This is my journal entry from December 11, 2025, part of my daily autobiography Divorce Day — my real, unedited days, published in order.
I started the day by dictating the entry for yesterday and finishing up my letter. I dropped the kids off at school, and an older friend came over to work on his book for a couple of hours. After that I went to a yoga instructor’s Yoga Flow class. It was nice to see him again because it had been a little while.
After class I chatted with a guy who had gone through a divorce with the same judge I’m about to have. His experience with the judge was very negative, although his divorce was confrontational. It reminded me how relative our points of view can be. My ex-wife has a positive opinion of the judge we’re going to have. This guy, on the other hand, had a horrible experience and felt the judge was unfair to men. I’m curious to see what my own experience will be next week as we finalize our divorce.
After yoga I went home, had a nice salad for lunch, and started getting my books ready. I printed around a hundred copies of the letter, took all the books out of my car, and reorganized them so they’d be easier to give away. Now that I’ve got the letter finished and everything prepared, I’m committed to giving away as many books as possible. I figured the best place to start would be the little free libraries where I’d previously dropped off I Was Famous on the Internet. Then it hit me that if someone doesn’t know me, the best book to leave is probably Author in St. Petersburg. The title immediately tells people it’s local and relevant to their area. That feels like a much clearer hook than I Was Famous on the Internet, which doesn’t necessarily matter if the person doesn’t realize the author lives nearby.
So today I drove around and hit about ten little free libraries in my area. I worked my way around my neighborhood and down by a nearby meeting I used to attend. Dropping those books off felt really good.
I also texted the girl from yesterday. I let her know that today was going to be the last day of the meeting and that we’d deleted it. She replied, “Thanks for letting me know,” and didn’t show up. Meanwhile I spent some time today reading Dating Essentials for Men by Dr. Robert Glover, and it’s becoming obvious that I’m doing some things inefficiently with dating, to say the least.
This morning I also got a message back from a massage therapist. On Saturday at 8:13 p.m. I had sent her a one-line message that said, “I keep thinking of you tonight and hope you’re doing okay.” This morning, she sent back a long paragraph that filled my entire phone screen. I replied with a paragraph of my own suggesting she could come do a book with me and exchange massage here in St. Petersburg. As of now, around 10 p.m. while I’m recording this, she hasn’t responded. It has me thinking, damn, I feel like I’m not doing something right with texting girls. I realize I probably need to learn how to text women better because when I was dating before, we didn’t text much at all. That was fifteen plus years ago, and back then you mostly just called women on the phone and figured out a time to meet. There weren’t endless messages going back and forth.
I also reflected on a life coach after she came over yesterday for her book session. She was very warm. Yesterday she texted me when she was on the way, and a few hours later she sent another message thanking me for the session. I had already told her when I was available, so she said Sunday would work for a coaching session. I gave her some time options for Sunday and Monday. She confirmed and gave me her address. I replied, “Wonderful, see you Sunday.” A couple of hours later she messaged again saying yes please, and I responded. She asked how I was doing after the book recording, then sent another message. I replied once more later that night. Today we haven’t texted at all, and I’m thinking I probably should have just let her last message hang there instead of replying again.
It is nice to have some space because I can see clearly the insecurities I have as a man. I notice the dependence, the desire for constant approval, and the wanting of attention from a woman all the time. Yet I also think back to a woman I was briefly involved with from massage school. She was texting me all day long and I really disliked it. Eventually I told her directly, “I don’t like texting back and forth all day, every day.” Then I look at how I’m texting now and it makes me laugh at myself.
Today I also got a message from a friend. Looking back at our history, I had done a life coaching session with her and sent her my book. After that I texted her on October 4 and October 19 and didn’t get a response either time. Later I saw her at an event and everything seemed fine. Then on Thanksgiving, after not texting me for over a month, she sent a generic message saying happy Thanksgiving to all my family and friends. I didn’t reply to that. Now about two weeks later she texts again and says, “Hey, Jerry, how are you?” I replied, “I’m doing great. Thanks for asking. I’m going to a local spiritual community and we’ll be at the dance party Saturday. What’s new with you?” She sent her message at 3:55. I replied at 4:48. Six hours later there was still no response. Sitting there looking at my phone, I’m thinking, man, I need to learn how to text girls. I’m definitely seeing that there are things they are doing, but there is also stuff on my side. My texting game needs work.
When I look back at what the dating advice says not to do, I can see several examples. When I met a woman a couple months ago, sending her a voice memo inviting her to something the very next day after meeting her, especially after she had already said she wasn’t available to date, was way over the top. Of course, she responded by saying she wasn’t available to see me one on one for the next couple of months. I had basically sent this desperate, needy, over the top response, so of course that was the outcome. The same thing happened with another woman I met. My message was too enthusiastic.
None of it is personal, yet it is still difficult because yes, people are going to do whatever they’re going to do. At the same time there are ways to present yourself as your best self and come across as confident. When I step back and look at it, I’m a little disappointed in myself. I ask, why am I acting so insecure, needy, and desperate for attention from women when part of me genuinely feels like this confident guy who has so much to offer? Then I think about yesterday, getting that girl’s number at AA and fumbling it. I got these lukewarm responses from her even though she clearly liked me. I talked with another guy at the meeting yesterday and today, and he said she looked desperate for a man. Even with that, even with me having confidence and her clearly being interested, I still managed to flub it.
At the same time I remind myself that learning what not to do is valuable. What I really appreciate is how quickly I’m making progress. It has been three months or less. Actually less than three months. September 11 was three months ago, and thinking about that is almost shocking. Back then the divorce was not even on my radar. I had just been two days into massage school. In these three months I’ve been practicing and refining the details of my dating game.
Now I’m also thinking ahead to the life coaching session on Sunday. Part of what I’m considering is whether, if I want to date her, I should make that move. I don’t want to be inauthentic or pretend that I only want to be her friend. Sure, there might be a friendship and maybe we work together on a book, but I also definitely want to escalate if possible. I’m curious to see how that goes.
There is a lot of curiosity in my life right now, and that feels healthy. I’m genuinely curious to see how things progress. I’m also proud of how quickly I learn. Tonight I downloaded three books on Amazon Kindle Unlimited because I realized I need to improve my text game. When I say text game, there is unfortunately a certain aspect of playing the game and learning how to interface smoothly with other human beings. I want to be able to text in a way that flows naturally and doesn’t put women off.
Looking back at today, I probably could have handled things with a massage therapist differently. Instead of sending a long message, I might have just replied with something simple like, “Hey, thanks for replying.” From there I could have escalated it in a straightforward way, maybe something like, “I’d love to schedule a massage with you and catch up.” Something simple. I could have asked when she might be free and suggested we get together. That would have been the moment to bring up something like doing a book together or even inviting her to come up to St. Petersburg. Long texting letters just aren’t that effective.
At the same time, I did enjoy getting the massage therapist’s long message. It was actually really nice to read. It showed enthusiasm, and I appreciated that. Maybe I’m overanalyzing things. Maybe she did enjoy receiving my message today. There’s a lot to think about when it comes to texting. It’s interesting how that short message I sent the other night ended up producing such a long reply from her today. Her message was great. I genuinely enjoyed reading it, and it was nice to see her enthusiasm. Naturally I responded with a long message back.
Then afterward I found myself thinking that maybe I shouldn’t have sent such a long reply. Sometimes when you send someone a long message it can feel like a bit of a burden for them to respond. At the same time, if a woman sends me a long message, what I really want to do from there is escalate things toward meeting in person. What I learned from the girl at massage school is that I do not want a relationship based on texting. I want a relationship based on seeing each other in person.
I took a lot of notes today because I’m noticing there are definitely some things I’ve been doing ineffectively. There are ways I could approach this that would make dating more fun and less stressful. Less anxiety, less nervousness, more confidence, more enjoyment. I can see situations where I probably could have made out with a woman I was really attracted to, and that could have been a lot of fun.
It’s interesting because women sometimes say they want a guy to ask before he kisses them. Yet when I think about my massage therapist, she’s been dating a guy for a couple of years now and seems very happy with him. When she told me the story of how things started, he actually just went for a kiss. She avoided it the first time and didn’t want it. After that he kept pursuing her and eventually asked for a kiss at a slightly awkward moment later. Everything still worked out. My massage therapist would probably tell you she prefers not to have guys lunge at her, but the guy she ended up choosing did exactly that.
It reminds me that what people say they want and what they actually choose can sometimes be very different. As a man it also takes confidence to be willing to risk rejection. Most of the time when I’ve gone for a kiss I haven’t asked permission first. I’ve just gone for it, and women often respond positively to that confidence.
I think back to dating my ex-wife. The guy she was seeing at the same time as me was probably more compatible with her in many ways. But I was confident. I walked her to the parking garage with every intention of kissing her and zero intention of asking if I could. We had already escalated physically before that moment, so it wasn’t something that came out of nowhere. It was our second date, and there had already been plenty of physical touch along the way. I had tested things at smaller levels first.
When we got to her car, I put my arm around her and confidently went in for the kiss. We ended up having a fantastic makeout session in the parking garage. That was something the other guy never did. And honestly, I don’t want to be that other guy who stands around hesitating, scared to make a move and missing the moment. Much love to him and I hope he’s had a great life, but I don’t want to be the guy who pussyfoots around and is too afraid to go for the kiss.
I’ve lunged for a kiss before and not gotten one. It didn’t kill me. The first time I remember was in high school. I spent the whole day with a friend at King’s Dominion. I already knew she either had a boyfriend or might have been dating someone else. At the end of the day, I tried to kiss her and she just put her hand on my lips and said something like, “Let’s just be friends.” At the time I got so butthurt about it. Looking back now, though, why not try?
Another thing I’m noticing is that I want to focus more on male friendships. For the first time in a long time, I’m remembering how important male friendships are. Lately it almost seems like I’ve been overemphasizing friendships with women. When I look honestly at that, it almost feels like I’ve been trying to emotionally cheat or get the validation from other women that I wasn’t getting from my ex-wife. That’s not what I want to do. I definitely don’t want to keep doing that.
I was reviewing some of the notes I took from a book today, and one point was to always suggest a specific day and plan when asking for a date. Looking back, I’ve been weak about that lately. I’ve asked a couple of women to do things without giving a specific time or clear plan. Sometimes I didn’t even suggest something exclusive. Another point that stood out to me was that if you message someone and there’s no response, you just move on. I messaged the woman from yoga and didn’t get a response. Fine. Move on. There’s no need to spend any more time thinking about it.
I did enjoy Dr. Robert Glover’s framework in Dating Essentials for Men. He talks about testing and escalating. Level one is simply conversational interest with anyone. You see if there’s basic engagement in the conversation. If there isn’t, you move on once the conversation dies because there’s no point forcing it. As he puts it, conversational energy with someone will either be high or low. If it’s low, move on because you’ve got things to do.
If the conversational energy is high, you can move to level two. That’s playful teasing, chemistry, joking around, blurting things out, talking about commonalities. If that level is going well, then you move to level three for dating. That’s where you ask for a phone number, suggest a date, or go for a kiss depending on the situation.
He also says that on a first meeting or first date you usually wouldn’t go for a kiss unless you’re trying to hook up and have sex. I’m not sure how I feel about that anymore. Thinking about a couple of girls I talked to at a local spiritual community, it feels like I may have talked too long without escalating. Those conversations essentially turned into dates. Either I should have wrapped things up earlier and gone home, or I should have gone for a kiss.
Looking back at a woman I met in particular, I think she was giving me a lot of positive signals. If I could do that moment again, when the emotional energy peaked I would definitely ask her for a kiss. I remember the exact moment and I completely waffled on it.
It reminds me how afraid people are of rejection. At the a local spiritual community shop meet tonight some people were talking about how scared they are to put their work out there and risk being rejected. I’m actually very comfortable with that part. I give my books away all the time and I’m not afraid to put my work into the world.
What people often don’t consider is how bad it feels not to go for something. To me that’s the worst outcome. You should almost be more afraid of being a wimp and not taking the chance. With that woman there was a perfect moment when we were looking up at the stars. It was incredibly romantic. I could have simply looked at her and said, “You know, I wish I could kiss you.” The moment was right there. I knew I wanted to say it, and I didn’t because I was afraid of getting rejected.
In reality, saying that would have shown confidence and it would have been appropriate for the situation. We had already built up the conversation for it. There had been physical touch and clear chemistry. She might even be dating me now instead of the other guy if I had gone for that moment. That’s also where the abundance mindset comes in. There are tons of women out there.
At the same time, I’m taking notes for the future. I was really into her, and yet I didn’t go for what I’m capable of going for. I got a 13-year marriage with my ex-wife because I went for it. It’s funny to be relearning these skills because at one point I had them mastered. When I went out with my ex-wife, I nailed that second date kiss and everything leading up to it. The dating profile worked, I got the date, and I navigated the whole process successfully. Now it’s strange to find myself remembering things I learned 15 years ago that I once had down cold. Back then I was making out with women on dates. Your boy was getting all kinds of kisses. That was normal for me. It’s time to start going for it again.
Even with the girl from massage school who came over, I remember lunging for a kiss at least once and asking to kiss her a couple of times before we ended up having sex. Looking back, that actually makes a lot of sense. That’s how you show confidence. You go for it.
Another note I took from the book was to hold eye contact longer than is comfortable with women and then look back again soon, but not stare or leer at their body. That made sense. Yesterday the girl at the meeting was giving me strong eye contact, and I noticed myself backing down a little bit. Another note I wrote down was to assume attraction. Yesterday I knew that girl was attracted to me. I knew it. Yet I was still acting nervous and scared, as if I was doing something wrong. I’m not doing anything wrong. This woman is clearly open to meeting someone and seems to want someone to approach her. She’s navigating a lot in her own life right now and is clearly looking for connection.
So why am I acting like I’m not much of a catch or like I’m doing something inappropriate? That’s something I can correct. What I appreciate is that this is exactly the kind of inventory I’m doing through the AA step work. I’m looking honestly at what happened and thinking about how I can adjust next time. Mentally I can see the correction already. Bring the confidence forward. Go for it.
Another note I wrote was to keep texts short, ideally under 20 words. If there’s a lot to say, it’s better to move the conversation to a phone call or meet in person. With a massage therapist, the ideal move probably would have been to set up an in-person meeting. Her message showed real interest in catching up with me. There’s no reason I couldn’t have scheduled a massage and driven down to see her. That would be far better, especially once my divorce is officially finalized. We could catch up properly in person. Sending a long text was probably too much too fast.
At the same time, it’s funny because I really enjoyed receiving the massage therapist’s long message. She took five days to reply, though. Sometimes patience is required. Maybe I wake up tomorrow and there’s another message from her, either a long enthusiastic one saying she’d love to come up or a short message saying yes, she’d like to do that and asking when we can start.
Another reminder I wrote to myself is not to be too hard on myself or look at every situation like it’s a win or lose outcome. Looking back at my ex-wife, it’s possible that if I hadn’t been so confident and hadn’t gone for that makeout session in the parking garage, maybe the other guy would have ended up with her. Maybe I would have ended up with someone who was more compatible with me in the long run. At the same time, I loved my marriage with my ex-wife. I wouldn’t undo any of it.
Still, it’s interesting to consider that the super confident, pushy approach sometimes wins because you’re better at dating, not necessarily because you’re the better long-term match. Yet I also know what I want. I do want to make out with women. I do want to have sex with women. If that’s what I want, then it makes sense to act like it.
If you connect with how I live and think, you can follow the rest of my days on YouTube in my Life playlist.