Jess Thoughts

Diary

Jaime and I talked until almost three in the morning. I don’t even know how the time disappeared like that—one minute it felt late, the next it was the middle of the night and neither of us noticed.

My flight out of Chicago was at 2pm. I woke up at 11:30.

For a moment I just stared at the clock, then it all hit at once—an hour drive, the airport, boarding. I panicked and called Jaime. He had already been trying to reach me. I told him I overslept, probably sounding frantic, but he stayed completely calm. He told me to breathe, that I would make it, and then walked me through exactly what to do—what to skip, what mattered, what didn’t. It was so simple the way he said it, like there was never any doubt.

So I listened, got dressed, grabbed my things, and ran out the door.

And somehow… I made it.

I walked up to the gate just as they started boarding for business class. That’s when it hit me again—two days ago he had quietly upgraded my ticket. Of course I appreciated it. But I don’t expect him to pay for my life, like that’s some requirement of whatever this is between us. For him, it’s about the little things, just like he said. He told me he doesn’t fly anything less than business, so why should I.

Then he said something that stayed with me: you receive in life what you expect, not what you hope for. Not expectation in the sense of being better than anyone else, but in believing something is right, and allowing the world to meet you there. That the world accommodates us whether we expect little or expect more.

He told me to read a book—The Magic of Thinking Big. I found it and started reading it on the plane.

At some point the man sitting next to me struck up a conversation. The usual kind. Travel, work, where I’m from. And then, like it always does, the conversation turned to whether I had a husband or a boyfriend. It’s funny how that question always comes, like it’s part of the script.

And without hesitation, I showed him the picture of Jaime and me.

I didn’t even think about it.

I just did it.

I think that was my first real step.

Now I’m sitting here, finally breathing again.

He’s coming to see me on Saturday. It feels fast, and maybe it is, but it doesn’t feel rushed. It feels natural, like things are unfolding instead of being forced. What surprises me most is how calm I feel—more at peace than I’ve been in a long time.

Now I’m stepping into something new. A relationship, or whatever this is becoming—early, undefined, still forming. And I can already feel the weight of the outside world, the judgments and assumptions waiting.

But for the first time, I didn’t hesitate when it mattered.

So maybe the real question isn’t what people will think.

It’s whether I’m ready to keep taking steps forward.