Love Means Knowing When to Let Go

Love Means Knowing When to Let Go

This is my journal entry from October 15, 2025, part of my daily autobiography Sober Through Separation — my real, unedited days, published in order.

my ex-wife is leaving for her work trip for the next two days, which means I’ll be staying at her house tonight and tomorrow night with the kids. I’ll also be taking them to school and picking them up today. After tennis this morning, my ex-wife and I are planning to stop by the UPS Store to get our divorce papers notarized. There’s a quiet sadness humming underneath everything, a background ache that comes and goes, but I’m trying to just move through the day as normally as possible.

After dropping the kids off at school, I head straight to the courts to play tennis with my friend. I’m overflowing with energy—almost too much of it. I pull my shirt off right away, but my game completely collapses. Every shot feels off. When I try to hit harder, the ball sails out. When I ease up, it dribbles into the net. I can’t seem to find any rhythm, and the frustration builds fast. It’s been a long time since I’ve felt this angry and powerless about something so small. My friend wins the first set 6–0 while I’m spiraling, and I can’t stop wondering what’s wrong with me.

Somewhere in the middle of the chaos, it dawns on me that it might not be about tennis at all. Maybe I’m just carrying too much emotion underneath the surface. My ex-wife and I were supposed to go on this trip together. It was one of our little “silly trips”—a few days just for the two of us to reconnect. When we first started planning the divorce, one of the earliest things we agreed on was that she should take this trip alone. We didn’t want to send mixed signals or end up stuck in a romantic setting that would only make things harder. This trip was meant to be a clean break, a symbolic shift. Now, here I am, hitting balls wildly across the court while she’s packing her bags.

We’re also planning to officially notarize the divorce papers today, which adds another layer of finality. I tell my friend a bit about what’s going on, and he listens quietly while continuing to wipe the floor with me. He wins the next set 6–1. I manage to play a few better games, but the anger and tension keep boiling up. My first serves won’t land. The few times they do, I crush them into perfect aces, which feels incredible—but they’re rare flashes. Mostly I’m flailing. My friend asks if I want to keep playing since we’ve only been out for about an hour and he’s already won the match. I tell him yes. I need to burn this energy off.

In the third set, things finally start to click. The anger begins to dissolve into focus. I win three of the next seven games before my friend calls it a day and heads off for breakfast. I thank him for sticking with me on a morning when my emotions were so out of control. He laughs and says he realized he was missing shots earlier because he wasn’t actually watching the ball. That hits me—because I realize I’ve been doing the same thing. Instead of watching the ball meet the strings, I’ve been thinking about where I want it to go next. That tiny lack of presence has been ruining my shots.

I start forcing myself to really watch the ball hit the racket. Every microsecond of that connection counts. When I do, my shots land cleaner and more precise. It’s amazing how such a simple thing—something so basic and obvious—can make such a difference. All that rage and frustration over something that, at its core, came down to not paying attention to the most important moment: contact.

It’s funny how often life is like that. We lose sight of what’s right in front of us because we’re already living in the next step.

After tennis, I call my ex-wife and meet her at the UPS Store. My emotions are all over the place. The anger I vented on the court has dissolved into sadness and grief. When I see her waiting outside, everything feels heavy but calm. We walk in together to get the divorce papers notarized, and for a moment I think about how this might look to others—two people cheerfully ending their marriage in a UPS Store. But I don’t feel embarrassed at all. When we went to get our marriage license years ago, I felt proud, and strangely enough, I feel proud again now. There’s something honorable about how we’ve handled this—how we can still show up together in good spirits, even for something as bittersweet as this.

After the papers are notarized, we walk back out to the parking lot. I can’t hold it in anymore and start crying. My ex-wife hugs me tightly, and we stand there for a moment, just letting the emotions move through. She tells me it’s been an emotional morning for her too, but that being emotional doesn’t mean it’s wrong. We both know that while it might feel easier in the short term to keep doing what we’ve been doing, this step is what’s truly best for both of us in the long run. I’m grateful I can face this pain now in exchange for a better future. That’s the kind of decision I’ve been learning to make consistently—choosing discomfort today to build something healthier tomorrow.

I drive home afterward and get ready for the noon yoga class. I take a quick shower, eat a bit of hummus, and head out. During class, my mind keeps circling around what’s next—how to expand my horizons, especially when it comes to dating and managing my finances. Last night, I even thought about writing a letter asking for help with both. As I move through the poses, I keep thinking about what that letter might say, what it would mean to actually ask for that kind of support.

The class is with one of my favorite instructors. I haven’t been to one of her classes in a while because of my schedule, so it feels good to be back. I also notice a guy I know from yoga—someone who did some handyman work at my ex-wife’s house earlier this year. He’s a good-looking guy, tall, fit, works with his hands. The kind of man I imagine women would naturally be drawn to. I remember once mentioning that to my ex-wife, and she told me she didn’t find him that attractive, which surprised me. I thought, If I were gay, he’s the kind of guy I’d probably go for. But my ex-wife’s always been drawn to different qualities in men.

I set my mat next to his, and after class, we talk for a while. I tell him about my dating situation, and he suggests using Facebook to find local events—things like meetups or community gatherings where I might naturally meet women. He tells me I should get out more, try different activities, and meet girls in their natural environment.

I tell him I’m open to trying new things but that going to an event purely for the purpose of meeting women doesn’t feel right to me. For example, I wouldn’t want to sign up for a paddleboarding class just to flirt with someone there if I’m not genuinely interested in paddleboarding. That approach feels forced and a little desperate. I already spend plenty of time in spaces with lots of women—yoga, tennis, social groups—and I enjoy those for their own sake. I think my better strategy is to deepen my existing network and let connections grow naturally through the people I already know.

The guy doesn’t seem to like that answer. He gets noticeably frustrated and tells me I’m being closed-minded and unwilling to take advice. He says if I won’t consider what he’s suggesting, he doesn’t know what else to tell me. I’m surprised by his reaction. It strikes me that he might be feeling some frustration with his own dating life, which makes him more sensitive when his advice isn’t received the way he hopes. I recognize that feeling—I’ve been there too. Just the other day, I got annoyed when a woman at yoga brushed off my suggestion about her sniffling and breathing.

Still, I take his feedback seriously. I’m open to trying new activities—as long as they’re things I’d genuinely enjoy doing for their own sake. That feels like the right balance between staying open and staying authentic.

After class, I talk with the instructor, and I can tell right away that she’s genuinely interested in our conversation. We’re catching up when a couple of people come in to tour the studio, interrupting us. I remember something from The Game about how a man who values his time doesn’t just stand around aimlessly waiting, so I take that as my cue to leave. It makes sense for the instructor to focus on the visitors anyway.

As I’m walking out, I notice her finish up with them. She catches my eye and signals that she still wants to talk, so I walk back over. I tell her about my idea for the letter—how I want to write one asking for help with dating and money, especially now that the divorce is moving forward. She listens carefully and offers a suggestion that immediately strikes me as brilliant: instead of handing people the letter by itself, she says I should include it inside one of my books and tell readers to start with it. She points out that if I just give the letter alone, most people will probably toss it into the recycling bin without reading it, but if it’s tucked inside a book, they’ll be much more likely to take it seriously—and maybe read both.

The instructor also tells me she wants a copy of Author in St. Petersburg, which she’s seen other people at my yoga studio reading. I go out to my car and grab a copy for her. I thank her for supporting my work and for giving me such practical advice. I tell her I really appreciate her listening, but I wish I’d had the chance to hear more about her. She shares a few brief updates about her life, but I tell her I’d love to talk again sometime and really catch up.

After leaving the studio, I head home and make a big salad for lunch. I know I won’t have another chance to eat until around 6:30 p.m., so I make sure it’s filling—probably a little too filling. I sit down to eat and finish listening to The Game by Neil Strauss, which I’ve been working through.

When I’m done, I look Strauss up online and see that the woman he ended the book dating—the one he seemed so happy about—broke up with him after about a year. Later, he married someone else, had a child at forty-six, and they divorced soon after. I feel grateful for what I’ve learned from his book, but I can also see how much of it doesn’t fit who I am. I have no desire to paint my nails or go “peacocking,” dressing outrageously just to grab attention. That kind of showmanship doesn’t feel authentic to me.

What does feel authentic is handing out letters inside my books. It’s my own version of standing out—unique but honest, an extension of who I really am. You could call that a kind of peacocking, I suppose, but it aligns with my identity rather than performing a role. What I take most from Strauss’s book is the reminder that it’s on me, especially as a man, to take initiative—to put myself out there, make the approach, and express what I want clearly. Waiting around for the perfect woman to show up isn’t an option. Taking action is.

On the drive to pick up the kids from school, I call my sponsor. He tells me I’m a man of action—he’s impressed that only a week after moving out, I’m already making so many moves. He asks if maybe I should take more time for myself, which is something I’ve heard from several people lately. I tell him no. I was single for most of the decade between 2000 and 2011, except for a one-year relationship I had in college before meeting my ex-wife. I’ve spent enough of my life alone to know exactly what I want now.

What’s different this time is that I’m approaching things with patience and intention. I’m not needy, but I’m also not sitting idle. It’s up to me to start planting seeds now—to take action that sets me up for the next amazing relationship when it’s time. It doesn’t make sense to me to spend months wallowing or “taking time to grieve” in the traditional way. I’ve been doing personal growth work for over a decade now through Alcoholics Anonymous, constantly reflecting, healing, and refining myself. Maybe some people, like my ex-wife, need space to process everything after a divorce—and that’s completely valid. But for me, I’ve already done that work for years. I’ve known the marriage wasn’t fulfilling me in key areas for a long time, and I’ve had clarity about that for at least a year. It just took time to translate that awareness into decisive action.

That’s why I think it would actually be insane for me to go more slowly now. One reason I seem to be doing so well through this divorce is that I’m turning my emotions into motion. If I just sat around doing nothing, I’d end up wallowing. I know how easy it would be to get lost in despair—feeling sorry for myself, imagining that I’ll never have a woman again, or numbing out with distractions like video games or porn. I don’t want that life. When I feel sadness, like I did this morning, it fuels me. If I’m sad about the divorce, I take that energy and ask, “What can I do right now to move forward?”

So I channel those emotions into action—writing and editing my books, drafting this letter I want to include with them, asking people for feedback and advice, and continuing to build my next chapter. Either I take conscious control of my energy and aim it toward what I want, or I drift into unconscious habits that keep me stuck.

When I pick up the kids, the car feels stiflingly hot, so I shut the air conditioning off while we wait in the school line. We make a quick stop at my house to grab seaweed snacks before heading to my ex-wife’s so they can have a little bite to eat. My ex-wife’s mom comes by to pick them up, since I’ve arranged for her to drop them off with my mom afterward. That way, I can attend two AA meetings back-to-back—I don’t want to miss tonight’s speaker.

It’s the first time I’ve seen my ex-wife’s mom since the divorce plans became public a few weeks ago. She greets me warmly, gives me a hug, and tells me she’s grateful for how my ex-wife and I are handling everything. She’s supportive of both of us and proud of how we’re navigating this transition. I tell her I appreciate her being there for my ex-wife and encouraging her to move forward, and I thank her for her kindness toward me as well.

That interaction reassures me that this path is truly the right one. If this weren’t the right decision, I don’t think there would be this much grace, support, and mutual gratitude among all of us. My ex-wife’s mom’s warmth feels like a confirmation that we’re doing exactly what we need to for everyone’s happiness.

After my ex-wife’s mom takes the kids to her house, I start up my Toyota Corolla—and immediately sense something’s wrong. The engine is shaking visibly under the hood, rumbling unevenly like it might stall out at any second. I pop the hood and take a look, though I’m not a mechanic. Still, I can tell something’s off with the cooling system. When I get back in, I notice the temperature gauge climbing—almost touching the red zone for overheating.

My dad’s voice comes to mind instantly: If your car starts overheating, turn the heat on full blast to vent the engine. I crank the temperature all the way up, switch the fan to maximum, and roll down all the windows. It’s instinct now—stay calm, follow the steps. I get this strong intuitive nudge that I should take the car straight to the dealership. Whatever’s happening, it needs to be dealt with now, especially since I’ve got childcare covered and the service department will be closing soon.

I call the woman who started the AA meeting with me to confirm she’ll be there to open up. She says yes, so I head straight to the Toyota dealership, windows down and heat blasting. Thankfully, it’s only in the low 80s outside, which makes the ride tolerable as the hot air rushes out. After driving a few blocks, I see the temperature gauge drop back to normal, and I feel relieved. I make it to AutoNation without an appointment a little after 4:00 p.m.

While I’m there, the girl from AA texts me again—she’s been held up at school and will be fifteen minutes late. I sigh and hope the meeting goes smoothly without us. A guy who was there yesterday calls to ask whether they should start without me. I tell him the girl might arrive soon, but they can go ahead. He says there are five people there already, and I’m glad they managed to get into the room even without either of us unlocking it.

Inside the dealership, the service advisor tells me the diagnostic fee is $200, but they’ll waive it if I approve the repair once they find the issue. I agree. He suspects it’s the radiator fan, which makes perfect sense—the air conditioning works great while I’m driving, but when the car idles, it starts to overheat. I hope it’s a straightforward and affordable fix. The last time I came here, the bill was $4,000, and I don’t want to go through that again.

I head over to the rental car desk to get a loaner, as usual. But the process has changed since the last time I was here. Now they’ve added a new checkbox requiring renters to confirm they have collision insurance. It makes sense, given that they’re handing out cars worth $20,000 to $40,000.

That’s when I realize I’m in a bind. My policy doesn’t include collision anymore—I dropped it a couple of months ago because it’s not legally required. I’d gotten tired of paying hundreds of dollars a month for coverage I never used. I haven’t had any accidents with other cars, just the one time I drunkenly wrecked my own car into a curb years ago and drove it home without ever reporting it.

As I stare at the form, I realize I could just check the box and lie. Nobody else would ever know. But that thought immediately clashes with my values. I’ve spent too many years in recovery and self-reflection to start compromising my integrity over something this small. So I tell the truth. I explain that I only carry the state-required minimum—$10,000 in personal injury protection and $10,000 in property damage liability. Dropping all the extras saved me nearly $200 a month, and since my ex-wife’s still on the same policy, that’s about $100 of savings just for my share.

The rental desk attendant double-checks with her manager, but the answer is final: no collision insurance, no rental. I ask if they can at least give me a shuttle to the Enterprise down the road, and they agree. The driver drops me off a mile away, and I walk inside hoping for better luck.

The girl at the Enterprise counter looks up from her screen and tells me flatly that without a reservation, they don’t have any cars available. I take a breath and smile, reminding myself—just another test of patience. “Okay,” I say. “That’s fine.”

I walk out of Enterprise and pull up the Uber app on my phone. It’s been a while since I’ve used it, so I have to update my phone number and confirm my email before I can request a ride. Once I get it set up, I order an Uber to pick me up. As I wait, I notice how calm I feel. After the explosive frustration I unleashed during tennis this morning, none of these setbacks—the car breaking down, striking out twice on rentals, missing the AA meeting I started—have stirred any anger in me. I just feel acceptance. Everything’s working out however it needs to.

About ten minutes later, my driver pulls up. The ride back to the AA meeting is only about $17, and I’m grateful the meeting is close—just a ten-minute walk from the house I’m renting. I decide to have him drop me off there. The driver’s from Cuba, and we strike up a conversation about how Uber works. He explains that, depending on his expenses and income, he often doesn’t have to pay taxes if he stays below a certain threshold. I wonder if that’s because the mileage deductions balance out his earnings. It’s interesting, though it’s clear to me I’d never want to do it myself. He tells me he averages around $20 an hour, which makes sense but confirms I’d rather spend that time writing. Still, I appreciate the insight. When we arrive, I give him a $20 tip. He’s genuinely grateful, which feels good.

Right as I’m stepping out of the car, I notice a homeless woman standing outside waiting for me. I recognize her immediately—she’s the same woman I mentioned in Author in St. Petersburg. Without hesitation, I reach into my wallet and hand her a $20 bill. Her eyes light up. She tells me that God told her to come here today, that she had a feeling she’d see me. I tell her she’s definitely tuned in because I almost never come to this meeting, and the last time she saw me was at a completely different one downtown, nearly thirty blocks away and at a different time of day.

It always amazes me how some people who live on the streets seem deeply connected to something larger—a kind of collective intuition that most of us miss in our daily busyness. Here’s a woman who’s battled addiction and health problems, who walks the streets with nothing, yet she feels guided by something higher and shows up exactly where she needs to be. She tells me she plans to stay for the meeting and clean up, but after she gets a cup of coffee, I don’t see her again.

I sit down and talk with the speaker before the meeting starts. I’ve known him for years, but this is the first time I’ve heard his full story. I listen for the next hour, grateful to just sit, breathe, and absorb someone else’s experience.

After the meeting, I walk home. I gather some essentials for the night—clothes, my laptop—and clean up around the house, throwing laundry in the dryer and tidying a few things before heading down the street to my ex-wife’s. From there, I walk over to my mom’s place, where she’s spending the evening with the kids. They’re laughing and happy to see me. I take out the trash and grab a couple of her old dog beds the kids want to bring to one of the rescues.

My daughter and I share an ice cream sandwich—just half for me. I’ve realized I enjoy the first half the most; after that, it’s just extra sugar I don’t need. We head back across the street, and I start feeling a little irritated and restless. I’m missing my ex-wife, and it feels strange doing bedtime in her house again now that I’ve moved out. I haven’t done bedtime solo in over a year.

Then I remind myself—there’s no reason to make it harder than it needs to be. I already know what works. I tell the kids that if they’re in bed by 8:25, they’ll each get $5. Immediately, they spring into action. My daughter hops in the shower, my son follows, and my attitude shifts right along with theirs.

As I take the trash out again, I shake my head at how simple it really is. We already have strategies that work beautifully in our lives, yet we forget to use them and choose unnecessary struggle instead. It’s such a human thing—to resist what’s easy, even when we already know the way.

I get the kids tucked into bed and say goodnight, singing You Are My Sunshine like I’ve done so many times before. My ex-wife has left a handwritten note on their bed with the song’s lyrics, written in her beautiful cursive with colored pencils in shades of blue, yellow, pink, and green. It’s such a tender touch—one that makes the whole room feel alive with her spirit.

I lie down next to my son for a little while, wrapping my arms around him as he drifts off. As he settles in, I start to cry quietly. I miss my ex-wife and the life we built together—the comfort, the rhythm, the sense of home that came with being a family under one roof. But even as the tears fall, I feel gratitude. Missing her doesn’t mean we should get back together. Love doesn’t always mean staying married. Sometimes love means knowing when to let go and allowing each other to grow in separate directions.

Earlier in the day, after I’d gotten home from the AA meeting, my ex-wife and I talked on the phone. She said she’d been feeling some sadness too and had spent part of the day missing me. Still, she was enjoying the freedom of her solo trip to Fort Lauderdale. She laughed as she told me she stopped at McDonald’s on the drive—something I would’ve hated doing—and how much she liked that she could do it on her own terms. Her order number was 666. At first, she was unnerved, but she looked it up as an angel number instead of a devil’s sign, and it turned out to be about finding balance—exactly what she’s working on in her life. We both laughed about that. She said even the woman at the counter looked uncomfortable and apologized for the number.

My ex-wife mentioned that she went to a hot workout class at her hotel wearing just her leggings and sports bra—the kind of thing I’d encouraged her to do for years. A part of me felt sad hearing that. It’s strange that she’s now doing some of the very things I used to suggest only after we separated. But at the same time, I’m happy for her. It’s important that she explore what she actually wants, not what I thought would make her happy. For years, I tried to mirror back to her the desires I saw inside her, but I think she often took that as me trying to control her. Now she’s discovering those things on her own, and I’m genuinely glad for that, even if it took our divorce to spark the change.

She said she’s been enjoying ordering room service, though she felt a little pang of sadness when she saw the restaurant downstairs serving Impossible Burgers—something we would have shared if we were there together. Even so, both of us can sense that where we are now is exactly where we need to be.

We also talked about my letter-writing idea. My ex-wife said she thinks it’s perfect for who I am—an honest, heartfelt way to reach people and deepen my connection with readers. She loves the concept of tucking the letter inside my books. Her advice was to keep it concise, maybe even use bullet points instead of my usual long, winding letters. I smiled at that because she’s right—I do tend to write too much sometimes. But I also know that’s part of who I am: someone who feels things deeply and wants to share them completely.

Even as I lay there next to my son, missing my ex-wife, I can feel that everything is unfolding exactly as it should.

I keep all this in mind as I sit in the kids’ room while they’re falling asleep. The house is quiet except for the soft sound of their breathing. I sit down at my daughter’s little desk, open my laptop, and start working on the letter. Earlier, while I was at my own house, I took about thirty minutes to dictate the raw material for it. I’d run the transcript through MacWhisper, then dropped the whole thing into ChatGPT with instructions to help me turn it into a clean, structured letter using bullet points.

I go back and forth with ChatGPT for over an hour, refining and shaping it. Having its help with the structure is such a relief—it’s the kind of thing that would’ve taken me hours to do alone. It takes my raw dictation and organizes it into a polished format with ease. By the end of about an hour and a half, I have a finished two-page letter, single-spaced, narrow margins, twelve-point font. It fits perfectly on one double-sided sheet, exactly what I’d envisioned—something I can print and slip into the front of one of my books.

I feel great about the length and the design. More than half of it is formatted with bullet points and concise sentences that make it easy to read. The letter starts by explaining why I’m writing it—what I’m seeking and why I’m reaching out. The first section, on money, was the instructor’s suggestion; she told me to start there before moving into dating. The next section focuses on relationships, and together they paint a clear, honest picture of who I am and what I’m looking for.

The letter openly invites advice, feedback, and connection. I make it clear that I don’t have all the answers—that I’m figuring things out and that I’m genuinely interested in the reader’s thoughts, ideas, or help. That’s what I love about this letter: it creates an authentic bridge between me and whoever receives it. I could slip it inside a book and hand it to the kind of woman I’d love to meet, someone who might begin to fall for me as she reads my words. Or maybe I’d give it to her parents, and they’d read it and think, This is exactly the kind of man our daughter should meet. They might pass it along to her. Or it could happen through a friend—maybe I give it to a guy who realizes one of his ex-girlfriends is exactly who I’m describing, and he shares it with her.

It feels powerful to think about how many possibilities exist through the people I already know. I personally know hundreds of people, and each of them knows thousands more. Just by putting this letter into circulation, I could be opening doors far beyond my immediate reach. Reading it out loud, I can hear how authentically it expresses what I want and what I offer.

ChatGPT helps me smooth the tone in places that were too blunt. In my first version, I’d written lines like, I’ve never been arrested, never been sued, never had an STD, and I want a woman who’s not obsessed with her career and wants to stay home with the kids. Those points were true but came across as harsh and clinical. It softened them into something more inviting and romantic. I also asked it to rewrite the section about wanting daily sex, since my original phrasing was a bit too direct. It reframed it beautifully, turning it into a bullet point about physical touch as my love language and loving daily connection and lovemaking as part of a joyful relationship. It conveys exactly what I meant—clear and honest, but warm and human.

By the time I finish, I feel deeply satisfied. The letter says everything I want it to, in my voice, but refined and approachable. I close my laptop, take a shower, and get in bed right at 11:11 p.m.—a time that feels like a little wink from the universe, confirming that I’m on the right path.

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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