High Expectations, Loosely Held: The Mindset for Modern Dating

I Was Dating the Potential, Not the Person

When I first moved to New York, I treated dating like something I needed to get right.

I’d walk into first dates already imagining the second. The third. Maybe even the relationship that could come from it. I wasn’t meeting someone where they were. I was projecting where I hoped it would go.

I wasn’t dating a person.
I was dating the potential.

I Just Wanted It to Work

When I started dating in New York, my only goal was simple: make it work.

Not feel it out. Not see how it went. Make it work.

Even when I could tell something wasn’t right, I’d keep pushing. I’d tell myself the timing was off. Or that maybe I needed to give it another shot. Deep down, I already knew. It wasn’t going anywhere. I just didn’t want to admit it.

Looking back, I wasn’t attached to the person. I was attached to the idea that I could finally make something stick.

I wanted proof that I wasn’t the guy who always ended up back at square one.

That mindset looks like effort, but it’s really control. When you want something badly enough, you stop listening to how it actually feels. You start managing the story instead of paying attention to the energy.

And when things fell apart, it hurt more than it should have. Not because I lost someone special, but because I lost the version of the future I’d already built in my head.

That realization hit hardest after getting ghosted. That experience eventually turned into What To Do When You Get Ghosted (And What It Actually Says About Them), because expectations don’t create connection. They block it.

The Ted Mosby Phase

A friend once told me I was acting like Ted Mosby. He wasn’t wrong.

I wanted every date to be the one. Every coffee had meaning. Every text felt loaded. That sounds romantic, but it’s exhausting.

When you’re surrounded by friends getting engaged, moving in together, or posting couples photos every weekend, it’s easy to feel behind. Comparison sneaks in quietly. Suddenly dating feels like a race and you’re losing.

So you grip tighter to things that don’t fit. You convince yourself that effort equals connection. You ignore red flags and amplify the maybes.

Psychologists actually talk about this exact pattern. According to Psychology Today, dating someone’s potential instead of their present behavior often comes from anxiety around being alone, not genuine compatibility.

Dating isn’t supposed to feel like a performance review. It’s supposed to feel like curiosity.

I used to do the same thing in job interviews. I’d try to sound perfect instead of human. That’s why Why Sounding “Too Prepared” Is Ruining Your Interviews exists. The lesson is the same. People don’t fall for perfection. They fall for presence.

Trying to Force It

“I was trying to fit a square peg in a round hole.”

That line sums up a whole chapter of my dating life.

I could feel when something was off. When conversation felt like work. When the energy wasn’t there. But I’d still try to fix it. I’d rewrite the story in my head until it made sense.

You can’t build chemistry with willpower. But when you want it to work badly enough, you start ignoring what your gut already knows.

You excuse the slow replies.
The weird distance.
The lack of effort.

You tell yourself that if you just try harder, it’ll click.

Letting go felt like failing. But when I finally did, it felt like relief.

That’s when dating stopped feeling heavy.

What Actually Changed

“When I started lowering my expectations, I was so much less anxious about trying to make it work.”

Lowering expectations didn’t mean caring less. It meant being honest.

I stopped walking into dates looking for a relationship. I started paying attention to how I felt around the person.

Was I comfortable?
Did I feel relaxed?
Could I actually be myself?

When you focus on that, dating stops being about proving something and starts being about discovering something.

This is the same mindset shift I talked about in High Expectations, Loosely Held, where pressure kills connection and space lets it breathe.

You Don’t Know Her Yet

This line grounded me more than anything:

“You don’t know her at all. You don’t know her middle name. You don’t know where she’s from. You’re just getting to know her. That’s the point.”

That’s dating.

You’re not supposed to know everything after one drink or one walk home. You’re supposed to be curious.

But when you walk in already imagining the ending, curiosity disappears. You stop listening. You start projecting.

She might be seeing other people.
She might not know what she wants yet.

None of that is personal.

It’s just early.

If early-stage uncertainty makes you spiral, Why Does Rejection Hurt So Much After Just A Few Dates helps you stay grounded instead of getting ahead of yourself.

Notes from Josh

For a long time, I thought effort could fix anything. That if I just cared enough, things would eventually work.

But the right thing won’t need convincing.

Lowering expectations doesn’t mean lowering standards. It means letting go of control. Because when you stop trying to plan the perfect outcome, you finally give the right one room to show up.

If Ruin the Friendship was about taking the first step, and Getting Ghosted Hurts, But It Might Be the Best Thing That Happened to You was about rebuilding confidence, this one is about learning to stop forcing what isn’t meant for you.

Dating isn’t about finding someone perfect.
It’s about finding someone real.

FAQ

Why do I get attached to potential so quickly?
Because hope feels safer than uncertainty. But real connection comes from presence, not projection.

How do I stop forcing dating outcomes?
Focus on how you feel in the moment, not where it could lead.

Is lowering expectations the same as settling?
No. It’s lowering pressure, not standards.

How do I know when something isn’t right?
When effort feels one-sided or you don’t feel like yourself around them.

What’s the biggest dating shift you made?
Stopping the need for it to work and letting it unfold instead.