Jess Thoughts

“Another day, another dollar,” is what my dad would say, and I found myself thinking that as I walked back into work this morning. It felt like stepping back into a different world after everything that’s happened over the last couple of weeks. The training already feels distant, even though it just ended. Still, I can feel how much it changed me. I’m more aware now—of how people communicate, how teams function, how subtle dynamics shape everything in a corporate environment. I’m watching more, listening more, trying to apply what I learned instead of just going through the motions. My dad’s voice is always there in the background reminding me to be deliberate, to accomplish something each day, no matter how small. It doesn’t have to be a grand achievement. Just forward motion. Just swing the bat.

Anna has become a big part of my daily rhythm here. It’s strange how quickly we’ve connected. She feels like someone I’ve known much longer than I have, and I’m realizing how much I needed that. For all the travel and experiences I’ve had, there’s a part of me that’s been disconnected from everyday life, from having people around consistently. Now I’m stepping into that, and it feels… grounding. At the same time, I know there’s something I haven’t told her yet, and it’s sitting there quietly in the background of every conversation we have. We’re going to dinner tomorrow, and I think I’m going to tell her about Jaime. I’ve been putting it off, not because I’m unsure, but because I don’t know how it will be received. I tell myself I don’t care what people think, but the truth is, I do care what she thinks.

Then there’s Jaime.

I still catch myself pausing when I think about it, like I’m trying to make sure this is actually real. I wasn’t looking for anything, and yet here I am, in something that feels more defined than I expected, but still new enough that I hesitate to label it too strongly. What I do know is how I feel when I’m with him. It’s different from anything I’ve experienced before. There’s no pressure, no performance, no need to be anything other than exactly who I am. He listens—really listens—and not in a passive way. He hears me, processes what I’m saying, and responds in a way that makes me feel understood. That’s rare.

We’ve talked about the age difference openly now. It’s not something hiding in the background anymore. I know how it looks from the outside, and I’ve already heard the comments—sugar daddy, assumptions about motives, people reducing it to something transactional. It doesn’t bother me the way they probably expect it to. They don’t know anything about what this actually is. Jaime doesn’t pay for my life, and I don’t expect him to. What he does is different. It’s thoughtful. Intentional. Like upgrading my flight without making a big deal about it, or remembering something small I mentioned in passing. It’s never about showing off. It’s about paying attention.

At the same time, I’ve had to be honest with myself about how I present things. When I visited him, I dressed more provocatively than I normally would. I’ve thought about that a lot. Part of it was curiosity, part of it was testing him, and part of it—if I’m honest—was wanting him to feel proud to be seen with me. I understand how men can be about that, the idea of having someone attractive on their arm. I don’t mind that role, but I also know that’s not all I am. The important part is that he doesn’t treat me like that’s all I am either. He sees past it, and that matters more than anything.

Work and life are starting to blend in ways I didn’t expect. I came here focused on building something, on moving forward in a structured, predictable way. Instead, everything feels like it’s evolving at once. Even outside of work, opportunities are appearing. A photographer friend reached out and asked me to model for a contract—cocktail, promotional, wedding work. I agreed. It’s something I enjoy, and I get paid for it. I made it clear I won’t do anything risqué. That’s not something I’m willing to step into. I’ve learned enough to know where my boundaries are, and I’m not interested in compromising them.

What I find interesting is how quickly people try to define you based on fragments. How you look, what you wear, who you’re with. The assumptions come fast, and they rarely reflect reality. I’ve heard the whispers, the quiet judgments, the simplified stories people create to make sense of something they don’t understand. It doesn’t change anything for me. I pay my own way. I make my own decisions. And I’m comfortable with that.

Jaime and I have also set expectations—real ones. Clear, direct conversations about boundaries, about respect, about what this is and what it isn’t. There’s something reassuring about that. It removes the guessing, the uncertainty that usually comes with something new. It doesn’t make things simple, but it makes them honest.

And maybe that’s what this all comes down to.

Work, relationships, everything—I’m starting to understand that it’s not about finding something perfect or predictable. It’s about finding something real and choosing to move forward in it, deliberately.

I don’t know exactly where this path leads yet.

But for the first time in a while, I feel like I’m walking it on my own terms.