Separate Lives, Smooth Setup: Discretion and Privacy That Hold

The city I used to live in is mid-size, but by the amount of gossip that goes on here, you would think it was a small town! Somehow, everyone knows a little something about everyone. And apparently, there’s nothing better to do than sit around and analyze rumors (and probably start one or two in the process).

And for the most part, this is all pretty innocent. It doesn’t really matter if the gossips talk about Jeanie from the bank after seeing her at a party with the realtor whose face is on billboards all over town, just two months after her divorce. Usually, it’s all in good faith and just something that we’re used to.

But sometimes, the gossip spreaders yield more power than they should. Rumors have been responsible for breakups, lost friendships, and job terminations. So, I knew that when I made my sugar baby dating profile, I would have to keep this one under wraps as best as I could. Mostly because I knew that my parents would not understand or approve, and I didn’t want to hurt them.

So, when I started chatting with Dillon, a CEO who spent half his time in my city and the rest of the year at headquarters in another state, I made it clear to him that I wanted to keep the sugar part of our relationship secret. He was completely fine with this, especially as someone who regularly made media appearances and was working in an industry that pitted people against each other. In other words, he had his own reasons to want to keep this private.

So, we sat down and strategized, and this is what we came up with:

Smart messaging

Our digital footprint was a top priority, right out of the gate. Dillon had seen his colleagues’ lives absolutely laid out to the public after something as simple as an email hack or stolen phone. So, he wanted to make sure that we were protected online by following some safety rules:

• No mention of sugaring or payments in the messages.
• Using encrypted messaging apps and expiring messages.
• Using a password-protected file for visual media.
• When possible, opt for phone calls over text messages.

Creating a shared narrative

Dillon and I knew that we wouldn’t be able to completely hide our relationship in our city. The gossipers were way too observant for that. So, instead, we decided that we would need to create a backstory that we could use when the nosy people started asking questions.

It was easy enough to write a story that would be easy to remember and believable: we met on a dating app, and although we were a little bit hesitant about the age gap at first, we decided to meet in person. From there, we didn’t actually have to fabricate any of the other details. We could be honest about where our first date was and how often we saw each other.

And if people started asking what our future looked like or (insert eye-roll here) when we would tie the knot, we would simply tell them, “Life is a little bit hectic for both of us right now, and we’re just taking it step-by-step. We’re enjoying the present.”

Rules of conduct for in-person meetups

Up to this point, we were feeling pretty good about maintaining our privacy online and knowing what to say when asked about our relationship. But when Dillon went in for a kiss as we sat down for our second date at the movie theater, I let him know that we would need to discuss PDA.

Sure, we had established that we were a traditional romantic couple on the surface. But I knew that even that wouldn’t be enough to quiet the gossip if we were too openly happy and lovey-dovey in person. I let him know that while his CEO buddies and colleagues would probably give him high-fives and pats on the back for being with a younger woman, I was likely to become a target for criticism and judgment if we were openly affectionate.

I think he felt kind of hurt by that, so we had a long talk about how it wasn’t personal, and I really did enjoy physical touch. But I also didn’t want to feel like all eyes were on us every time we were out in public. It was a boundary that would make me feel more comfortable, and of course, he respected that.

Discreet allowance

Just like too much affection in public would draw attention, I also knew that we could easily be found out if we weren’t careful about my allowance. An envelope discreetly slid across the table at dinner? Someone was bound to see that. Deposits into my bank account? The tellers would certainly have questions. There were, of course, privacy risks associated with cash transfer apps.

So, we decided that the best way was for Dillon to give me cash at my home (after we had established enough trust for me to invite him into my home, of course). I could then take the allowance to an ATM to deposit into my account without anyone being nosy about it.

And then, when it came to other financial gifts and things like that, we weren’t too worried. Everyone already knew that Dillon made more than I, so it didn’t surprise them that he would pay for our dinners. And when he gave me really extravagant gifts, like a designer bag or a surprise trip to Hawaii, I just made sure not to flaunt them. I didn’t post a single beach picture on social media, even though the sunsets were absolutely gorgeous!

Mutual trust

One idea that got tossed around early in my relationship with Dillon was about whether we should have a non-disclosure agreement. And I know that can be a good option for a lot of couples as long as there’s no shady behavior going on. I was even open to signing one with Dillon.

But ultimately, he brought up the fact that to draft up an NDA with his lawyer, it would mean that the sugar element of our relationship was in writing in an official legal document. And, if our relationship got out, it’s not like he could make things right by bringing me to court. He trusted me, he said, and knew that if there was a leak, I wasn’t likely to be responsible anyway.

I appreciated that Dillon saw me as someone trustworthy enough to keep our relationship private. He knew that I wouldn’t sell the story to some reporter; after all, I would also face consequences if people in our city found out the truth.

My exit strategy

One thing I learned after a few months of seeing Dillon is that even with a solid plan, keeping a secret is hard work. It’s not something that I wanted to do forever, even though I really valued my relationship with Dillon. And, I let him know that at a certain point, I planned to move to another city where I wouldn’t be worried all the time about people finding out I was a sugar baby.

Dillon was equally invested in my moving somewhere else. In fact, he suggested that I come with him on his next trip to visit headquarters so that I could get a feel for the place and, if I liked it, start looking for apartments. Luckily, I didn’t just like it, I adored it, and started meeting with realtors during the next visit. Dillon surprised me by helping me with the down payment, although I insisted on using my own savings after that.

Years later, Dillon and I continue to see each other whenever he’s in town. But now that I’m not living with the fear of being judged for being a sugar baby, we’re a lot more open about seeing other people. And in all honesty, I love that every time he comes to see me, he has gossip to share from my home city. I’m just glad that I’m not worried about being the subject anymore!