made, found my Facebook, and got the picture from there.
I didn’t return his calls or emails for awhile. He sent me several distraught emails and I finally emailed him, apologized for being uncommunicative, and told him that I couldn’t see him anymore because I was concerned he was getting too attached. I was pretty blunt, but toed the line between being a person breaking up with a lover (as was appropriate to the stupid sugar game we were playing) and an escort cutting off a client (I, for example, referred to myself explicitly as an escort/sex worker in the email). I told him my role in his life should be therapeutic and motivational, not romantic, and that I did not think that was possible, basically.
He sent me a recent email proposing we keep seeing each other, just less frequently, and I did tell him I’d respond to it (oops—maybe shoulda held my cards), and I am hoping there is something I can do to let him go. I also am nervous because I (a) don’t want to acquire a stalker or something, and (b) he has my real name, which means that he could conceivable out me if he felt sufficiently jilted. Don’t know if he’d do that or not. (My husband knows about all of this.) What should I do?
Sincerely,
Unhappily Loved One
Beatrice Darling (Harlot): You have a client who is in love with you, and that means that he has no other substitute for you. That kind of infatuation can lead to a goldmine if you are willing to finesse him a little bit, and are able to keep your boundaries intact.
He knows your real name, which sucks, and he is behaving like a world-class supercreep. Chances are, though, that he’s just lonely and smitten with you, and would never actually hurt you in real life, or try to out you. Nothing you’ve said about him indicates that he’s unstable, just deeply lonely. If you want to continue seeing this guy—and there’s potentially a very good financial reason to do just that—then you need to be honest about what is pushing you away, and give him very, very clear boundaries to respect so that he knows exactly how you expect him to behave. Tell him that it’s not okay to cyberstalk you. He will still do it, but he will know exactly what his place is in your life, and that it’s not cool of him to try and inject himself into your life. Make your Facebook private to limit his access. Try using words like “hurt” or “shocked” that he would “invade your privacy” rather than “you are a creepy stalker man and if you were not loaded I would just file a restraining order and be done with it.”
Also, you need to make the details of your financial arrangement clearer. Right now, you’re in a good position to negotiate. He adores you. He’s willing to shell out some cash to keep you around. If you agree to keep seeing him, agree to once a week. Or 1-2 times a week. More than that, and you’re going to feel suffocated. Less than that, and he might as well just book regular sessions with you. It will help you stay sane to check off your visits and know that he won’t be expecting you to come back until next week.
Never give more than you’re comfortable giving, and don’t let his feelings for you cloud your financial agenda. Don’t give him more than you ordinarily would just to create a sense of reciprocity, but don’t run away from those paydays, either, if you can help it.
Charlotte (Escort, Failed Sugarbaby): You’re right; you don’t owe him anything. I’m a crusty old hooker so I might be less tender-hearted than most, but there’s only so much sympathy I can extend to a man who has decided he’s in love with you after you met a mere three times, and who knows you’re married. I’m not encouraged by his attempt to see you again after you broke it off. He sounds desperate and emotionally vulnerable to the point of having no self-preservation instincts left.
There’s no good way for you to see him again, given what you’ve indicated about how you prefer to work and what makes you comfortable. But if you need the money, I suggest agreeing to dates with him only as a regular client and keeping contact outside of that minimal. In other words, make him arrange a set period of time to see you in advance and pay for that time by the hour so the boundaries are clearer. Then limit his dates to as few as possible, with minimal contact in between. If you’re going to cut him off entirely, don’t let your kind nature lead him to believe there are any openings for contact. State unequivocally that it’s over.
Annora Quinn (Escort): I think the only thing you can do in this situation is to completely cut him off. If you let him hold you hostage with his knowledge of your personal life, there will be no end to it. Every time you try to break it off he will bring it up, and there is the risk that he will use it to extort more meetings or push your boundaries sexually. If he is going to try to use your identity against you then waiting for a later date won’t make it easier to deal with; if he tries to out you on social media or by other means you can deny everything, say you acquired a stalker from Facebook and reminisce about a time when we didn’t live so much of our lives online.
The benefit of being involved in such a stigmatized industry is that Phil won’t be able to out you without outing himself, something he probably doesn’t want to do because it would not only mean admitting that he is a client, but also that even women he pays to be in a relationship with don’t want to see him, which is a big blow to his ego. Additionally, most civilians see sex workers as being so “other” that your friends and family probably can’t imagine anyone they know being one. They won’t want to believe him.
I’ve had to “break up” with both real clients and sugar daddies because of neediness and the men from the sugar dating sites are always so much worse. They get so emotionally invested. I would suggest a polite but short email explaining that you will not be able to see or communicate with him anymore and no more contact after that.
Sabrina Morgan (Companion, Domme): Given that he is displaying stalker risk behavior (rapid attachment/effusiveness, obsessiveness, inability to distinguish fantasy from reality, lack of boundaries/respect for privacy) I would recommend just not responding. None of this is your fault, but to that mindset attention is encouraging. For simple bad boundaries, an explanation would probably be fine, but if you’re concerned for your safety it’s best not to respond. If you respond and mention any obstacle that’s keeping you two apart he’ll treat it as an objection to be dealt with, not a reason to withdraw.
Should he persist in contacting you, save everything. If he makes any threatening communications or actions, instruct him not to contact you further and tell him you will pass on any further contact to the police. In this type of situation, how you met him (sugar daddy website) is less important than what he’s doing (harassment) to the authorities involved.
If you are a current sex worker facing a work-related challenge, you can email info [at] titsandsass.com and we’ll do our best to help or call in a guest who can. (Please no “how do I get started hooking” questions. This is for those who are already in the biz.)
I’ll have to agree largely with Beatrice in that his behavior probably more typifies that of a lonely, recently divorced man than a stalker. And lonely men, especially those from sugar daddy dating sites, are an awful lot like young children: they want to push and push and push just to see how far they’ll get. My experience with the sugar world is probably a common one among pro sex workers, that at the end of the day escorting is just more desirable because clear boundaries are necessary and therefore expected.
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.
This man is clearly confused and immature but at least he’s been honest (with himself and you) about needing an emotional connection. Clearly that is not what you offer or want to engage in. How is this not a black and white issue for you?
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.
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.
I would suggest two points to ponder in general with clients:
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.
“But I agreed to a monthly arrangement of x dollars/month for indefinite weekly meetings and saw him three times total. In addition to sex, he wanted an intellectual relationship.”
I don’t see you setting up your boundaries properly early on your relationship; after relationship progressing, you cold turkey this guy, it could drive some people seems overly obsessive, man tends to logic over emotional reasoning skill. It not too late to setup boundaries if this guy can take hints, If he wouldn’t, run away fast.