Regular Clients: The Good, The Weird, and The Obsessive

Posted by Julia | 7 min read

Let me tell you about my regulars, because they're probably the most important part of making this work sustainable long-term.

David, my widower client, sees me about once a month and has become like a weird uncle figure in my life. He always asks about school, remembers details from our previous conversations, and brings me books he thinks I'd enjoy.

Our appointments usually start with dinner where we talk about everything except why we're there. He tells me stories about his late wife, I tell him about my classes, and we debate politics and philosophy like we're old friends.

The physical part of our appointments is gentle and comfortable, more about connection than passion. Afterward, we usually watch whatever movie is on TV and he tells me stories about his teaching career.

David is the kind of regular client that makes this work feel meaningful rather than just transactional.

Then there's Marcus, my businessman who travels constantly. He's completely different - efficient, professional, focused. He books the same time slot every month when he's in town, always the same hotel, very predictable routine.

Marcus doesn't want conversation or emotional connection. He wants to relax and decompress from work stress without having to perform or manage anyone else's emotions.

Our appointments are shorter but more intense. He's not rude or cold, just direct about what he wants and appreciative when I provide it well.

Both David and Marcus are examples of regular clients working exactly like they should - consistent business relationships that benefit everyone involved.

But then there's Steve, who falls into the "weird but harmless" category.

Steve has been seeing me every other week for almost a year, and every single appointment follows the exact same script. He wants to roleplay that we're former high school classmates who run into each other at our class reunion.

I have to pretend to remember him from chemistry class (we went to different high schools), act surprised to see him, and let him "convince" me to come back to his hotel room.

It's oddly specific and kind of silly, but Steve is sweet and pays well, so I've gotten good at playing along with his reunion fantasy.

The problematic category is clients who become obsessive about the relationship.

I had one regular, Tony, who started out normal but gradually became more possessive and demanding. He wanted to book me more frequently, started asking personal questions about my other clients, and eventually suggested I stop seeing other people entirely.

When I explained that wasn't how this worked, he offered to pay me a monthly salary to be "exclusive" with him. When I declined, he got upset and accused me of leading him on.

Tony is an example of why clear boundaries with regular clients are essential. Some guys start to confuse professional relationships with personal ones, and that can get complicated quickly.

The best regular clients understand that what we have is a business relationship, even if it includes genuine affection and care. They don't try to control your other professional relationships or push for personal involvement outside appointments.

Regular clients are incredibly valuable for financial stability and emotional wellbeing. Having predictable income from people who treat you well makes all the other challenges of this work more manageable.

But managing regular client relationships is also its own skill set. You have to balance being genuinely caring and connected while maintaining professional boundaries that protect both of you from confusion about what the relationship actually is.