The Dating Habits of Winners
What most people get wrong.
I am not a relationship expert. If anything, I am a hypocrite.
I am not a relationship expert, but I’ve written literally hundreds of articles on relationships online (that are under someone else’s name). I haven’t had a crazy amount of relationship experience, but I have had enough experience to tell you what not to do.
I’ve had more bad relationships than good ones. I’ve read a lot and studied a lot about relationships both for my work and because if I didn’t, I’d be completely lost and stuck in the same cycles of bad relationships and anxiety, over and over again.
For me to write an article titled “The Dating Habits of Winners” implies a lot of things, none of which I know to be true, but all of which I hope to be true. It implies that I’m a winner and that I’m having a winning relationship. It implies that I’m winning the relationship game.
Right now, for once, I am doing very well. I’m in a great, loving relationship. I have a partner whom I love deeply, and it’s impacted my life in the most positive way possible.
Here’s what I’ve learned about love in the last 6 months.
“The reason to win the game is so that you can be free of it.” — Naval
It started with some tweets.
Twitter (now X) has changed my life in ways that I had never expected.
I recently paid $84 for the premium subscription (meaning I’ve got a little blue checkmark on Twitter now), but I really see that investment as a bit of a thank-you for all that the app has given me in the last 12 months.
It all started last summer when I became very “bullish” on the potential of Twitter as a writing app. I saw people writing threads and going viral and plugging coaching services, ebooks, and digital products, and as someone who’s always been interested in digital entrepreneurship, I started using Twitter more, hoping that eventually, the app would help me make money.
That was the whole reason I started using Twitter. I just wanted some Wi-Fi money. I definitely didn’t expect to make friends or build a network of like-minded people, and I definitely didn’t expect to find the woman that I love and now call my girlfriend on Twitter of all places.
But hey, Twitter beats Tinder every day of the week.
If there’s anything that I’ve learned in the last year, it’s that life is crazy and you often find the best things when you’re not looking for them.
I didn’t get what I set out for, but I got what I really wanted.
The way my Twitter account started to grow came from when I started tweeting about Jiu-Jitsu. Here’s an article on growing on Twitter, if that’s something you’re interested in.
But back to my story.
The first time I think MJ and I started going back and forth was in November of 2022. I posted about being in LA for a competition. She replied and said I needed to go to San Diego, to get “the best Mexican food ever”.
We still argue about Mexican food to this day, because as a non-Mexican and Chipotle regular, I definitely know where the best Mexican food in the country is. (Please note the sarcasm.)
Anyway, over the next few months, sporadic interactions between me and MJ became more frequent, and then eventually, one thing led to another and we started chatting off Twitter. It was right around the time when I was “becoming a cowboy” and spending the months of April/May training in Austin, where I would eventually move.
She decided to fly out from California and spend a weekend with me, and although it was not that simple, the rest, as they say, is history.
I do know this: that weekend that she came out was my favorite weekend for the entire time I was in Austin this spring.
But Rome wasn’t built in a romantic weekend.
At this point in my life, I’m wise enough to know that good relationships take time to build, but I’m intuitive enough to know that you have to take risks to get the things you want.
If you want to be with someone, you need to invest — time, energy, and money — to show that you want to be with them and to prove that you want to be with them. For MJ and I, since we’ve been doing a long-distance relationship, this has been extremely true. Part of what I believe has made our relationship so strong is that we’ve both put in a lot of effort to make it work, despite the distance and other factors that could have pit us against each other time after time.
When we have conflict, we do a really good job of working as a team, instead of as individuals trying to “win”. This is something I had never experienced before.
Relationships — like Rome, one of the many places she and I have traveled to together — are not built in a day, week, or month. Relationships are a neverending dance. There are good days and bad days, and a good relationship is built by transcending the bad days and enjoying the good ones. It’s not a highlight reel, it’s just real.
I like that.
You can feel the poetry, but you can’t see it because you’re living it.
That’s why it’s smart to zoom out every once in a while and just remember. Gratitude is a prerequisite for love that most people forget.
A note on the dating culture and success.
Since I began my relationship with MJ, I’ve noticed a few things that have made me realize what good relationships are really like that I didn’t know before.
Here are 3 of the most important lessons:
First of all, a good relationship should not distract or detract from your ability to live your best life. You should still be able to do good work, you should still be able (and encouraged) to take chances toward big goals, and you should feel safe to fail. In the past, I’ve not felt this way in relationships, and that’s why I’ve spent a lot of my time choosing to be single.
Having my girlfriend in my corner while I moved halfway across the US to chase a crazy grappling dream has been the backbone of much of my success and stability in the last 6 months.
Second of all — and this is very important — today’s dating culture does not prepare people to have good relationships. It’s preparing us to have many relationships. Today’s dating culture is based on the abundance of partners but the scarcity of connection. People just give up when sh*t gets hard.
It’s best to leave this culture and the beliefs that encompass it. It does not serve you and it will not make you happy. It will make you resentful.
Third and finally, love is not a feeling, it is an action. For example, when someone tells me they “love Jiu-Jitsu” but don’t actually spend time practicing it, I am suspicious about the authenticity of their love. Likewise, when someone is in a relationship with someone, it’s their actions that speak far louder than their words.
As a writer, this is a bit of a bummer. I’m good with my words, but I’ve had to learn over the last few years to be equally as good with my actions. I’m still a work in progress.
Here’s a simple idea that I’ve learned that helps me — and I find that it applies to everything in life:
Do your best to do what you say you’re going to do.
Simple, not easy.
Closing Thoughts
I don’t write about relationships much because they still give me a bit of anxiety.
Although MJ has helped me begin to break free of beliefs that I’ve held based on years of living in “the modern dating culture”, there’s still a part of me that fears the rug pulled out from under me. I hope that one day, with time and love, that fear will go away — or at least ease a bit — but until then, I have to keep doing the work.
That’s what I really think is “the dating habit of winners”. Winners put in the work on their relationships the same way that they put in the work on their skills. Every day, I sit at my computer and hammer out writing. Likewise, every day, I show up to the gym and put in the work on my Jiu-Jitsu and my fitness.
My relationship is similar — although I must admit, it’s far less painful than training twice a day every day or trying to come up with engaging writing ideas 7 days a week.
The work required for a good relationship is necessary, but it should never feel like a chore.
A relationship is like a plant — but not a cactus. If you neglect your relationship, it will die. Winners know that you can’t “win a relationship”, but you can lose one.
The reason to play the game is to be free of it.
Right now, I feel like I’m playing with a lead.
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