This is my journal entry from November 5, 2025, part of my daily autobiography Divorce Day — my real, unedited days, published in order.
I went to a speed dating event for the first time tonight. The main advice from the facilitators was predictable: just be yourself. I did that, and if the goal was to meet someone I felt a genuine connection with, it didn’t work very well. If the goal was to quickly eliminate people I don’t vibe with and not waste my time, then it worked perfectly.
The first woman I talked to was the most physically attractive of the night. She was drinking tequila and said she appreciated direct honesty. As soon as I gave her exactly that, I could feel her interest draining away in real time. She looked like she was in her twenties. I told her I’m forty-one. She didn’t like that. I mentioned that I’m getting divorced and that I have two kids. She didn’t like that either. Every honest detail seemed to push her a little farther away, and it was obvious.
The next woman had a similar reaction. When I talked about my real life, she told me it seemed way too soon for me to be dating since my ex-wife and I only started the divorce process a little over a month ago. The woman after that didn’t seem interested either once the conversation moved beyond surface-level pleasantries. I started noticing something else too: I wasn’t very curious about most of these women. It crossed my mind that maybe I’m not actually ready to date right now.
The last woman I spoke with said she was from Moldova, which caught my attention. I asked her about coming with her friend, but she said she didn’t know the woman I thought she arrived with. Right after our conversation ended, the two of them stood up together and went to the bar. Some of the facilitators and other participants commented afterward that the attractive woman from earlier was giving off serious bitch vibes, but maybe she was simply being honest—none of the men there really turned her on.
I briefly considered asking for the number of the second-to-last woman I talked with. She was a software engineer who had recently moved to Tampa and had sons who were twenty-five and twenty-one years old. She could almost be my mom, technically, but she was still attractive and clearly active. In the end, she spent a long stretch talking with another guy, and I decided it was better to just go home. The attractive woman and her friend were sitting at the bar, but I didn’t feel like approaching them. I’ve been listening to a dating book that talks a lot about approaching women and trying to pick them up, but what it doesn’t really address is this question: what if I don’t actually like the woman? Should I still approach her then?
I’m noticing that I’m having a hard time genuinely liking women right now. After being married for so long and watching that marriage fall apart, part of me seems to assume that nothing with another woman is going to go well either. When I got home, I sent a text to the woman who was supposed to come over tomorrow night. The truth is, I realized I didn’t want to see her again. I have a hard time being around the constant pot use, and the relentless negativity about the world wears me down. Politics are terrible. Everything is broken. This problem, that problem. Some of it has validity, sure, but the steady stream of it just drains me.
She tells me nobody ever listens to her, and I can see how draining the negativity is. I realized I’d only been putting up with it out of loneliness, and I don’t want to keep doing that to myself.
I keep thinking about a woman from a week and a half ago who sent me a kind, clear rejection text first thing in the morning. Now I’m on the other side of that situation. This woman genuinely seems to like me, and I just don’t feel a connection. I realized that physical attraction alone isn’t enough reason to keep seeing someone. Sitting with that realization makes everything feel bleak. What’s the point of all this? I honestly don’t know.
On top of that, I’m frustrated with my books. I talked to the dog walker today, and he said my diaries feel repetitive. He’s not wrong. Most of us live repetitive lives. At the same time, I know I go on thirty-minute tangents in these autobiographies, and maybe that’s part of the problem. Maybe I can tighten these up and focus more on what was actually different or unique about each day. Do I really need to describe going to yoga when it’s basically the same experience most mornings? Do I need to rehash the details of every AA meeting? Probably not. The genuinely interesting part of today was the speed dating. That’s what stood out. So I’m going to experiment with shortening these entries and centering them around what actually changed or mattered that day, instead of documenting everything by default. Maybe someday that will turn into something better.
I also spent time today talking with ChatGPT about what to do with my business. One idea that came out of that conversation was starting an in-person event. I’d previously thought about hosting some kind of generic breakthrough session, but it felt bland and easy to ignore. What came up instead was the idea of a money and sex mastermind. Those are charged, relevant topics that people desperately need help with—myself included. And honestly, what better way to help others than to start by helping myself? There are so many people I already know who I’d love to work with in a mastermind setting like that. It feels like a better way to actually get to know people.
Right now, I’m struggling even with the idea of dating. I don’t really want to pick women up or go on dates because I don’t know these people. Take the woman from yoga, for example. I’d like to know her better, but do I actually want to go on a date with her, with all the pressure that comes with it? As soon as I start dating a woman, my focus narrows to sex. That becomes the goal—find out if the sex is good, then decide what happens next. It makes the whole process of “getting to know someone” feel tedious and transactional. I’d much rather have someone like the woman from yoga come to a mastermind, along with other people I already know, and have us work together. Maybe chemistry develops naturally there. Maybe people find ways to collaborate or make money together.
I even thought about pricing it at $69, and then immediately felt hopeless about that too. The voice in my head says nobody will come, that I’ll announce it and end up alone again. Today just feels heavy and pointless in that way. At least my mom told me the letter I wrote to my brother is nice. That matters. I’ll send it soon and wrap that up. For now, that’s enough.
If you connect with how I live and think, you can follow the rest of my days on YouTube in my Life playlist.