This is my journal entry from November 1, 2025, part of my daily autobiography Book 5 — Daily Autobiography — my real, unedited days, published in order.
Last night was a big one for me — I had sex for the first time since my separation. It felt good, and it shifted something in me.
Let me back up a second. This morning I started out feeling alone, like I really wanted some connection. So I went through my phone and decided to approach it logically — almost like sales. I’d use the contacts I already had, send out some warm messages, and see who might want to get together. I found eleven women I thought one of them might be interested.
What’s even better is I asked ChatGPT for a workflow. I didn’t want to send something blunt and crude right out of the gate. Some of these women are friends, some I hadn’t talked to in a while, so I just wanted to send a little feeler and escalate from there if there was interest.
I also messaged my friend from yesterday to see if he wanted to be my wingman. He messages back saying, “I don’t think that’s good for you, bro. I think you should just stay in.” And I’m like, nah. I’ll tell you what I’m going to do — I’m going to get out there and connect with someone. That’s what’ll help me. Not sitting around picking at what’s broken inside, but actually being with another person.
So I messaged eleven women first thing in the morning. Generic messages. I’ll tell you about the one that actually led somewhere. This is a woman from massage school. For privacy, I’m not putting her name out, which honestly makes it easier to talk more directly.
I scroll down. First thing in the morning. I hadn’t texted this girl in about a month, because I dropped out of massage school a month ago. The last text with her was October 11th, so like three weeks ago. She had sent me one, two, three, four, five, six, seven messages that I had responded to. Then she sent me seven more messages and I didn’t respond.
So I send her a message this morning. I literally wrote this with ChatGPT. It says: “Hey [name], I was thinking about you and realized I dropped the ball on our messages. Sorry about that — life got a little hectic for a bit with the divorce and moving out. How have you been?”
She messages back, talking about school a little bit. I literally copy-paste that into ChatGPT and I’m like, tell me something to say back. I don’t want to use my brain power on texting. Texting is annoying to me. There are things I use my brain power on — like this — but texting? Just write it for me.
I screenshot what she says, drop it into ChatGPT, and I say, “Write me a text that escalates things and talks about what I’m doing.” So I send a message back saying, “Sounds like a tough stretch, but I’m glad…” dot dot dot. And at the bottom it says, “Would love to meet up with you here in St. Pete and show you around sometime.”
She texts back, “That sounds great. When would you like to do that?” I text back, “I’m available tonight. How about you?” She says, “What do you mean by night?” I say, “I should be available as early as 5 p.m.” And she says, “Well, what do you want me to be up for? And are you aware it’s Day of the Dead?” And I’m like, I don’t even know what Day of the Dead is.
But then talking to her later, she reminded me the movie Coco was about that. And I did see that. So I messaged back, I don’t know what the fuck Day of the Dead is, but we can meet up at the pier or the Dalí Museum. She responds that she doesn’t want to do anything that requires spending money if she can avoid it. And I’m like, shit, that’s what I’m talking about.
So I paste it into ChatGPT again and I’m like, I don’t know what to do with this, but try to get her to come spend some time at my place. ChatGPT gives me this response: I’m down for that. Honestly, I just want to spend time with you. The rest doesn’t matter. Apparently that was the right wording, because she responds, Can we meet somewhere really gentle on my nervous system, like your house, and then wander together from there? And I’m like, yes. Yes, we can do that. I would love to do that — and it costs zero dollars.
So I send her my address, and she ends up arriving about thirty minutes late, which was totally fine because I took the kids to the store. I took them to Goodwill. I’m up in that thrift shop shit. Ninety-nine cents. I’m looking for some used polos, grab a couple off the shelf. The kids have fun going to the thrift shop with me, and it gives my ex-wife a little bit of time to herself. That all works out perfectly.
Before all that, though, let me back up, because I don’t want to skip the 10:30 a.m. Power Flow. That class got interesting. I go to my yoga studio and it feels like everybody is there. Two people I know from AA are there — one is in front of me with her girlfriend, the other guy is to my left. Our local representative is behind me. I’ve got an open spot to my right. The girl I tried to pick up last week is up front with her friend, and I can feel the awkwardness. I’m like, fuck, I’m going to have to deal with this at some point.
Then the woman from yoga comes in and puts her mat down to my right. And I’m like, oh shit. So I start talking to her. And of course, my shitty attitude completely disappears because now I’m feeling good and a little turned on. Oh, and let me say this too — I’m not leaning on the solo stuff anymore. At least not today. Yeah, let me interject right here. Bitch, you say that now, but next time you’re in the mood you probably will. Well, we’ll see. I’m done with the routine of forcing something that isn’t there.
So the woman from yoga puts her mat down next to me and we have a great conversation. I’m asking her all kinds of questions, and by the end of it I’m feeling pretty good. Her romantic situation is a little complicated, but I’m like, that’s fine — I’m getting divorced, mine isn’t exactly simple either. I get her number. I follow her out to her car — definitely romantic, not creepy, although I’m sure some people would disagree.
She’s got to go pick her kid up, so I hustle. I grab my phone and walk out to her car with no shirt on because I don’t even have time to put it on. She’s already moving. I get her number right there in the parking lot. And I’m like, alright — next time we’re generating leads, we’re adding her to the workflow.
Then after class, I’m ready to go help my sponsee move some stuff. First I go home and have breakfast with the kids, then later my ex-wife and I have lunch together. She bought Ethiopian food. And while we’re eating, we talk about dating.
I tell her straight up — look, I’m going to start seeing people, and out of respect I wanted to give you the first option before anyone else. I know we’re getting divorced, but I figured I’d offer. She’s like, no, I’m good — I think that would make our situation complicated. And I’m like, you’re right, it would. So I’ll look elsewhere. That’s okay. We talk it through calmly. No drama. I eat this big plate of Ethiopian food that my ex-wife and the kids picked up at the Saturday market earlier that morning. Finish the whole thing at her house.
Then I head out to go help my sponsee move on a full stomach. I drive about twenty minutes to his place, and you know how people are when they ask you to help move. They always minimize it. Oh, it’s just a pillow. Just grab this pillow and put it on the bed. Super easy. I’d do it myself, but I just want to see you and hang out. I get there and there’s a dresser, a bed, fucking barn doors, all kinds of shit. I’m like, man, from now on I’m asking for pictures. If I’d seen this dude’s garage ahead of time, I’d have told him, fuck that, hire a moving company. But I’m there already. Gotcha, bitch. He got me.
So we start moving stuff, and he shows me this bedroom in the house. Him and his wife are about to have their third kid. He’s like, yeah, we might rent this room out. I’m like, shit, how much? They say maybe thirteen-fifty. I’m like, damn, that actually looks pretty nice. I keep it in mind for a second. Then reality kicks in. It’s twenty minutes from my ex-wife’s place, there are three kids in the house, it’s loud as hell, and I can’t be recording audiobooks with kids running around screaming. I love having my own place. I need my own space where I can record whenever the fuck I want—6:23 p.m., 11:30 p.m., whenever. I want to be able to sit down and record a book without interference. So yeah, renting a room there isn’t happening.
Then, of course, while we’re moving one of these big-ass barn doors—the kind that hang on a track like a giant closet door—it nails me right in the ankle. We’re sliding it over and my ankle is right there. Whap. Straight into it. Thank Myself I move quick. Yoga, balance, reflexes. As soon as it starts hitting my ankle, I shift the weight off it. Otherwise, that could’ve been bad. I’m like, goddamn it, that’s what happens when I take my amateur moving ass and try to help people. We finish moving everything—dressers, bed, barn doors. Honestly, it wasn’t that much stuff, but it still took about an hour. I did a small fraction compared to what he’d been doing all day, and that was enough for me.
After that, I went straight home, getting ready for the night. But first, kid logistics. I drive back to my ex-wife’s house, grab the kids, and we go to Goodwill. My son is only wearing underwear and talking about how he just wants to stay home when I arrive. My daughter wants to go to Goodwill. My ex-wife is clearly trying to get a little time to herself. I’m like, look, I’ll give you five minutes. Let’s just get in the car and go. And somehow that works.
They’re both ready, and we actually have a great time. My daughter is looking at everything—clothes, decorations, random stuff. My son is into the tables and furniture and toys and Halloween decorations. We spend twenty-eight dollars total. I grab two polos—cheap, secondhand, kind of nasty-looking polos. One of them is a small, and I’m like, shit, I don’t know if that’s a good thing or a bad thing that I can still fit into a small polo, but I think I look good in them. They feel fine. Six dollars each. Why not. I also buy the kids some stuff to paint their hair and color their faces, which they immediately start doing in the car as soon as we leave. We move pretty fast through Goodwill, even though it’s the big one up by the Gandy Bridge.
Since we wrapped up early, instead of dropping them straight back at my ex-wife’s, I take them to my place for a bit. We play checkers. My daughter beats my son. Then I beat my daughter. So far, neither of them has ever beaten me in checkers. I mess up once or twice with some dumb moves, but I still manage to win. I get a bunch of double jumps on my daughter. At one point, I even let her double-jump my king and another piece, and I’m like, Jesus. But we have fun. It’s a good moment.
Then I drop them off at my ex-wife’s a little before five and head home to shower. I’m like, all right, let’s get ready. Tonight’s happening. And here’s what’s funny. It’s amazing how differently people look to you depending on where your head is at. Back when my ex-wife and I were together, this woman from massage school—she’s got this very unique haircut, shaved on one side, longer on the other, dyed bright colors, lip ring, nose ring, the whole thing—I remember thinking she looked kind of out-there, but interesting. That’s literally what pops into my head.
She always looked like the most interesting person in massage school. She was born a year after me. And back then I remember thinking, yeah, she’s all right. So today I’m thinking, I hope tonight goes well. And honestly, at this point, I’m committed to seeing where it goes. I’m committed.
So she arrives. She pulls up in her Tesla, which I remember from school. She lives with her parents in Sarasota, so I’m thinking, you’ve got this new car, you live with your parents, and you’re willing to drive an hour up here—clearly you’re looking for something tonight too.
She pulls up right around 5:30, almost on the dot, texts me a picture of my house like, “Is this the right place?” I’m like, yeah, yeah. So she gets out and comes in, and immediately I’m like, damn—she looks even better than I remember. Maybe she really does, or maybe I’m just so starved for connection right now that everyone looks better. It’s probably both. I haven’t been with anyone in about a month, and that’s the honest truth of where my head’s at.
She comes in with hula hoops and good energy. She’s fun. So we start talking, and she asks if I want to go anywhere. I’m like, nah, I want to spend more time right here. Neither of us wants to spend money. When she parks, she even asks if she needs to move her car in case we’re going somewhere. I’m like, no, we’re staying here.
After about thirty minutes of talking inside, she wants to go for a walk. And immediately I’m like, this is not a great idea. My mom lives in this neighborhood. My ex-wife lives in this neighborhood. My ex-wife’s parents live here. Her sister lives here. I don’t want my ex-wife driving by while I’m walking around with some other girl. It’s too soon for that. I don’t want my mom or my ex-wife’s family or half the people I know in this neighborhood seeing me and being like, who’s that?
At the same time, I’m not embarrassed to be out with her. She’s cute, she’s attractive. Would I be showing her off all over town right now? No. But she’s cute enough that I can walk around the neighborhood with her and not feel like I need to hide. So yeah, we go for a walk. She finds a ball in the street and we start kicking it around for a few blocks. She’s got her hula hoops. We’re laughing. And I’m remembering all these dating books—escalate, escalate—so I start holding her hand on and off while we walk. And I’m thinking, I’m pretty sure she’s into this.
My friend said the other night at the Vinoy that people often decide pretty fast whether they’re interested in you. I figured she’d made up her mind early. Why else drive an hour up from Sarasota? That’s not something you do just to take a walk. And let’s just say it out loud: women have desire too, just like men—they’re often more conditioned not to say it openly. If you can meet that honestly, in a way that’s completely consensual and enjoyable for both people, that’s where real connection happens.
We went for a walk around the neighborhood, and internally I was already a little impatient. I’d worked out earlier and didn’t need the extra steps, and part of me just wanted to get back. We circled the block, then somehow stretched it into a mile and a half. When we finally got back to my place, I moved in a little, testing whether she wanted to get closer, and she pulled back with a “whoa, slow down.” In that moment I realized this wasn’t going to be quick or easy—I was going to have to slow down and let it unfold. I made a conscious decision to treat the night like a marathon instead of a sprint. She smokes weed every day and smelled like it, which is a turnoff for me, but I let it go for the moment, while also filing away that whether I’d want to do this again was a separate question.
She had arrived at 5:30, we finished the walk around 6:30, and then we talked until 1:30 in the morning. Seven hours. Seven hours of talking, and easily eighty percent of it was her. I had to actively quiet my own mind, almost coaching myself internally to shut up and listen. The strategy was simple: don’t interrupt, don’t debate, just let her feel heard. If listening was the price of admission, then I was listening. She even said it outright—that nobody had listened to her like this in a long time—and I just kept nodding and holding space while she unloaded about her life and the state of the world. It felt like she needed to get it all out to feel safe. As the hours passed, we got more comfortable and physically closer, both of us coming from massage school and instinctively shifting around, until eventually she said she wanted to go to bed. It felt surreal, like we’d talked an entire lifetime into that couch, hour by hour.
She did tell me some genuinely entertaining stories about massage school, and there were moments where she had me laughing so hard I was almost doubled over. She says funny shit naturally, without trying, and that helped a lot. We cried together too, which surprised me in a good way. She shared some very raw emotions, and I’m glad I had listened to that audiobook Dating Sucks beforehand, because it emphasized something I was watching happen in real time: women often communicate emotionally rather than logically. Men tend to narrate their day like a checklist—this happened, then that happened—while women are transmitting how they feel, not just what occurred. Even listening back to my own audio, I can hear emotion in my voice, but the words themselves are often just facts and jokes strung together. Hers were different. Hers were feelings, layered and flowing. Anyway, thanks for that little sidetrack, Jerry. Don’t worry—we’re picking the story back up in a minute.
After all the shifting around, we ended up spending a few hours just on the couch, both of us restless and moving. Around 9:00 p.m. she announced she was hungry, and internally I was like, there is no way I’m taking you out to eat right now. I generally don’t eat after 9:00, and honestly that wasn’t the direction I wanted the night to go either. I told her I had snacks—fruit, a LaraBar—and joked that I hoped she wasn’t allergic to peanuts. And yes, Jerry, that sounds a little mean. No, I don’t hate women—I love and respect them, which is part of why I connect with them. Honestly, this would probably be more suspenseful if I hadn’t already spoiled that we ended up together, because in the moment the uncertainty was very real.
I was about ninety percent confident this was eventually going somewhere, but that other ten percent was loud. Part of me thought, if she talks all night, unloads everything, and then leaves, I’m going to sit here afterward feeling pretty low. I just wanted her to say everything she needed to, quiet her mind, and let things unfold naturally. At 11:00 p.m. she finally said, “Let’s get into bed,” and that felt like the confirmation I’d been waiting for. Even then, it was a couple more hours of talking. She’s genuinely interesting—she’s lived all over the world and had all kinds of experiences. There was also a lot of venting about the state of the world. And yes, I hear the irony, since here I am narrating my own experience. The difference, in my mind, is I’m just trying to acknowledge the absurdity of what I’m living through and find some humor in it.
By around 1:00 a.m. we were both yawning and I was straight up tired. Around then, she finally kissed me. I started to realize that in her mind, kissing meant more, so she’d been holding off as long as possible. I’d gently tried a few times earlier and even talked it through with her, because she’d shared that she wanted very clear boundaries and didn’t want anything done to her body without being asked. There’s a balance there—you don’t want to turn intimacy into a permission-slip exercise and kill the vibe either. There were several moments where I thought she was about to kiss me and didn’t, until finally she did.
She had told me about her trauma history, so I knew this was going to move slowly. I kept offering reassurance, telling her how glad I was to be there with her. At one point I told her I’d been feeling really lonely lately and that being there with her felt like the opposite of loneliness. And yeah, I can hear myself now—that was probably the moment, wasn’t it? But it wasn’t a line. It was true. I got genuinely romantic, and things grew from there.
Things moved slowly from there. What was interesting was that, as far as I could tell, the whole night was sober. She didn’t smoke while she was with me, even though she smelled like weed when she arrived, and I don’t think she was on anything else. Given her history, that actually felt meaningful.
What stood out was how into it she was, how present and enjoying herself—and I remember thinking, this right here is one of the reasons I’m genuinely glad I’m getting divorced. Toward the end of my marriage, that kind of ease and enthusiasm just wasn’t there anymore.
At the same time, my mind was a mess. And then my body just wasn’t cooperating—I couldn’t perform. I remember thinking, I am not going to live the rest of my life like this. But instead of making it worse, she handled it beautifully. She talked about the emotional side of it, about how men’s bodies need to feel safe too. And I cried. I fully cried—lying there with her, exhausted, vulnerable, exposed. That kind of openness from her, in that moment, meant a lot.
At some point it struck me how much the listening and the patience had mattered. All those hours of really paying attention to her, making her feel heard—that was the real foreplay. She even remarked on how present I’d been. It drove home something I keep learning: connection and attention matter more than any technique.
We talked openly about what each of us liked and where our boundaries were. She communicated everything so clearly, and honestly, that openness was one of the best parts of the night.
She told me straight up she didn’t want to be monogamous—she wanted to be polyamorous. I told her I felt the same way. I wasn’t trying to be possessed by anyone; I was fresh out of a divorce and absolutely not looking for a relationship. That alignment felt good. We also talked about protection, and for the first time in maybe ten or fifteen years, I actually thought, yeah, we should be responsible about this. She immediately agreed—it was one of her boundaries too. I appreciated how clear and grounded she was about all of it.
There was a stretch where I was lying there frustrated, trying to stay calm, and also feeling sad and missing my ex-wife. There’s a comfort and a history with someone you’ve been with for years that you just don’t have with someone new. It was an emotional night as much as anything.
But then something shifted. I slowed down, relaxed, and things eased up. It was getting close to 3:00 a.m. by the time we came together, and after all that buildup, it finally felt right.
What struck me was just how different it all felt—it had been fifteen years since I’d been with someone new, and everything about it was unfamiliar in a good way. It felt good. Really good.
It didn’t last super long, but it was good. I’ll just say my hands—the same hands that made me a pro gamer and a top-twenty Facebook partner back in the day, that used to dominate online—turned out to be good for more than video games. I cracked myself up with that one.
Afterward, what stood out more than anything was how desired I felt. It had felt like my ex-wife hadn’t really desired me in a long time, and this woman clearly wanted me there. That felt amazing—that was the part that mattered. There was even a Britney song stuck in my head about being a “womanizer” after messaging all those people that morning. The real takeaway: women have desire too. Let’s not pretend they don’t.
Then she went to the bathroom and left the door open, which my ex-wife never did in fourteen years together. I remember thinking, huh, that’s new. I mean, we’d just been intimate, so I guess it’s not unreasonable. Then I did the same, like, alright, I guess we’re doing this now. It felt oddly familiar.
We finally went to bed, and that’s when I realized it was daylight savings time. I hadn’t been up until three in the morning in a long-ass time, and of course this was the night the clocks changed. I looked at the clock on my nightstand and it said 2:59 a.m., but I checked my phone and it said 1:59 a.m. I remember thinking, hell yes. Right when I needed an extra hour, the universe handed me one. That shit was clutch.
We’ll pick it up from there. Stay tuned for tomorrow’s entry.
If you connect with how I live and think, you can follow the rest of my days on YouTube in my Dating playlist.