High Expectations, Loosely Held: The Mindset for Modern Dating

When I first moved to New York, I treated every date like a test I needed to ace. I’d show up already imagining the second date, the third, maybe the relationship that could come from it. I wasn’t dating a person. I was dating the potential.

I Just Wanted It to Work

When I first started dating in New York, I just wanted it to work. That was the goal every single time. I didn’t care if there was real connection. I cared if it could become something.

Even when I knew it wasn’t right, I’d still try to make it make sense. I’d tell myself the timing was off or that maybe I just needed to give it another shot. But the truth is, deep down, I already knew. It wasn’t going anywhere. I just didn’t want to admit it.

Looking back, I think I was more attached to the idea of it working than the person sitting across from me. I wanted proof that I could make something last. That I wasn’t the guy who always ended up back at square one.

That mindset might look like effort, but it’s really control in disguise. When you want something so badly, you start ignoring how you actually feel. You stop noticing the energy between you and start managing the story you’re trying to write.

Every time it fell apart, it hurt more than it should have. Not because I lost someone special, but because I lost the version of the story I’d already built in my head.

There was one time I got ghosted, and I spiraled. It messed with my confidence more than I wanted to admit. That moment turned into an episode called Getting Ghosted Hurts, But It Might Be the Best Thing That Happened to You. That’s when I finally saw what expectations do to us. They don’t create connection. They block it.

The Ted Mosby Phase

A friend once told me I was acting like Ted from How I Met Your Mother. He was right.

I wanted every date to be the one. Every coffee could’ve been the start of something big. Every text had meaning. That sounds romantic, but it’s exhausting. When you’re constantly trying to make things happen, you stop letting anything happen naturally.

And when you’re surrounded by people getting engaged, moving in together, or posting couple photos every weekend, it’s easy to start believing you’re behind. That kind of comparison sneaks in quietly. It makes you feel like love is a race and you’re losing.

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

But 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 too. I’d try to sound like the perfect candidate instead of a real human being. That’s why I made Stop Sounding Like a Robot in Job Interviews. The same lesson applies in dating: 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 my entire dating life for a while. I could feel when something wasn’t right. When the energy was off. When the conversation felt like work. 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 out of willpower. But when you want it to work badly enough, you start ignoring what your gut already knows. You make excuses for the distance, the slow replies, the weird energy. You convince yourself that if you just try harder, it’ll click.

Letting go felt like failing. But once I actually did, it felt like relief. I stopped waiting for someone else to validate the effort I was putting in.

That’s when dating started to feel lighter again.

What Actually Changed

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

That sentence still feels true. Lowering expectations wasn’t about caring less. It was about being honest with myself.

I stopped walking into every date looking for a potential relationship. I started paying attention to whether I even liked how I felt around the person. Was I comfortable? Did I feel understood? Could I actually be myself?

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

It’s the same mindset I talked about in Ruin the Friendship. Learning to take a step without knowing the outcome. When you stop gripping so tightly to how it should go, you actually make space for something real to show up.

You Don’t Know Her Yet

I said this in the episode, and it’s still one of my favorite lines:
“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 it. 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 go in already imagining the outcome, curiosity disappears. You stop listening. You start projecting.

She might be seeing other people. She might not even know what she wants. That’s fine. None of it’s personal.

Notes from Josh

For years, I thought effort could fix anything. That if I just cared enough, it would eventually work.

But the truth is, 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 was about rebuilding confidence, this one is about learning to stop forcing what isn’t meant for you.

Because dating isn’t about finding someone perfect. It’s about finding someone real.

Read next on Guyset.com:

• Ruin the Friendship — why taking a risk might be exactly what you need

• Getting Ghosted Hurts — how to detach from rejection

• Stop Sounding Like a Robot in Job Interviews — the confidence crossover between dating and career