My Most Embarrassing Moment on the Tennis Court

My Most Embarrassing Moment on the Tennis Court

This is my journal entry from October 14, 2025, part of my daily autobiography Sober Through Separation — my real, unedited days, published in order.

I couldn’t stop laughing for half an hour tonight over something I said—“I wish I could come.” The phrase itself isn’t funny until you know the context. I’ve been listening to The Game by Neil Strauss, which is wild because I used to watch a ton of Owen Cook’s old “free tour” videos on YouTube without realizing he’s actually RSD Tyler—Tyler Durden—the same guy from Strauss’s pickup artist circle. It’s strange how these worlds overlap. Different mediums, same ideas, just resurfacing years later in my life when I’m suddenly open to them again.

Lately, I’ve been thinking about working on my pickup game. I want to practice approaching women again—be more fun, confident, cocky, playful. I’ve been too serious for too long. It makes sense though; after being married for over a decade, I conditioned myself to be boring and lukewarm at best, partly out of fear that if I showed too much energy or charm, I’d be “asking for trouble.” But now, everything’s flipped. Suddenly I want the opposite—to walk up to the hottest woman in the room, talk to her, and see what happens. Maybe even see how crazy she is.

Tonight, I met my friend for a men’s singles ladder match at the tennis club. Our court was right next to one of the women’s tennis clinics, which I saw as the perfect chance to try “peacocking”—the art of getting attention, like a male peacock showing off its feathers. I got to the club early, around 5:40 p.m. for our 6:00 match. My friend showed up early too, and we started warming up. I won the first set 6–2, and we moved to another court for the second since I could only reserve the first one for an hour. The new court was ideal because it still had visibility to the women’s clinic.

The most attractive woman there—probably out of fifteen or twenty—was pushing her bike across the courts near us. My mind immediately kicked into The Game mode. This was my moment to practice. I looked at her and said something like, “Did you have fun playing over there?” She said she did, and I—without thinking—replied, “I wish I could come.”

The second it left my mouth, I died inside. I could barely hold it together. I meant “I wish I could come to the women’s clinic,” but of course, it sounded exactly like what it sounded like. My brain instantly roasted me: I bet you do, bro. I bet you do.

I couldn’t stop laughing. I lost at least two games because I was so thrown off. It was one of those moments so embarrassing it became hilarious. I hadn’t talked to a woman like that in so long that my rust showed instantly. I’d been waiting for a perfect setup, and the first thing out of my mouth turned into sexual innuendo. Classic.

When the women started another clinic and were in full view of our court, I made things even worse by missing several easy shots in a row. I started overcompensating—jumping around, exaggerating my follow-throughs, acting like I was performing for an audience. At this point, I wasn’t even pretending to play seriously; I was pure theater.

The coach on the court next to us joked that he wished he was still eighteen, and I thought, Man, I feel eighteen right now. Peacocking on the court, saying dumb shit to women, and loving every awkward second of it. Despite the disaster, it felt good to be in the game again—to be out there, taking risks, laughing at myself instead of hiding behind caution or fear.

Later, I saw that same woman had a picture on her phone with a good-looking guy who, judging by his expression, definitely wasn’t her brother. She probably has a boyfriend. That’s fine—my job is to approach, not to expect results. Funny enough, she left her phone sitting on top of my tennis bag at one point. I noticed it and laughed to myself: That’s about as close as I’m getting tonight. Still, I’ll take it.

My friend eked out the second set 7–5, but by the end his legs were cramping badly. I told him about how my friend had to forfeit against me once because he got too tired halfway through the second set to finish me off. My friend was determined not to suffer the same fate. Still, the cramps kept getting worse, so he started swinging for winners on every shot—and somehow, it worked. He stopped trying to rally and began crushing balls down the lines and corners. Ironically, by refusing to move much, he actually started playing better and whooping on me.

We’d had an epic game earlier that went to more than ten deuces, and that’s when his legs really began to seize up. I was proud I even got the second set as close as I did, especially considering I’d been down 5–2 after laughing so hard about “I wish I could come.”

The third set was competitive. I started bombing serves—some so fast that my friend didn’t even swing. I’d love to know how fast they were clocking in, because it felt like I was finally serving at the level I used to dream about. When I first started playing tennis, I used to watch people hit aces and think, Man, that’s when you know you’ve made it. Now I was hitting serves that exploded off the line and left him frozen.

Last year, my friend had a monster serve too, but it went out so often he switched to a safer spin serve. I told him I missed that old cannon of his. To me, the sexiest serve in tennis is the one you blast disgustingly hard and watch rocket past your opponent before they can even react. One of mine hit the line and bounced off unpredictably—he laughed and even complimented my serve afterward, which felt good.

He managed to squeak out the win in the third set, 6–4. Later, he texted me saying he was still cramping up. I had no idea how to reply—what do you even say to that? I just felt good that we’d pushed each other that hard.

I made it home right around 8:30 p.m., just in time to say goodnight to the kids—five minutes after my ex-wife had put them to bed and turned the lights out. She’d been watching me on the phone, tracking the match, so she knew when I’d be done.

Earlier that evening, before we left the courts, I overheard one of the women in the clinic shout, “Scheisse,” which is German for “shit.” I couldn’t help saying, “Oh, you’re speaking German out here!” She laughed and said she picked it up from the coach. I joked back in German that I spoke a little too, but nobody else said anything. That’s when it hit me again—I know what I need to do. I need to keep peacocking. It doesn’t matter how often it doesn’t “work.” What matters is how much fun I’m having.

Peacocking feels natural to me—playful, bold, expressive. I’ve been doing it my whole life, long before I knew the word for it. It’s what made me famous online in the first place. I’d throw on a women’s tube top, act ridiculous, and get thousands of dudes clicking on my stream wondering what the hell was going on. That’s the essence of peacocking—making people look, laugh, and feel something. And that’s exactly the energy I’m bringing back into my real life.

When I got back to my apartment, I put The Game back on. Neil Strauss was describing his wild pickup-artist exploits, and I looked around my little bachelor pad feeling like my life kind of sucked in comparison. But that’s okay. I’m learning. I’m growing. And honestly, I’m not trying to be one of these fuckboys anyway.

I thought about Owen Cook—RSD Tyler, Tyler Durden—the same guy from those old pickup videos I used to watch. He’s charismatic, sure, but the man’s got kids with multiple women and doesn’t seem to have any kind of steady, loving relationship. That’s not what I want. I don’t want to be the guy approaching women for the rest of his life… although part of me wonders if maybe I do.

Lying in bed that night, I realized I didn’t even know what I wanted anymore, or who to think about—though at least I wasn’t scrolling through dating profiles again. My mind drifted to a massage therapist I know, even though she still hadn’t messaged me back since Friday. She’s in Sarasota, and it probably makes sense for both of us to look closer to home.

Afterward, I showered and got back to work editing my diary transcripts through ChatGPT. I’d hit 32,000 words so far, and at this pace, I should have the next diary book finished within a few days.

Out of curiosity, I made the mistake of checking my Amazon sales for the first time since publishing. I’ve spent hundreds of dollars printing books and giving them away, and I’ve made maybe twenty bucks in online sales. Still, I’m glad I checked. Amazon doesn’t shove analytics in your face like YouTube does. The books will be there indefinitely—books I can look back on years from now to see exactly where I was in life. Books my kids can read someday. Books that might even inspire someone to work with me.

While I was showering, I had another idea. I realized I need to tell women something different when they ask what I do. The other day at yoga, I told a girl I was a writer, and I could feel her interest drop instantly. A writer? It sounded like code for broke dreamer. I need something better. Next time a woman asks what I do, I’m going to say, “I charge people hundreds of dollars an hour to talk to me—so I hope you’re enjoying the free chat.” It’s cocky, confident, and funny.

Of course, if I’m going to say that, I actually need to charge that much. Right now, I offer two-hour sessions for $333, and my AA-style meeting is called “444.” So it feels natural to bump the price up to $444.44 for two hours with me. If someone’s willing to pay $333, they can pay $444. A hundred bucks difference means nothing to someone already spending that kind of money.

And who knows—if these books ever really start circulating, people might come from out of town just to meet me. Someone might book a flight, get a hotel, and spend an entire week doing daily sessions. That’s what Neil Strauss described in The Game—how he paid $500 to attend a workshop with Mystery. I could be that kind of person for others: someone people travel to see, just to talk, learn, and grow.

I don’t really like the idea of running workshops anymore. They sound great in theory, but the logistics kill it—building lists, organizing groups, teaching on a fixed schedule. That’s not the life I want. I’d rather just be the guy people pay $400 for a couple of hours to hang out, talk, or play board games with. That feels natural to me—personal, spontaneous, fun. And honestly, that would make rent easy. Five of those sessions a week would be over $2,000, more than $8,000 a month, plus whatever royalties eventually come in from my books. That’s a lifestyle I can actually see myself enjoying.

I started tonight’s diary with the tennis story because it was too funny not to, but now I’ll rewind to this morning. The kids had school, though it felt like a Monday since they’d had the previous day off. After dropping them off, I went to a 9 a.m. yoga class with one of the best instructors. I was keeping an eye out for women I could try an approach on, but none really caught my attention. There was one next to me I thought about talking to, but she got up and left early. I laughed to myself, thinking, Well, you just saved yourself from me approaching you today.

I’ve been thinking I need some kind of routine—a playful but genuine way to go deeper with women I meet. Something that doesn’t feel forced but still opens a real connection. An idea hit me: what if I told a girl, “Hey, I want to practice my psychic readings on you. It works best on someone I don’t know at all. Want to give it a shot?” Sure, some girls would think I’m a total weirdo, but the yoga crowd is usually open-minded—at least two-thirds of them would be down to play along.

Then I could start with something like, “I think your name starts with an A sound,” and see if I get lucky with a detail. “Are you single or in a relationship?” I could make it fun, teasing them into revealing things about themselves without it feeling like a normal conversation. Ideally, they’d walk away curious about me, maybe even eager to give me their number, and then we’d go out, have sex all the time, and she’d want to have my kids and support my writing career. Perfectly reasonable, right?

After yoga, I called my mom around 10:15 a.m. to take her to MacDill Air Force Base like we’d planned, but she wasn’t ready yet. I stayed home, had some hummus, and worked on setting up my office. Everything’s finally organized—computer plugged in, workspace clean—and I submitted I Was Famous on the Internet to Kindle today. I got the email later tonight confirming it’s live.

Part of me hopes Kindle Unlimited might actually work for me. I Was Famous on the Internet feels like the kind of book that could do well there. Still, I probably need to run some ads to get initial traction. A few clicks, some steady visibility—something to get the algorithm moving. But I don’t want to throw money away on ads until I’ve got more books published. If I only have two or three, what’s the point? Once I have ten or more, though, a single ad could generate $40 or $50 in royalties. Then it starts to make sense. And who knows—maybe those ads could bring in people willing to drop $400 for an in-person session, too.

After about an hour getting everything in my office set up, my mom called to say she was finally ready to go. I walked down to her house, and we got into her silver Ford Explorer to drive over to MacDill Air Force Base. For some reason, I felt a little sad today. My ex-wife’s leaving tomorrow for a work trip—the same trip that was supposed to be our little annual getaway, our one time a year to just be together somewhere different. Now she’s going alone, and I’ll be staying home doing my usual routines: writing, yoga, and tennis. It hit me that I wasn’t sad because of her trip itself, but because this visit to the base was different. This time I was going there to shop for myself—for my house—not for our family. The realization carried a quiet grief, the kind that doesn’t scream but hums in the background. Still, I felt grateful to be spending time with my mom. There’s always a sense of nostalgia driving onto the base—the smell of the air, the military structure of the buildings, the feeling that I’m revisiting a chapter from years ago.

Earlier that morning at yoga, I’d been wondering if anyone would notice my haircut. A woman I’ve seen in class for years did, and we always say hi. She usually comes in a few minutes after class starts, which I secretly like because it makes me feel better about coming in late myself. One of the instructors always says, “Some is better than none,” encouraging people to join no matter when they can make it. She glanced at me and said, “Nice haircut—looks good on you.” I told her thanks. She’s married, and I don’t flirt with women who are taken, but I appreciated her saying it. I’d been wondering if I looked better with this cleaner style, and that quick validation felt nice.

In The Game, Neil Strauss talks about how crucial grooming is, and it made me realize how many times I’ve let my hair get long and sloppy in the past, especially with my ex-wife. It was easy to rationalize—why bother if I’m already married? But now, I’m thinking differently. If I want to peacock properly, I need to keep myself sharp. It reminds me of that Katy Perry song about wanting to see someone’s “peacock.” Exactly.

So I took my new buzz cut out to MacDill, wearing this gold eagle necklace my mom bought me there last year from one of the outdoor vendors. We walked through the Exchange, and it took me way too long to find the toothpaste aisle. Finally, just as I spotted it, a guy in uniform walked by, glanced at my necklace, and said, “Hey, I love your necklace—it looks expensive.” I smiled and told him it wasn’t, that it cost less than $100 and he could get it right outside. He looked genuinely happy to hear that, thanked me, and walked off.

I felt validated—like, damn, even a good-looking man in uniform just complimented me. Then of course my mind couldn’t resist spinning: Was that just him being nice? Or was he gay? Either way, it made me laugh to myself as we kept shopping.

I honestly couldn’t tell what kind of energy I was putting out. The compliment from the man in uniform had me thinking about attraction and how people perceive me. It also made me think of an old friend of mine — the first gay man I ever got close to, back around 2009. That friendship changed me. Back then I carried a lot of homophobia I’d absorbed from my father, and I’d never really thought for myself about it. Once he came out to me, I realized it simply didn’t matter to me — if anything, our friendship deepened, and I let go of a prejudice I’d never actually chosen.

Anyway, what a tangent — all this because a guy complimented my necklace.

After finishing up at the Exchange with my mom, we decided to grab lunch. I went to Subway while she skipped eating—she’d wanted a juice from a nearby place, but it had just closed and was being replaced by a new Mexican restaurant with some long name. I made it my mission at Subway to practice being confident, funny, and playful, even if I wasn’t trying to pick anyone up.

The woman on the far right behind the counter wasn’t having it—mask on, no smile, just grinding through her shift. But the other two women were cracking up by the time I was done ordering. One of them laughed the hardest when I asked, “Do you ever dream about Subway?” She said, “No way, I get enough of this while I’m here.” It felt good to make people laugh again, just for fun.

After we ate—well, after I ate—we headed to the commissary to shop. I loaded up the cart, going full prepper mode. I bought ten packs of six seaweed snack bags each, because they were only $4.62 per pack with no tax, compared to around $16 for sixteen of them on Amazon. That kind of math makes me feel like I’m winning at life, even if it’s just with seaweed.

The sadness really hit me in the commissary. Walking through those aisles, I couldn’t help remembering all the times I’d come here with my ex-wife and the kids—shopping as a family, laughing, filling the cart with things for our home together. Even when I’d come with my mom before, it was for all of us. This time, it was just for me. That shift hurt in a quiet, subtle way.

Still, I bought the kids their vitamins—they’re only eight dollars and some change here instead of sixteen at Whole Foods. Mom and I filled the cart to the brim, chatting with the workers and navigating the aisles together. She’s always friendly with people, the kind who can strike up an easy conversation anywhere. The total came out to just under $500, which I reminded her was actually less than what we’ve spent before.

Since she has the military ID, she’s the one who pays at the commissary. I figured if she asked for a couple hundred back, I’d give it to her, or if she went through the receipt and highlighted things, I’d send her something. But she didn’t ask, and I didn’t offer. She’s a great mom, and I know she likes helping me out, especially now that I’m going through the divorce. Besides, she spent thousands flying out for my brother’s second wedding—she won’t have to spend anything for mine, whenever that happens. If I can even find a hostage to take around here. Just kidding. What I really want is a lovely woman who sees me as the man she’s been waiting for—someone who realizes she’s been settling for shallow sex and empty relationships with men who never showed up fully.

When we got back, I split the groceries between houses—brought a bag over to my ex-wife’s for the kids, then took the rest to my place. By four o’clock, I was at my men’s AA meeting, reading a story from Experience, Strength, and Hope, the book that collects stories cut from the first three editions of the Big Book. I picked one about a guy who was a five-time convicted felon who found sobriety in prison. I didn’t know why that story stood out to me—it just did. After I finished reading, a few other men shared that they’d been to prison too, and the story really spoke to them. I sat there thinking, Damn. That’s some intuitive, psychic-level shit right there.

That kind of thing happens to me a lot—these little flashes of intuition that seem to land exactly where they need to. It’s why I want to find someone in town who can actually help me develop my psychic ability further. Not some amateur with tarot cards or generic “energy readings,” but someone who knows how to train intuition properly. Someone who can teach me to read people quickly and clearly—to strengthen the sensitivity I already have.

After the meeting, I came back to my bachelor house, got ready for tennis with my friend, and showed up twenty minutes early—rare for me. Just a couple of hours later, I’d be on that same court saying to a beautiful woman, “I wish I could come.” It still makes me laugh.

I love taking this tour through my mind and pouring it all out onto paper. Hardly anyone’s read my books yet, but I already see myself as a best-selling author. Someday, someone will find all of this—start with Author in St. Petersburg and keep reading through every diary, every page of my life—and they’ll think it’s the best thing they’ve ever read.

If that’s you, thank you. I appreciate you. I see you. Well, not literally—I’m sitting alone on my couch right now, ready for bed—but I feel you in spirit. And I hope someday we get the chance to actually talk.

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

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