This is my journal entry from October 17, 2025, part of my daily autobiography Learning to Live Alone Again — my real, unedited days, published in order.
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Tonight I feel a bit sad and alone. I somehow managed to waste nearly an hour, which is unusual for me. I usually take pride in using my time intentionally, but this evening I’ve been drifting without purpose, uncertain of what I’m even feeling. Part of me thinks I should be out somewhere meeting new people—specifically single women—and putting in more effort to socialize. I’ve heard there are plenty of single girls downtown, at bars and restaurants, but I can’t tell if the thought of going out sounds unappealing or if I’m just scared of rejection. Maybe it’s both. Still, I remind myself that the kind of women I’m looking for are looking for me too. We’re all in this together, trying to find connection.
Next weekend I already have plans: Friday night at the tennis club and a Halloween party on Saturday. But this week I didn’t plan anything. The social at my yoga studio last week was nice, though I ended up talking to one mom for too long, as I mentioned in my last entry. Today I’ve been sneezing and dealing with a runny nose, which oddly feels like an emotional purge—almost as if something inside me is draining out.
This morning started well. I woke up with the kids and helped get them ready for school while my ex-wife was away on her trip. Her mom picked them up since my car is still at the Toyota dealership. I walked back to my house around 8:00 a.m. and passed an attractive girl walking her dog about halfway between my house and my ex-wife’s. I don’t think I’d seen her before. We exchanged good mornings, and she smiled and made eye contact—something rare and noticeable. Then she stopped to play with her dog right after passing me, which would have been a perfect moment to turn around and talk to her. But I didn’t. I kept walking home like I was on autopilot, almost like a Tesla set to drive itself.
When I got home, I thought about it. That moment could have been something. A beautiful girl in my neighborhood—that would be ideal for dating, even better if we hit it off enough that I could move in with her one day. It would be incredibly convenient. That’s top-tier dating strategy right there: local, easy, natural. Yet I just walked right past the opportunity.
Later, while listening to Models by Mark Manson, I realized what I could have done differently. I should have just been authentic in the moment, not rehearsed or strategic. All I needed to do was extend the conversation naturally after saying good morning—something like, “Wow, I don’t usually see a beautiful woman out walking her dog alone this early in the morning around here.” Maybe follow that with, “You probably already have a boyfriend at home, right?” If she said yes, I’d know where things stood. If not, I’d have a real chance to connect, get her number, and see what kind of compatibility there might be. At least then I would have known instead of wondering.
Reading Models reminds me how essential it is to be direct about what I want and what I’m looking for. For years I’ve thought of myself as an honest person who says exactly what’s on my mind, yet I can see now that with women, I haven’t been nearly as straightforward as I believed. It made sense while I was married—of course I wasn’t walking up to attractive women and telling them what I really thought. But it’s wild to notice how thoroughly that pattern of self-censorship has stuck.
If I were being completely honest over the years, there are plenty of times I would have wanted to walk up to a woman and tell her exactly how attracted I was. Obviously, that wouldn’t have been appropriate as a married man, but recognizing that instinct is revealing. It’s crazy how easily we can get conditioned to behave in ways that aren’t fully authentic—not because we’re lying, but because we’re following what seems like the “right” thing to do. Looking back, I see how often I suppressed attraction or defaulted to shallow, friendly conversations, convincing myself that was the moral path.
Now, I see it’s time to change. I want to start being direct again—saying things like, “You’re beautiful. I’m wondering if you’re available to date.” That’s not manipulative or crude; it’s honest. I actually talked about this at length in the second part of my dating book. This realization fired me up this morning. I don’t want to miss any more opportunities. I believe the universe is constantly trying to deliver what we desire, and if we’re open to receiving it, it arrives easily.
Since becoming effectively single—though still technically married and in the process of divorcing—I’ve noticed attractive women appearing in my path almost every day. Yet not once have I directly asked if one was single or complimented her openly. I’ve played it safe, hiding behind politeness. That’s about to change. I’ve always thought of myself as someone who handles rejection well, but in dating, I’ve fallen out of practice. It’s time to rebuild that muscle.
After reflecting on all this, I felt motivated to keep working on The Kind Divorce. I finished editing it last night, and now all that’s left is to polish it up, create the Amazon listing, and publish. Before that, though, I wanted to go to my yoga instructor’s 9:00 a.m. class at my yoga studio. Without a car, I decided to walk the twenty minutes from my house to the studio and made it just in time.
Surprisingly, there wasn’t anyone in the class I felt drawn to approach romantically, but I did see a friend I’ve known for years who’s been gone for a while. She smiled and waved, and it felt good to see her again. Another friend was there too. She’d mentioned yesterday that she wanted to talk about my book, so I figured I’d ask her for a ride home afterward. It seemed like the perfect way to connect.
The class itself was a solid workout, and by the end I was drenched in sweat. Afterward, I said hi to a friend and then asked another friend if she could drive me home. She said yes, which I appreciated—not just for saving the walk, but for the chance to talk. During the ride, she shared her thoughts on I Was Famous on the Internet and opened up about her own personal growth and challenges. Listening to her talk about character building and the lessons she’s learning made me feel genuinely connected. When she dropped me off, she gave me a hug, and I realized that was the best I’d felt all day.
After the workout and my conversation with another friend, I felt a surge of creative energy and decided to go all in on my books. I’ve been thinking about how to organize and title all these diaries, and last night the idea came to me—Jerry’s Journals. This morning, I brainstormed alternatives and went back and forth with ChatGPT for a while before ultimately deciding that Jerry’s Journals was perfect. It captures the essence of what I’m doing: documenting my real life in an ongoing, unfiltered series.
The plan is to have Author in St. Petersburg as the first book in Jerry’s Journals, followed by The Kind Divorce, and then this current volume as the third. The concept excites me because anyone who discovers one book in the series might naturally want to read the others, tracing the full story of my life as it unfolds. I want these books to function as a living autobiography, one that grows with me over time. In a way, this project might end up being my greatest teaching—not advice or theory, but a transparent record of what I’m actually doing day to day. I’d personally rather read that kind of book than another self-help manual filled with abstract concepts. So I’ll lead by example.
Between 10:30 a.m. and 1:30 p.m., I get a ton done. I have hummus for lunch, finalize The Kind Divorce, and set up its Amazon page. I also record around forty minutes of new material for my dating book, covering the events of the morning and what I learned from Models. On top of that, I dictate yesterday’s diary entry, since I hadn’t had time to do it before.
Later in the afternoon, the Toyota dealership finally calls to say my car is ready. I ask whether I can get a shuttle or if I should take an Uber, and after about two hours of waiting, the shuttle shows up. At first, I think there’s a hot girl sitting in the front seat—I notice a pair of legs through the window—but as I get closer, I realize they belong to a man. Clearly, I still have some work to do getting my vision back to 20/20.
The van is quiet at first, so I take it as a chance to practice conversation skills using some of Mark Manson’s advice from Models: make more statements instead of firing off endless questions, and focus on creating a genuine back-and-forth flow. I start talking with the guy in the front seat, whose name is a man I met in the dealership shuttle. He tells me he’s in the middle of his second divorce and has two children—one from each marriage. He says he really loved his first wife but things eventually burned out, while his second marriage has been much more turbulent. The divorces, he tells me, have cost him close to a million dollars.
Listening to him makes me feel grateful for how my own situation with my ex-wife is turning out. She’s actually giving me some money in the split, which is a rare gift in itself. We have a solid fifteen-minute conversation during the ride, even as my mind keeps critiquing the shuttle driver’s habits—reminding me why I prefer to drive everywhere myself. Still, we arrive safely, which is what matters most.
At the dealership, the service advisor helps me check out. I notice a $200 diagnostic fee still on the invoice and ask him to remove it, since I’m already paying $1,300 for the repair and there’s no reason to double-charge for the same work. He agrees, removes the fee, and I pay the $1,300 on my credit card. I feel genuinely grateful to have my car back. The air conditioning is running perfectly again thanks to the new radiator cooling fan, and as I drive home, it feels like I’m in a brand-new car.
Right after I get home, I know my ex-wife will be back with the kids in about twenty or thirty minutes, so I plan to head over as soon as she arrives. But as the time approaches, a feeling of sadness begins to creep in. I realize I’m not actually excited to see her. The thought of getting only a friendly hug instead of the kind of warmth and affection I used to feel when she came home from a trip leaves me uneasy. It feels like something essential between us is missing now.
I decide it’s probably best to give her some space to unwind and spend time with the kids before I come over. After waiting about fifteen or twenty minutes, I walk down the street, say hi, and give her a brief hug. I talk to the kids for a few minutes since I haven’t seen them since they left for school that morning, and then I head out again for my AA meeting.
There are eleven of us at the meeting, which feels like a solid turnout. I bring up the topic of dealing with resentments, something that resonates with several people in the room. Toward the end, there’s an awkward minute or two of silence when no one wants to share. The woman who read just before me starts talking about being open to receiving a spiritual awakening, and it gets me thinking about openness in general—especially physical openness. I look around the room and notice that about half the people are sitting with their arms crossed, which to me reads as closed-off body language.
When it’s my turn to speak, I talk about how our physical posture often reveals more truth than our words. I mention that if we say we’re open but sit with our arms crossed, we’re sending a conflicting message. I add that I try to stay aware of my own body language—where my arms, legs, and hands are—and that if I can’t genuinely open up in a space, it’s probably better for me to leave rather than pretend. My comments clearly hit a nerve. A few people shift uncomfortably and uncross their arms, and the energy in the room turns a little defensive. Some take it personally, even though I’m just sharing what I see. Before long, the tension rises enough that we wrap up the meeting a few minutes early.
Afterward, I chat with one of the women there, someone I’ve always liked talking to. She’s attractive, kind, and we’ve had a good rapport over time. Last I heard, she was single, though she used to date one of the guys I’m close with, and that didn’t go well. I feel a bit confused about her—partly drawn, partly hesitant. I’ve invited her to hang out outside of meetings a few times, but she’s never followed through. She says things that suggest she likes me, but I also know some of her issues, and deep down I suspect we wouldn’t be very compatible.
As I leave the meeting, I wonder if that feeling of lukewarmness—of neither real excitement nor deep connection—is its own kind of clarity. Maybe that’s how I know she’s not the right one for me.
I drive to my son’s soccer practice feeling sad and confused, hoping that talking to my ex-wife might help. When I sit down beside her, we start an easy conversation about everything—her trip, my feelings, our future, the kids, even dating. The talk flows naturally, and by the end of it I feel lighter. We share several laughs and inside jokes, which feels comforting. It reminds me that even though our marriage is ending, there’s still warmth between us.
I make a point to really appreciate these moments, knowing that once I start dating someone else, there may be fewer chances for conversations like this. The thought even crosses my mind that, despite my ex-wife saying she isn’t interested in dating, she might still end up seeing someone first—or even just hook up with someone before I do. That idea stings. Still, I remind myself that she’s not mine to possess. That was one of the biggest problems in our marriage—the way we tried to control each other and shape one another to fit our own desires. Marriage doesn’t make a person your property; it’s supposed to be a partnership, not ownership.
When my ex-wife mentions she’s changing her plans for the night, I notice how my reaction has changed. In the past, I would have had an opinion—probably told her what I thought she should do. Now, I just listen and acknowledge it. She’s an adult living her life, and I don’t need to comment or manage her choices.
As evening sets in, I wish I had plans. I even consider going downtown, parking, and walking along Beach Drive just to see what happens. But the thought terrifies me. It feels inefficient, like a waste of time. I tell myself I have books to record, projects to finish. Then again, dating has been on my mind constantly, and maybe putting myself out there would help—and could even make my dating book more interesting.
The big obstacle is sobriety. I don’t want to be surrounded by drunk people. Many of the women downtown might not be alcoholics, but I also don’t want my story to start with “I met her at a bar.” It just doesn’t feel right. I’d rather meet someone close to home, maybe through yoga at my yoga studio, tennis, or an AA meeting—places where I already belong. Women I meet there are more likely to share my values and lifestyle. Plus, it’s practical. A woman I meet downtown might live fifteen or twenty minutes away, or even across the bay in Tampa, and I’d rather date someone in my own neighborhood.
Meanwhile, I’m feeling excited about my next creative chapter. With The Kind Divorce nearly ready to publish—just an hour or so away from final submission to Amazon—I’ll soon have some open space to begin my first fiction book. That thought fills me with energy. I see how important it is to stay inspired by what I’m creating, to channel all this emotional intensity into my work rather than let it drain me.
The idea of spending my night trying to meet women in a bar feels false. That’s not where my authentic self thrives. So I start separating in my mind what I think I should be doing from what truly feels right. I look up local events and realize I’ve missed a good one tonight—a kirtan ceremony at a local spiritual community here in St. Petersburg. It ran from 6:00 to 10:00 p.m., and it would have been exactly my kind of scene: spiritual, communal, probably full of women aligned with my energy. I simply hadn’t planned ahead.
Now I know better. I’ll start keeping an eye on things like that so I don’t miss them again. I already see that another kirtan is happening on Friday, November 7, and I plan to be ready for it. It feels good to set that intention—to take this sadness I’m feeling and turn it into purposeful, productive action.
Next weekend is already shaping up to be full. I’ve got Friday and Saturday night both planned, and the weekend after that, if I go to the spiritual community’s kirtan ceremony, I’ll have both nights filled as well. It feels good to have some structure again—to see that what I’m learning is I need to intentionally plan nights out around things that truly fit me.
The kirtan ceremony, for instance, is listed as a sober event—no drugs, alcohol, cannabis, or psychedelics. That alone tells me these are my kind of people. It’s the sort of “sober container” I want to be part of, a space where people are present, grounded, and not trying to escape themselves.
I actually have a scheduling conflict next Saturday: there’s a Halloween event at the spiritual community I’d love to go to, but I was also invited to an AA party. I decide I can probably do both. The AA event starts at 5:00 p.m., so I could stop by, see if it’s lively, and if it’s not “hopping or bumping or banging,” as people say, I could leave around 6:00 p.m. and head straight to the spiritual community’s Halloween event. That would actually be perfect—socializing in both of my worlds, the sober community and the spiritual one.
As I think about all this, I start to feel genuine happiness returning. Sometimes sadness hits when all we can see is what’s missing—our mistakes, the gaps in our lives, the things that aren’t working. Tonight, I can see how focused I’ve been on lack. I’m acutely aware that I don’t currently have a woman I’m sleeping with or cuddling with, someone I feel real mutual attraction for. That awareness itself is painful. But it’s also a signal: it’s showing me what I want more of.
At the same time, I know there are probably a hundred women in this city who would love to fill that space if the timing and chemistry were right. Thinking of it that way brings me joy. I just need to start showing up in the places where those kinds of women are—events like kirtan ceremonies, sober gatherings, the spiritual community’s parties. Those are my environments, and those are the women who will naturally align with me.
Now, with two full weekends of plans ahead, I’m starting to feel grounded again. Life starts to make sense when I take small, intentional actions instead of sitting around feeling stuck. Sadness doesn’t always mean something’s wrong; often it’s just a call to act, or at least to open my mind. It’s a signal that something needs attention—whether that’s making new plans or simply accepting where I am. If I’m going to spend Friday night home alone, I can either feel sorry for myself or embrace it: enjoy the peace, work on my books, and be grateful for the quiet. Or, I can choose to get out there and engage with life. Either way, it’s about ownership.
Next weekend is looking solid, and even tomorrow night might bring something good. There’s a drone show at Vinoy Park that I could take the kids to, which would be perfect. It’s nice to have that option and to see my life taking shape in a balanced way—time for work, time for the kids, time for myself.
I feel genuinely grateful for how much I’ve accomplished today. I’ve spent over an hour and a half dictating new material, plus several more hours editing books. I love this work. I could easily see myself doing this full-time—writing books all day and connecting with one or two people personally, either to monetize what I do or simply to spend time with readers who genuinely resonate with me. That would be the ideal rhythm: deep creative work paired with meaningful human connection.
After soccer practice, my ex-wife and I stayed to watch my son play at the park for about thirty minutes. I sat on the merry-go-round while a little girl around my son’s age started pushing me and chatting away, full of energy and curiosity. After a few minutes, her mom called her back sharply, telling her to return to the family. For a second, I felt a flicker of rejection, like I’d done something wrong, but I reminded myself not to take it personally.
My son was busy climbing over the rock wall, proud to tell me he’d made it across ten times. I felt that familiar parental twinge of fear, worried he might slip and fall, even though I know most of those fears are overblown. It’s funny how the things we don’t even think to fear often happen without consequence, while the ones we worry about rarely do. I remembered when my son was at a relative’s house a few years ago—he was running around, and one of the dogs crashed into him. He hit his forehead on the concrete wall right on the crack. My aunt panicked, but my son barely flinched. He got a huge lump on his head, but it healed fine. That’s parenting in a nutshell: constant worry over things that often turn out to be no big deal. I’m just grateful he played safely and had fun at the playground today.
Afterward, we stopped by my mom’s house for about twenty minutes. The kids and I shared an Oreo ice cream sandwich, and I had a bowl of her travel-sized Apple Jacks from my brother’s wedding hotel stash. Then we walked back across the street to my ex-wife’s house, where I made the kids popcorn.
Even though I was feeling weighed down by sadness, I decided not to rush home. I stayed, soaking in the time with the kids, cuddling up with them as much as I could before bed. I figured, someday when I do meet that girlfriend who wants real intimacy and affection, she’ll probably appreciate if I’m not spending a couple hours at my ex-wife’s house every night. So this is the time to enjoy it—to take full advantage of these evenings when I still get to tuck the kids in and feel their little arms around me.
My son and I snuggled in his bed. He was trying to “juice” me as usual, our word for wrestling around and laughing. I tickled his belly until he couldn’t stop giggling. Before leaving, I helped my ex-wife with the toilet, which had clogged again. It was a tough one this time, but I used some bath water to refill the bowl, and that gave it enough pressure to clear.
After saying goodnight, I drove over to Whole Foods and called my sponsor. I sat outside at one of the tables, talking to him for a while. Part of me hoped maybe I’d run into a single woman—a mom or someone shopping alone late at night for a pint of ice cream to eat while feeling lonely, or maybe picking up a salad like I was about to. Something about Whole Foods at night just felt like the place to be, though the crowd was thinner and less attractive than during the day.
When I finally went inside, I grabbed a basket and stopped near the lettuce section. Just then, one of the guys I know from AA walked in. It felt almost orchestrated, like some small twist of synchronicity had brought us both there. He said he’d just finished playing hours of role-playing games with friends and was grabbing a bite before bed. I laughed and chatted with him for a moment, thinking afterward that I should’ve told him my real reason for being there—to see if I could meet a woman at Whole Foods. Maybe next time I’ll be that direct.
As I wandered the aisles, I noticed a couple of attractive women shopping together, but one looked so young it gave me pause. I realized it was probably a mother and daughter, and they didn’t glance my way anyway. I took that as a gentle sign from the universe that it wasn’t the right moment—or the right direction—to pursue.
I check out at Whole Foods with a basket that makes it clear just how healthy I eat: five avocados, two containers of salad lettuce, bananas, cooked beets, vegetable slaw, and celery. It’s definitely some woman’s type—but probably not most. Still, my body loves this way of eating, and I feel great when I stick to it.
Back at my place, the sadness hits me again. I sit on the couch feeling hollow, and my mind starts taunting me—telling me I’m lame for doing this, for being alone, for not having someone next to me. I grab my phone anyway and redownload Bumble and Hinge, just to confirm they’re still a complete waste of time. On Hinge, I don’t have a single like or match. I delete it immediately. On Bumble, I still have the one like from before, but it’s not from anyone I’m interested in. Another reminder: dating apps are not the path forward for me.
I’ve put so many hours into swiping, and I’m done wasting time on women I’ll never meet—profiles that may not even be real, or that were created months ago by women who’ve already moved on to other relationships. My profile is honest and well done; even my ex-wife said so. But clearly, the energy there just isn’t right. The whole experience feels dead and disconnected.
I realize I’m putting out a frequency tonight that’s tinged with sadness, quietly hoping someone will comfort me. Part of me imagines a beautiful woman walking by at nine o’clock at night, stopping to say hello—like the girl walking her dog this morning. Instead, my phone buzzes with a text from my mother. She says she’s walking right by my house.
I actually laugh out loud, glad I’m completely free to see her right away. My mom hasn’t been inside my new house yet, so I invite her in. She looks around, smiles, and says it’s perfect for me. She reminds me that if I ever want to come over, watch a movie, or just talk, she’s there. I appreciate the reminder more than she probably realizes.
It also strikes me how aligned the night has been. Earlier, I thought it’d be nice if something pulled me to Whole Foods—and it did. Then I thought it’d be nice if someone stopped by to see me—and my mom texted right after. She’s never done that before in the week I’ve lived here. To me, it feels like a little wink from the universe, another reminder that we’re all telepathically connected in ways we don’t always understand.
As I sit reflecting and recording, I can feel my mood shifting upward. I’m grateful for the ability to write these books, to document these moments as they unfold. Whatever this book becomes, I’m excited for it. I wrap up my notes for the night, take a shower, and get ready for bed—thankful for the small signs that everything is still working out exactly as it should.
If you connect with how I live and think, you can follow the rest of my days on YouTube in my Dating playlist.