You’re putting in the work. You’ve updated your profile, you show up to dates, you’ve read enough about attachment theory to teach a class. And yet here you are, still looking.
The problem probably isn’t you. It’s where you’re putting the effort.
Most dating advice is about presentation: How you look, what you say, how you come across.
Very little of it addresses the structural questions: How many new people are actually entering your life each week? Are you visible enough for the right person to find you? Are you staying in relationships past the point where you already knew? Are you protecting yourself from embarrassments so small they don’t deserve protecting against?
These are the questions that actually determine outcomes, that most people never think to ask.
The people who find great relationships fastest are usually not the most attractive, the most interesting, or the most emotionally evolved. They’re the ones who understood something structural about dating that everyone else is too busy optimizing the wrong things to notice.
You don’t want to date hundreds of people. No one wants to casually date forever. What you really want is to date “your person” who’s for you next, get off the apps, and never date again. That search for “the one” can encourage people to try to be a bit too perfect and precise. They wait too long, they overscreen and filter out potential partners too stringently. Their vetting process is thorough and they treat every first date like a high stakes interview.
Here’s the thing: Is your filter really that good? Is your discernment calibrated that well?
Probably not. The best way to improve your filtering ability is with reps, not reflection. You can’t think your way to expertise. You can’t calibrate what you want from someone by thinking harder about it. You calibrate it by dating badly a few times and noticing what breaks things.
You need to date more initially, to date less in the long run.
Trying to be too finely tuned and too perfect from the start makes everything take longer.
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Most dating advice focuses on how you show up: your profile, your photos, your opening line, what you say on the date. Almost nobody thinks structurally about the raw number of new people they’re physically near each week. That number, for most people, is embarrassingly low. We’re creatures of habit, so our worlds are actually quite small. Same friends, same neighborhood, same grocery store, gym, coffee shop, all at the same times on the same days. Not to mention we get on the same apps, with the same pictures, and same profile, ironically hoping for different results. The number of people in your orbit is a hidden bottleneck.
The fix isn’t going to more singles events. It’s re-engineering your routines to leverage proximity. Mix up your patterns. Go to some of your same places, on different days or at different times. Go to different places altogether. Join a running club, a ceramics class, a monthly comedy night you actually commit to. Not because any individual person there is your person, but because you need to be near new people repeatedly, not just occasionally.
Real relationships grow from accumulated familiarity,
not a single charged encounter.
Imagine being at a wedding, and the bride and groom turn to you and, in front of everyone, thank you for helping bring them together. Goosebumps. Who wouldn’t want to play a role in getting two people together? No one. That’s why you have to put that energy out into the world more.
It’s as simple as saying, “I’m genuinely open to being set up if you think of anyone.” It’s not awkward. It’s a compliment. You’re telling that person that you trust their judgment and think they know great people. They’ll be flattered, and then they’ll immediately get to work.
Don’t just rely on your close friends. It’s tough for them because you know the same people. Instead, the real opportunity is with casual acquaintances. Your college roommate’s coworker. The woman from your gym. The person you met at a wedding two years ago and connected with on Instagram. Their networks are completely different and full of people you’d never encounter on your own.
That’s wonderful, but for your online dating profile or a first date, it’s terrible. Here’s why: Everyone loves to travel. Because you appeal to everyone, you capture the attention of no one.
The same goes for loving your family, being adventurous, foodie, hiking, wine lover, brunch, beach, fitness, yoga, dog mom,…you get the idea. The same goes for cute phrases like, “Works hard, plays harder.” (Just don’t).
Potential partners really all of this the same way: I don’t need to meet you because I already know you (and have met someone just like you before). These descriptions make you boring. You’re not boring.
The people who are most captivating are specific. They stick out, they’re hard to forget. Quirkiness gives you an advantage. Not in a weird way, but show what makes you stand out. The corporate lawyer who competes in powerlifting. The grandma who also kite-surfs. The former CIA agent who’s also a dancer. The teacher who spent a year in rural Japan and came back with a ceramics obsession.
The details don’t have to be dramatic. They have to be real, and distinct enough that the right person reads them and thinks: Huh…that’s someone I need to meet.
Bonus: Make sure the way you describe yourself will sound unappealing to some people. That means the people who aren’t for you, aren’t wasting your time.
As humans, we’re highly sensitized to even the smallest embarrassments. Ever had this happen? At a restaurant, your server brings your food and says, “Enjoy your meal.” And you respond, “You too.” Just me? Cool. I still think about it.
In dating, we fiercely protect ourselves from the embarrassment of rejection, looking too eager, seeming needy, or saying too much too soon. Though it sounds natural and harmless, these concerns hold the relationship back. You might not send a text, talk to someone at a party, make eye contact and say “hey” to a cute stranger, flirt enough, or show someone how much you’re actually interested. That’s a lot of inaction and playing small.
Look at the consequences. Sending the text costs almost nothing. Not sending it costs a potential relationship.
Saying you’re looking for something real on date two, might be a little awkward if they’re not on the same page. Not saying it costs months of slow-burn situationship ambiguity that ends in the same place anyway.
The downside of being direct is almost always smaller than it feels in the moment. The upside is that you stop wasting time with people who aren’t actually on board. What reads as risk is usually just discomfort. Unfortunately we prioritize immediate discomfort much more heavily than potential long-term pain.
Anyone can show up well when they’re trying. First dates, special occasions, moments when the stakes feel obvious (e.g., meeting the friends). Even the world’s worst partners know to show up then. They can fake it long enough to get by. But, that’s not actually where you learn much about a person.
You should really pay more attention in the low-stakes moments. How someone talks about their ex when they’re relaxed and not still managing impressions. How they treat a server on a Thursday night when they’re tired after a long day at work. Whether they’re curious about your day or mostly waiting to talk about theirs. These aren’t small things. They’re some of the best data you have about long-term relationship potential. Relationships have some big moments, but mostly consist of the mundane. Partner have to be great then too.
Tyler spent two years in a relationship they struggled to make work, which ultimately fell apart. Chris had five relationships over the same two years.
Which one sounds like the worse situation? Which person will have learned more about love? The fact is, five sequential one-year relationships will likely teach you more, and cost you less, than one five-year dead-end relationship with a ceiling (that you probably should have seen from the start).
“Good enough” relationships are a trap.
That’s easy to understand in theory, but hard to put into practice. Leaving a relationship feels like failure. It’s even more difficult if the relationship isn’t terrible, but merely “good enough.” (Those relationships are a trap.) Starting over feels expensive. So people succumb to inertia and continue on, staying past the point where it would have been easier to leave. Defaulting to complacency is easier than making difficult decisions.
Now, you shouldn’t jump from relationship to relationship for the fun of it. But, if you’re not finding what you’re looking for, it may be time to look elsewhere instead of hoping your partner or the situations miraculously changes. Check-in with yourself periodically: Is this relationship still headed in the right direction? Not “is this perfect” (it won’t be), but is this really what I want? You want to thrive, not just survive.
Hope this helps,
Dr. L
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Photo by Marcos H. Mujunen
Note: Please forgive any typos or errors. Non-AI writing has its imperfections. Consider it the patina of a personal touch.
