Learning to Flirt Again After Marriage

Learning to Flirt Again After Marriage

This is my journal entry from September 30, 2025, part of my daily autobiography The Kind Divorce — my real, unedited days, published in order.

I took the kids to school this morning, reading my son a few pages from his newest space book that he’d checked out from the library before drop-off. It’s one of the little rituals I love most—those quiet, curious moments before the rush of the day begins.

When I got home, my ex-wife and I sat down for a long, beautiful hour-long talk about our future. We’re both genuinely happy with where things are heading. She’s relieved to have space and freedom again, and I’m grateful we’ve managed to build such peace into this process. She cried a little when I told her I wanted to make financial amends for all the years I’d spent doing whatever I wanted with money without truly collaborating. It felt healing for both of us—to acknowledge the imbalance and start righting those wrongs before I move forward into the next chapter of my life.

After our conversation, I went to my tennis lesson with my tennis coach at the tennis club. I walked the entire complex—all sixteen courts—before I finally found him on the first one, which he almost never uses. It had been a week since I’d last played, and it felt great to be out there again, hitting ball after ball, letting my body find its rhythm. About halfway through the lesson, I told my tennis coach about the divorce. His reaction was simple and kind—he said it sounded like we were both being really mature about it. I agreed. What strikes me now is how much that is a choice. We could just as easily make it ugly. But it helps so much that we’re both on the same page. Trying to be calm and fair while the other person is melting down would be brutal. I’m deeply grateful for how mature my ex-wife has been through all of this.

After tennis, I came home and threw myself into editing I Was Famous on the Internet again. I’d love to have it live on Amazon by this weekend. This feels like the final pass—the one that pulls everything together. My ex-wife was picking up the kids, so I had the house to myself for a bit, which gave me time to take two calls from friends that came at the perfect moment.

One of them was a friend—one of my very first readers after yoga one day at my yoga studio. I remember he wanted to buy Author in St. Petersburg and Speaker Meeting 2017. I usually give Author in St. Petersburg away, but he insisted on paying, and all he had was a $20 bill. So I told him he could take both books for $20—a buy-one-get-one deal.

He called to check on me, but also to tell me something that made me laugh. A woman had sat next to him in an open room at my yoga studio and started talking to him. She mentioned she had two kids and was looking for a man who wanted more kids. He said she was beautiful. I told him months ago that exactly this kind of thing would happen if he started showing up to yoga regularly—there are so many amazing women there and not nearly enough grounded, single men. Hearing his story felt like confirmation that the kind of woman I’m looking for—someone who could become my next partner, maybe even my next wife—is already looking for me too, maybe has been for longer than I’ve realized.

Talking to him made me recognize something important: I’ll need to shift my approach. After years of being married, I’ve trained myself to keep my energy friendly but contained—to never let it cross into anything suggestive, flirty, or remotely sexual. It feels strange now to encourage my mind to move back in that direction. When I was single, that energy was automatic. I’d meet a woman and immediately ask if she was single, and often, I’d ask for her number with a clear dating intention.

I don’t want to swing that far back, but I do want to consciously reawaken that side of myself. This time, I want connection first, flirtation second. I want to really see a girl before deciding to pursue her. But I’m grateful that I have the awareness to know this is a transition—to recognize that the way I relate to women is something I’ll need to relearn, and that I’m ready to do it with intention.

There were so many times I saw girls at my yoga studio who were breathtakingly beautiful—open, friendly, smiling at me—and if I’d been single, I would’ve made sure to talk to them. But being married changed that. I’d look at a woman and think, She’s gorgeous, but there’s no reason to go there. Don’t start something you can’t finish. Even so, I still found myself developing a few crushes and forming some genuine friendships there. Now that I’m single again, I feel a real excitement about what comes next in my dating life. There’s this new curiosity, this sense of possibility.

Before my ex-wife got home with the kids, I went to my 4 p.m. AA meeting. We had a solid discussion—two newcomers and three of us regulars. It was a great mix, and the conversation flowed easily. Afterward, I came home, tidied up around the house, and played Uno No Mercy with the kids before bedtime. Once they were asleep, I spent about half an hour talking to my mom, mostly listening as she shared what was going on in her life.

Later, my ex-wife and I had another good talk before bed. It amazes me how much tension used to fill that time of night between us. Bedtime was often the only window in the day when we might have sex, and that created pressure on both sides. Sometimes it went beautifully—she’d be playful and we’d have fun—but other nights it felt heavy, like something we had to get through instead of something we both wanted. It’s astonishing how peaceful our conversations have become now that sex is no longer hanging in the air.

At the same time, I feel this new wave of excitement knowing there are probably a hundred women in St. Petersburg who I’d be deeply compatible with—women who would actually want to have sex with me before bed, and often. I imagine finding a partner who matches my energy and wants an active, connected life together.

I also recognize that I’m not everyone’s type. Being a man who doesn’t drink, doesn’t play video games, doesn’t watch TV, isn’t into concerts or bars, and doesn’t listen to music—well, that immediately filters out a huge portion of the dating pool. But it also filters in the women who will appreciate that. I know there are women who’ll light up when I say I’d love to go to a yoga class at my yoga studio, play tennis, explore the Dalí Museum downtown, sit together in a park, cook dinner, read books, play board games, or enjoy an active, intimate life together. Somewhere out there, there are women who’ll find that lifestyle perfect.

I’ve accepted that I’m not right for anyone who craves drama. I’m too grounded now for that. I’m not a fixer-upper anymore like I was when my ex-wife and I first met. Back then, she had to stabilize me. Today, I’ve got my life together, and that can be intimidating or unappealing to some women. I see it all the time—women dating men who clearly don’t have it together. They must be drawn to the chaos, because if they didn’t want to deal with it, they wouldn’t.

What gives me pause is the possibility that I might flip the dynamic—that I could become the “fixer” in my next relationship. I don’t want to date a woman who’s lost in addiction or dysfunction and try to rescue her. I’d much rather meet someone who already has her own life in order, so we can build something peaceful, playful, and fulfilling together—with no drama, no codependency, just joy.

I let my ex-wife go at 10:15 so she could get to bed early—she wakes up at 5:30 a.m.—and then I dove back into I Was Famous on the Internet for another hour before finally calling it a night at 11:15.

If you connect with how I live and think, you can follow the rest of my days on YouTube in my Dating playlist.

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