Man, love. That whole thing, right? For the longest time, I thought it was like some kind of complicated engine. You had all these parts, and if you just put them together in the right order, turned the right screws, it’d hum along perfectly. I used to spend so much time trying to figure out the “rules.”
I was always the guy who’d overthink everything. A date? Oh, I’d plan it down to the minute. What we’d talk about, what jokes I’d tell, even contingency plans if it rained. I’d try to anticipate every single thing. Thought if I just had enough data, enough “logic,” I could guarantee a good outcome. I mean, that’s how you ace a project at work, right? Just meticulous planning and execution.
Turns out, people aren’t projects. Who knew? I went through a bunch of relationships in my twenties, and they all kind of… sputtered out. Each time, I’d go back and analyze, try to find the “bug” in my system. Was my humor off? Did I not listen enough? Did I listen too much? It was exhausting, man. And frankly, it just made me feel like I was constantly failing, like there was some secret manual everyone else got but me.
The turning point, though, was this one relationship, probably my most serious one at the time. It was good, or I thought it was. We had plans, we talked about the future, all that jazz. But underneath it all, I was still doing my thing: over-analyzing, nitpicking little things I thought were “flaws,” trying to subtly steer everything towards what I considered “ideal.” I wasn’t really engaging; I was managing. And then, boom. She just… left. Just like that. Said she couldn’t take it anymore. Said she felt like she was constantly being evaluated, not loved.
That hit me like a ton of bricks. Really knocked the wind out of me. I spent weeks just staring at the ceiling, playing it all back. Every single interaction, every argument, every quiet moment. My “perfect plan” had completely blown up in my face. I was so convinced I was doing everything “right” by my own messed-up logic, but I was actually just making her miserable, and me too, without even realizing it. I was so caught up in the details, I missed the whole damn point of being with someone.
What I started doing different, from the ground up
After that, I knew I had to fundamentally change how I approached things. This wasn’t just a tweak; it was a total overhaul of my operating system. I didn’t immediately jump back into dating. I couldn’t. I had to figure out what went wrong with me first. So, I started by just… observing. I watched couples who seemed happy. Not the super lovey-dovey ones, but the ones who just had that quiet, comfortable vibe. And I listened, really listened, to friends talk about their relationships, good and bad.
My first big “practice” step was learning to shut my mouth and just listen. Sounds simple, right? It wasn’t for me. My brain constantly wanted to jump in, offer advice, correct a minor factual error, or plan my next sentence. I forced myself to just absorb what the other person was saying. No immediate judgment, no formulating a response. Just take it in. I started doing this with everyone, not just potential dates. Friends, family, even the barista. It was uncomfortable at first, like flexing a muscle I never used. But man, people open up when they feel truly heard.
Then, I started ditching the “perfect plan” mentality. Dates became less about hitting a sequence of pre-approved events and more about just doing something simple and seeing where it went. Coffee, a walk, something casual. The goal wasn’t to “impress”; it was to simply connect. To actually talk to someone, not at them. I had to learn to be present, instead of always thinking three steps ahead.
I also realized I was a really bad apologizer. When I screwed up, I’d always try to explain why I did what I did, hoping that explanation would somehow lessen the impact of my mistake. But that’s not an apology, is it? It’s an excuse. So, I practiced just saying, “I messed up. I’m sorry.” No buts, no excuses. Just owning it. And then, I’d try to actually do something different next time, instead of just saying I would.
Here are some of the simple “tips” I stumbled upon, not from a book, but from actually living through the mess:
- Authenticity beats perfection, every single time. Trying to be someone you’re not, or trying to achieve some movie-perfect ideal, is just a recipe for disaster. Be real. Flaws and all. People connect with that way more than some polished facade.
- Listen to understand, not to reply. This was massive for me. Seriously, stop planning your comeback. Just soak in what they’re saying. You’ll catch so much more, and people will feel genuinely valued.
- Small, consistent gestures are gold. Forget the grand, one-off romantic gestures. A text asking how their day is going, remembering a small detail they mentioned, a quick “thinking of you” – that stuff builds real connection over time. It shows you’re paying attention and you care, day in and day out.
- Learn to pick your battles. Not everything needs to be “correct.” Sometimes, just letting something go, or agreeing to disagree on a trivial point, saves a lot of heartache. Figure out what truly matters and hold firm there, but let the little stuff slide.
- You gotta take care of your own garden first. No one else can fill a void in you. If you’re not happy with yourself, if you’re not doing things that make you feel good, you’re bringing a whole lot of baggage into any relationship. Figure yourself out first.
It’s still not perfect, man. No relationship ever is. But my whole approach changed. I stopped trying to engineer love and started trying to experience it. I actually started dating again, after a long break. And this time, it felt different. It felt… lighter. More honest. Less like a project, more like an adventure. And yeah, I eventually found someone who appreciates the real me, even with all my quirks. Because I finally learned to let her see him.
