7 Lessons That’ll Change the Way You Think About Dating

When I first started going on dates, I just wanted things to work. Every time. I’d overthink every detail, what I’d say, what I’d wear, how I’d act, as if that could control how it ended. But trying to manage every moment doesn’t create connection. It kills it.

“It’s important to have high expectations about what this could potentially be, but loosely hold those high expectations.”

That one line from the episode became my new mindset. When you stop forcing things and start paying attention, dating stops being a test and starts being fun again.

Here are seven lessons that changed everything.

1. You Can’t Control Chemistry

“I held my expectations so high for every girl that I met in the beginning. I kind of came with these things I wanted with each person on every date.”

That quote sums up my old dating life perfectly. I went into every first date already assigning meaning to it. I wasn’t meeting people. I was auditioning them.

If I’m being honest, I just wanted it to work. Every time. Even when it didn’t feel right. I thought the right combination of conversation and confidence could make chemistry appear.

But chemistry doesn’t come from checklist compatibility. It comes from ease. From being present enough to notice what’s real instead of trying to manufacture it.

I learned that the hard way in Getting Ghosted Hurts, But It Might Be the Best Thing That Happened to You. Rejection isn’t always failure. Sometimes it’s feedback. Sometimes it’s proof that chemistry can’t be controlled.

2. Don’t Be a Ted Mosby

A friend once told me I was acting like Ted from How I Met Your Mother. He wasn’t wrong.

“It’s so much easier to throw stones at other people’s houses than look at your own.”

I could analyze everyone else’s dating patterns but never my own. I was always chasing connection but also trying to choreograph it. When your friends start pairing off, it’s easy to treat dating like a race. You start seeing each person as a potential finish line instead of just a person.

That mindset creates pressure where there should be curiosity. It turns connection into performance.

It’s what I explored in Ruin the Friendship. Real confidence isn’t control. It’s honesty.

The lesson: stop performing. Start connecting.

3. Lower Pressure, Not Standards

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

That was the turning point for me. Lowering pressure isn’t giving up. It’s giving yourself space to breathe.

You can still want something real without needing it to prove anything. You can still have high standards without expecting perfection.

The moment I stopped trying to prove that every date could turn into something serious, I started to enjoy them more. The anxiety faded because I wasn’t gripping the outcome so tightly.

That same shift showed up in How to Overcome Gym Anxiety: One Step at a Time. Confidence comes from progress, not perfection. The same rule applies in dating.

4. Read the Room, Not the Future

“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 line always stops me because it’s so obvious and so easy to forget.

For a long time, I’d walk into every date already imagining the ending. I’d picture the second date, the third, the relationship that might follow. I wasn’t dating the person in front of me. I was dating the story I wanted it to become.

But you can’t read the future. You can only read the room.

Notice if you feel relaxed. Notice if conversation flows. Notice if you like who you are when you’re with them. That’s where clarity comes from.

It’s the same mindset I wrote about in High Expectations, Loosely Held. Focus on what’s actually happening, not what you’re hoping to find.

5. Stop Forcing Connection

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

That’s every situationship I tried to justify.

When someone’s interest doesn’t match your effort, forcing it won’t fix it. It only drags it out. You can’t make someone like you. You can only make peace with what they’re showing you.

I used to ignore that because I wanted it to work. I’d overexplain, overanalyze, and hold on long after the spark was gone.

But when you stop trying to control the outcome, you start enjoying the process.

The moments where you feel most like yourself are what real connection feels like.

6. Comparison Is a Distraction

When you’re single and your friends are coupling up, it’s easy to panic. You start thinking something must be wrong with you.

“I think there’s a lot of guys who are like that. Especially when you’re out of college and you see friends in relationships, and you start to see people getting engaged.”

That mindset can mess you up fast. Dating isn’t a timeline. There’s no scoreboard.

For a while, I measured progress by proximity. How close I was to where everyone else seemed to be. That always ended in disappointment.

You’re not behind. You’re just early in your story.

That same truth connects Getting Ghosted Hurts and Ruin the Friendship. You can’t compare your chapter one to someone else’s chapter ten.

7. Protect Your Self-Worth

“Don’t tie your entire self-worth to someone else’s approval or acceptance of you.”

That’s not just a quote. It’s the foundation of everything.

The best relationships I’ve ever had came after I stopped needing them to validate me. Confidence doesn’t mean arrogance. It means being grounded enough in your own life that love becomes an addition, not a lifeline.

Rejection doesn’t erase your value. It redirects your energy.

When you stop chasing validation, you start attracting alignment.

The Takeaway

Dating in your twenties isn’t supposed to be perfect. It’s supposed to teach you.

Every awkward text, every almost-relationship, every unanswered message gives you feedback about who you are and what you actually want.

When you stop trying to make every date work and start focusing on whether it feels right, everything changes.

That’s what this episode was about: holding high expectations loosely and realizing that confidence doesn’t come from control. It comes from trust.

Keep Reading

• High Expectations, Loosely Held — how I learned to stop forcing connection

• Practical Q&A: How to Keep Your Cool After a First Date — real talk about texting and timing

• Ruin the Friendship — the confidence episode that started it all

• Getting Ghosted Hurts — why rejection might be the best thing that ever happened to you