The Octopus
Polite discomfort
The overwhelming majority of my clients are kind, down-to-earth, and a joy to share time together.
However, maybe once a year, an unplanned discomfort arrives. The Octopus.
He messaged from a members’ advertising website designed to protect providers. His introduction email was polite. My first suggestion was, of course, to do a voice call—I enjoy hearing a human voice. To me, it reveals more than an email.
We discussed potential days to meet while I was touring near the city he lives in. Toward the end of our call, I politely requested my standard screening. He became incredibly upset. He said he was on the website to protect his identity, that he was a discreet man, and that he needed to stay that way to protect himself. He gave me a lecture about how important his privacy is to him.
đźš©Red flag number one: If a married billionaire can provide standard screening, so can a middle-aged sales rep working in a cubicle in small-town America.
I remained polite. To feel comfortable, I would simply have to do my research on the website—contacting several providers who had given him an “okay.”
🚩Red flag number two: Upon my research, I realized quickly that all of the providers he had seen were mostly in their twenties, with a few in their early thirties. It seemed odd that he would choose to contact a mature provider—particularly if the girls he had seen previously could’ve been the age of my daughter (if I had one).
About twenty emails later, the responses began to flow in. Most were one- to three-word answers: safe, nice guy, clean. No one added anything extra. He clearly looked low risk.
Still, I had absolutely no clue about his character—other than that he was safe, arrived clean, and was nice.
💋 Hint: a mature provider would probably add a bit of value—mentioning his favorite type of music, how much he loves his dog, or a detail or two that shows he has more depth than safe, clean, nice, or “okay.”
This man was a blank page.
The day of our appointment arrived, and he’d booked two hours. My hope was that he was easygoing and that it would flow.
The door opened, and yes—looking at him, he came across as nice, clean, and safe.
Less than five minutes in, though, his behavior turned bold and fast. He was very physical immediately and didn’t read or respect my comfort. He repeatedly told me—over and over—that he was “romantic,” that intimacy is important to him, and that he needs human touch to feel connected.
🚩Red flag number three: He wasn’t romantic. He was extremely needy, demanding, and disrespectful.
I gave him a bottle of water, hoping he would take a sip and breathe. We sat on the sofa in my suite. I tried to start a basic conversation to create space and give myself a moment to see if there was any real chemistry.
But in under seven minutes, I was stiff—uncomfortable—and already dreading how long the two hours would feel.
👔 A true gentleman knows when a woman is comfortable. Anything is possible. A weak man, lacking character, uses manipulative words to belittle her, force his thinking onto her, and make her insecure—so she submits without him feeling any guilt.
A date with a provider should flow and feel effortless because there’s an unspoken understanding: unlike a dating app, we both know why we’re there. There are no illusions. The subtle agreement lets us both relax—enjoy each other’s time and aim for connection.
Instead, the two hours felt like eight.
I was able to put an alarm on my phone between his nonstop neediness so I wouldn’t lose track of time. The bell rang, and I couldn’t move fast enough. I said, “Looks like it’s time for you to take a shower.”
My skin was crawling—like I was covered in ants and mosquitoes.
Meanwhile, the Octopus was still repeating that he was romantic and still wanted “a bit more.” He even commented that it wasn’t the full two hours.
I turned on the shower. I held the towel and pointed toward the bathroom. He was still being inappropriate, and my brain was now fully in survival mode.
He insisted I take a shower with him. I mentioned that I needed to text a business colleague to confirm our Zoom call because I needed to be online in thirty minutes. I had to pull the bathroom door shut behind him after escorting him in.
While he was in the shower, I set alarms on both of my phones and my iPad. They went off every two minutes until he walked out the door.
Getting dressed, he was still being physical and grabbing at me. He was talking about how “amazing” it was and how next time he wants to plan four hours.
While holding the door open, he was still trying to reach inside my robe. I reminded him—politely—that the agreement is to leave discreetly.
I must’ve been in the shower for over thirty minutes. I used soap, body scrub, then soap again—trying to wash off the disgust. My skin was raw when I got out. I turned my phone off for the rest of the day and went for a walk. I needed fresh air and a glass of wine—badly.
Two weeks later, he sent me a request for an “Okay” on the website. I deleted it.
For a week straight, he kept sending the request—over and over—for me to give him an Okay. I refused. I didn’t tell him. I just kept deleting it.
After two weeks of my deleting his request, the website contacted me. It’s owned by retired providers. They thanked me for not giving an Okay to someone I felt didn’t deserve it. I sighed in relief at their message.
🤦🏻‍♀️ I didn’t want a fellow mature provider to see that I’d approved him—only to find out that his behavior was unacceptable. If they knew me, it would break a code of trust.
💝 I share this because discomfort is information, not an invitation to ignore yourself. You deserve to feel safe—fully and immediately—and you don’t have to explain your boundaries to anyone who can’t respect them. I’m grateful I trusted my instincts, even when it would’ve been easier to hope for “maybe next time.”