Jess Thoughts

I couldn’t sleep tonight. The whole day was so good — a little crazy, a little chaotic, and wildly unconventional in the best way. The training itself has been incredible. The people, the discussions, the way everyone challenges each other — it’s exactly the kind of environment I hoped it would be. It’s my personal life that suddenly seems to be taking a strange detour. I can feel it happening. The best way I can describe it is like being on a roller coaster. You climb slowly up the first hill and you know exactly what’s coming next. You’ve seen the track, you understand what’s about to happen, but once you’re strapped into the seat you have absolutely no control over the ride. That’s where I feel like I am right now, climbing the hill. Two very different paths seem to be opening in front of me, and sooner or later I’m going to have to choose one — or pull the emergency stop and get off the ride completely.

Tonight Anna and I went to dinner with Steve, Isaac, and Daniel. He chose a Michelin restaurant in Chicago. I’m not bragging, but I had been there before with my parents once, so I knew what we were walking into. Still, it was a very nice gesture and a thoughtful choice for the group. Daniel paid for everything. The evening was genuinely pleasant — good food, easy conversation, the kind of night most people would probably call perfect. At one point during dinner Daniel tried to hold my hand under the table. Well… he didn’t actually grab it. It was more like he “accidentally” touched my hand and left it there just long enough to see what I would do. Then he looked up at me, almost studying my reaction. It was actually kind of cute. I smiled at him and slowly moved my hand away.

I don’t know. He’s a great guy. Really. Handsome, confident, successful, generous. From everything I can see there are no red flags at all. If anything, he might actually be too perfect, which is a ridiculous thing to say. But there is something about him I can’t quite put my finger on. Not something bad — just something that doesn’t quite connect for me. And honestly… I’m not here to find a man. At least that’s what I keep telling myself. Because at the exact moment Daniel was testing the waters with that little hand touch, I found myself pulling out my phone and texting Jaime.

My heart jumped the second I hit send. That probably says enough.

He answered immediately. I asked him what we were going to do next, and he started teasing me right away, calling it a “date” and accusing me of being the one who was asking him out this time. I actually blushed sitting there at the table and looked around quickly hoping no one had noticed. We ended up flirting back and forth about friend zones and who was putting who into one. He’s the wrong man for me — completely wrong — and yet somehow he feels exactly right at the same time. He has this way of keeping me engaged while never quite revealing what he’s thinking. He lets the conversation breathe. He lets me wonder. The strange part is I never feel pressure with him. I feel seen. At the same time there’s tension between us, real tension, the kind that makes you aware of every word you say.

After dinner the group wanted to go dancing. Daniel stood up and started leading me toward the door while everyone gathered their coats. My mind was spinning. Suddenly I realized I needed to end this before it went any further. It wouldn’t be fair to him. I don’t lead people on. So I excused myself to the ladies’ room. Anna followed me immediately and asked if I was okay. I told her I wasn’t feeling well. She looked at me for about two seconds and started laughing, telling me I was crazy and that I needed to give Daniel a chance because I wasn’t going to find better — handsome, generous… and handsome again. She said he was completely into me. I laughed and told her I really was sick. That time of the month. She paused for half a second, smiled, and nodded like she understood everything. She had just given me my escape. I told her she should go with them and have fun, and she agreed.

When we walked back out she gave Daniel a little wink and quietly explained the situation. He understood right away. He gave me another hug before they left — but this time he kissed my cheek. I made sure to hug everyone else too so it didn’t look strange.

But my heart was racing.

The moment they left I pulled out my phone and texted Jaime again. We made plans to meet in the morning. And now I’m lying here wide awake, realizing that the roller coaster might be reaching the very top of that first hill… and I have no idea what the drop is going to look like.