This is my journal entry from October 31, 2025, part of my daily autobiography Book 5 — Daily Autobiography — my real, unedited days, published in order.
More mind expansion today. I actually went out tonight and walked through a bar with my friend who’s been sober in AA longer than I’ve been alive. Earlier in the day he was encouraging me, telling me straight up, you need to get out and meet girls, and that’s where they are. You can stay sober. Most of them aren’t alcoholics. They’re just out at bars hoping to meet someone. He invited me to go out with him to the Vinoy, so we went over there, checked out the new restaurant, looked around at all the beautiful women, then drove down Beach Drive. It wasn’t super active tonight, probably because it’s Halloween and a lot of people are at private parties, but still, it got me fired up. It felt like, yeah, this is what I need to be doing.
He also gave me some solid advice. If you’re going somewhere with alcohol, don’t go alone. Always go with someone else. It lowers the chance you’ll drink, lowers the chance you’ll do something stupid. I asked him why I couldn’t just go by myself, and he said because when you’re alone, the odds go up. You might pick up a drink. You might get roofied. I was like, roofied? He said yeah, it’s happened to him more than once. You ask for a virgin daiquiri or some shit and there’s alcohol in it anyway. That stuck with me. I also thought about this guy I know in AA who hooks up with women at meetings all the time, and then goes home sad and alone afterward. That guy needs to be out in the real world too. Honestly, he should be out with me. We’d make great wingmen together.
What really hit me tonight is that I want to have more fun. I don’t know if I’m ever going to meet some amazing woman and build another family. I hope so. I genuinely believe it’s possible. But what a complete fuck-up it would be if I took this super serious, borderline religious approach where I’m “saving myself” for some hypothetical future woman and end up just being lonely and isolated every night instead. That’s not noble. That’s sad.
And that ties into something that happened earlier today. I was looking for speed dating events or Tantra events because I had nothing planned tonight or tomorrow and thought, I need more stuff on my calendar. I started looking around and found these women offering private Tantra sessions — one charging a few hundred dollars, another over a thousand for a two-hour “masculine-feminine intimate experience.” And I’m sitting there like, are we just talking about sex work? Is that what this actually is?
So I called a friend of mine from AA — the same guy I was thinking could be a good wingman — because he’s dealt with sex addiction and I figured he’d know. I asked him straight up. He laughed and said yeah, most of the time it’s basically a paid sexual service dressed up in nicer language. And hearing that snapped me back to reality. I’m like, that sounds awful. I’d feel ridiculous paying over a thousand dollars for that, and sketchy as hell sending my information to someone who might just be running a scam.
And that was the real wake-up moment. The fact that I was even considering paying that kind of money for that kind of experience told me something important. It told me I’m not meant to be sitting at home, isolated, scrolling the internet, fantasizing about transactional intimacy. It told me I need to be out in the world meeting actual people, because the alternative is sad, desperate, and disconnected — and I don’t want to live like that. That realization alone made tonight worth it.
I need to be getting out and meeting more people because sitting around like this is sad and desperate. There are a lot of lonely single people in this town who’d love some connection, and honestly, so would I. Now, if this were a total sausage fest like Columbia, South Carolina in the early 2000s—where you’d walk into a bar and there were three dudes deep competing for every girl—that’d be a different story. But St. Pete is not that. We drove down Beach Drive and it was women everywhere, so many attractive women, and not that many straight guys out competing. The odds feel like they’re in my favor.
I actually put some effort into how I looked tonight too. Nice white collared shirt, black pants, belt, dress shoes, shirt tucked in. I looked in the mirror and thought, damn, I look good. I could meet some beautiful women looking like this — especially with the confidence I have when I’m not spiraling in my head. What I need to stop doing is leaning on solo habits out of loneliness. I’m thinking about easing off that unless I’m actually feeling it, which lately I haven’t been. That’s a sign. You’re supposed to save that energy for a real person.
And if that real person happens to be a fifty-five-year-old woman who’s full of life and desire, why not? If she takes care of herself and there’s a real connection there, that’s worth a lot. It’s a kind of avoidance to just sit here waiting for some perfect, imaginary woman to appear while life passes me by. That’s not patience.
I keep thinking about that single mom I met a few weeks ago. I’d already known her for about a year at my yoga studio, and that night I could tell she was interested in me—at least I thought I could at the time, though my experience with my massage therapist has made me question my reads a bit. Still, she was dressed up, going through a divorce, clearly open, and I absolutely would’ve enjoyed being with her. Instead, she went home frustrated. She spent a lot of time talking to me, and I didn’t make any move. I went home feeling this weird mix of sad, lonely, and falsely virtuous, like I’d done something noble by holding back from someone who seemed to want me.
Looking back now, that’s ridiculous. I should’ve said, hey, let’s go back to my place. You don’t have the kids, I’ve got my own place, let’s have some fun. Let’s enjoy life. Instead, I got judgmental. She drinks. She smokes weed. You can hear all that judgment in my previous diary entries. And now I’m like, what the fuck? That’s not who I want to be. What if I never meet another woman and have another relationship like the one I had with my ex-wife? Am I really going to look back on this time and be glad I sat at home alone congratulating myself for being “disciplined,” or am I going to wish I’d actually lived? That’s the question I’m finally starting to take seriously.
In that case, I want to be out living. I was with the same woman for fourteen years. Fourteen years. I’ve been craving the experience of someone new — variety, a different dynamic, life beyond one script. And lately I’ve mostly been alone with that craving, which is just depressing. The point is, intimacy is meant to be shared, not something I keep to myself by default.
There are things in life you do alone—take a shower, whatever—but there are things that are just better shared. I can take care of myself, but it’s so much more fun with another person. I can eat dinner alone, but it’s way better eating with someone else. And I’ve been getting lonely and sad. Honestly, thank God I got lonely and sad enough today that it cracked something open. I realized I need to open my mind. I need to be out. If there’s a speed dating event, I should be there. If I can show up somewhere and actually have real conversations with single women, I should be doing that.
Yeah, yeah, nobody should be into you, Jerry. That’s how on I am tonight. And I’m not going to pretend I don’t think about this — part of me is genuinely curious about my own sexuality, about what I’m actually open to. I think most people are way more sexually fluid than they admit, and that most of us, underneath it all, just want pleasure and connection. I’m more curious and less afraid of that than I used to be.
I’ve had fantasies I wouldn’t have admitted to years ago. There, I said it. Do I know exactly what I’d want? No — and a lot of it I’ll probably never act on. But I don’t judge it anymore. It’s just part of being honest with myself. What I do know is that fun and play and joy need to be primary right now.
Sitting at home, feeling sorry for myself, scrolling through women offering private tantra sessions—that’s lame. And I don’t want to be lame. There are lonely people out there who want to be wanted and enjoyed, and I want to bring that kind of connection.
Can I just point out that this sounds like the opposite of what I was saying a day or two ago? Yeah. It does. And honestly, if I just try on every different point of view long enough, maybe I’ll find one that actually fits. Because what’s really been happening is I’ve had a hard time getting honest. I’ve been in monogamy for so long that my brain doesn’t even know how to tell the truth about desire anymore. And if I’m really honest, the desire is strong right now. Can we just say that out loud without pretending it’s something more noble than it is?
And yeah, sometimes I think about trying things I’ve always written off — being more open, less rigid about labels. I’d say I’m mostly straight with a little curiosity mixed in, and I’m honestly just interested in what I don’t know about myself. The voice in my head riffs on it and cracks me up, but underneath it I really am curious about what I’d feel.
I’ve had college stories where my own hang-ups and twisted logic got in the way of being honest about what I actually wanted — and looking back, that pattern is the real lesson, not the details.
And I’ll be honest about this too. After my sophomore year of college, I went through a phase where I was privately curious about guys while outwardly throwing around homophobic jokes and performing hyper-masculinity with my friends. I even hinted at it once with a friend, in a roundabout way, and he didn’t pick up on it. The contrast between what I was projecting and what I was actually feeling is the part that stays with me.
After that, I felt rejected. So I went into full compensation mode, pretending none of that happened, pretending I wasn’t thinking what I was thinking. I went absolutely feral trying to pick up girls. I remember being at SeaWorld, up on one of those water rides where you’re riding inner tubes, and I was hitting on a lifeguard so hard she was visibly uncomfortable. I was just firing everywhere, trying to prove something. And the irony? Zero sex. No girls. No guys. Nothing. Just desperation and noise.
That’s the pattern I’m seeing now. Swinging between extremes. Trying to be virtuous one minute, feral the next. And underneath all of it is the same thing: wanting connection, wanting touch, wanting to feel alive, and not knowing how the fuck to hold that honestly yet.
There’s another old story from years ago — a night out drinking with my best friend in a town that was a total sausage fest, where we never managed to meet anyone. We came back to his place frustrated, and it led to a moment between us that I handled badly at the time.
Without getting into the crude details, he made a vulnerable, half-joking advance, and I shut it down — fine — but then I didn’t keep it to myself. I told everybody and roasted him for it. That’s the part that still makes me cringe. He didn’t even make a big deal about it, but if it had been me, I’d have been mortified. And somehow he’s still one of my good friends today. Looking back, the thing I regret isn’t the rejection — it’s that I broadcast someone else’s vulnerable moment for a laugh.
Looking back, I’m a lot less afraid of all that than I was then. Whatever might or might not have happened, it wouldn’t have been the catastrophe my younger, more homophobic self imagined. That’s really the lesson — how much fear and posturing I used to carry that I’ve since let go of.
So yeah, I’m interested in exploring, and also a little nervous, because you never fully know what people are into. I was listening today to Want by Gillian Anderson, where women submitted their anonymous sexual fantasies. And the takeaway is clear: women have just as much desire as men do. I think guys grow up picturing women as if they’re always running from sex, and it’s just not true. The women I saw out tonight got dressed up and went out hoping to meet someone and feel wanted, same as anybody. Desire is human — it’s not a guy thing.
I’ll leave it there before my brain wanders somewhere it doesn’t need to go. Y’all have imaginations. So do I. Moving on.
And I’m glad I’ve learned something today. I want to be living fully. I’m a healthy, good-looking guy, and I don’t want to spend my nights alone and checked out. I want real desire, real connection. I want to have fun, man. I was listening to a book about how the world is supposedly heading toward biological collapse, and it got me thinking — what if you knew you had two years left? I’d be living it up, laughing as much as possible, connecting as much as possible. Even if nobody ever listens to this, I’m laughing my ass off listening to myself talk. That’s a win. Even if I never find another woman to build a great family with, if I’m out living and connecting, at least we’re having a good time.
And there are lonely people out there who just want to feel wanted. My mind keeps riffing into wilder and wilder territory, and I crack myself up with it, but the real point underneath is simple: I want to explore. I want to have fun. I want to stop being so goddamn serious. Enough of this “I’m just going to wait around for the perfect woman” energy.
Honestly, I’m probably going to have to start a fourth fucking dating book because the first three have kind of gotten fucked up. It’s time to start another one that says, look—have some fun. First and foremost. Play around. Experiment. If there’s a real, consensual connection, go for it. Life can be short. What if an asteroid wipes this place out tomorrow? What if global warming hits a tipping point and the poles shift and everything goes up in flames? Have fun. Enjoy yourself. We have to have fun. I’m tired of being stuck in this house. I’ve got a place to myself, and I’d rather be out meeting people and enjoying life than sitting here alone.
Yeah, I know — selfish prick. But the real thing I’m getting at is that so many single people are out here struggling, sitting at home lonely and sorry for themselves. The move is to get out and actually connect with people. I honestly think that would make the world a better place. I’m out here doing my part.
I went to my AA meeting today, and we had a good conversation about the second step—being restored to sanity. I spent a couple hours talking with my friend about the difference, for me, between sex addiction and just having fun. The difference is the heaviness, the trauma, the seriousness of it. I don’t want that. I just want some fun, honest connection, sober. I realized my attitude about alcohol has been too serious lately. For me, alcohol can be deadly — I know that. But not everyone out there is an alcoholic. A lot of people at bars are having a drink or two and just hoping to meet someone confident and present. That’s why they’re there.
And honestly, if I meet someone great and there’s a real, mutual spark, I’m all for it. I’m done apologizing for wanting connection and enjoying my life.
I’ll go to these speed dating things and meet some new people. I want to meet some new guys too—guys who might like my books, who might make good wingmen. To me, that’s a big part of life: get out there, play, and have fun. That’s where a lot of us as adults go wrong. Sure, there are times you need to be serious—when you’re driving, you don’t want to be swerving all over the road; if you’re a surgeon in the middle of a serious operation, you’d better be focused. There are moments where focus matters.
But the problem is, most of the time, we as adults are doing too much of that. Too much seriousness. Too much control. Too much “what does this mean?” instead of “is this fun?” And when I think about the woman I met, it really hits me. If I had gone to a speed dating thing the night before, if I had hooked up with a couple girls that week, I probably wouldn’t have been so serious with her. I probably wouldn’t have been sitting there trying to decide if she was a future wife. I probably would’ve been trying to make out with her instead of just talking and talking and talking.
I honestly think I might have been able to have sex with the woman I met if I hadn’t been so desperate. If I’d just been having fun, we might have made out at the party, at the dance at the spiritual community. Or maybe she would’ve said no—and that would’ve been fine too. Because if a girl wants it, it’s worth asking. If a girl wants to make out, it’s worth trying. I haven’t made out with anyone besides my ex-wife since 2011. That’s insane. It’s time. It’s past time.
And what if things had gone differently with her that night? Sure, it could’ve gone wrong, but it might’ve been a lot better than what I did—just talking and projecting and wanting to date her. She said she wasn’t available to date. But it felt like she enjoyed the conversation, and when I got her into that nice romantic spot and held her hand, she seemed really into it—like she was waiting for me to make a move. When I just kept wanting to talk, she seemed less enthusiastic. If I’d read it better in the moment, the night might have gone somewhere instead of me waking up the next morning over-texting after she’d already said she didn’t want to date.
So yeah, I’m feeling good today. I’m excited. And honestly, this is going to make great material for these books. Because if I just keep being boring and telling you how lonely and stuck I am every night, nobody’s going to read that. Well, maybe some other lonely bastard sitting at home like me. But that’s the thing. The difference between being a winner and being a loser is your own choices and your own judgment.
I’ve been feeling lonely because I’ve been doing lonely things—sitting at home, scrolling, isolating. Going out, meeting real people, having real connection, having fun, experiencing new people—that’s the better path. That’s fun. And yeah, I could come up with reasons not to do it. I always can. But what’s fun? What’s joyful? I’ve always been happiest when I made choices based on fun and joy, while still being considerate of other people. It’s insane for me to be sitting here alone instead.
So I’m excited to see what comes next. I’m going to book all the speed dating events—even if they’re at bars. I might go to Sarasota. I might go to Tampa. We’ll see what happens. Thanks for listening, and I’ll see you here tomorrow, or whenever the fuck you’re listening to this. Ha ha ha ha.
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