How to Handle First Dates Without Getting Ahead of Yourself

How Do I Stop Replaying Every Second of the Date in My Head?

Trust me, I’ve been there. I used to walk home from dates replaying every moment like a highlight reel. Did I talk too much? Was I funny enough? Did I ask enough questions?

For me, that overthinking always came from one place: I just wanted it to work.

The problem isn’t caring too much. It’s expecting too much.

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

That mindset was exactly what I unpacked later in High Expectations, Loosely Held, because you can’t know after one date if someone is your person. That’s the whole point. A first date is an introduction, not an interview. When you stop trying to make it work, you finally see what’s real.

What if she doesn’t text me first? Should I reach out?

Yes. If you want to, reach out. But don’t spiral about it.

I said in the episode, “Everyone’s phone is within reach and it’s charged and ready to go at all times.”

That’s true. If someone wants to talk to you, they will. And if you want to talk to them, you should.

What you can’t do is attach your self-worth to whether or not they respond.

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

That’s not just about texting. It’s about how you see yourself. Reaching out shows interest, not weakness. Confidence isn’t waiting for someone to validate you. It’s acting from a grounded place, which is the same core idea behind Ruin the Friendship and why taking the first step builds confidence instead of destroying it.

There’s also a real psychological reason this spirals so fast. Psychology Today breaks down how rumination fuels anxiety and overthinking in dating, especially when silence leaves room for interpretation.

How do I stop assuming every first date could be the start of a relationship?

This was me for years. I’d meet someone, feel a spark, and immediately start building a story in my head.

It wasn’t about the person. It was about the potential. I wanted it to work so badly that I skipped the part where I actually got to know them.

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 said. “It’s also easier to see what someone else is doing wrong than realize you’re doing the same thing.”

When you imagine a whole relationship before you know someone’s middle name, you’re setting yourself up for disappointment.

“You don’t know her at all,” I said. “You don’t know her middle name. You don’t know where she’s from. You’re just getting to know her.”

That exact shift is what 7 Lessons That’ll Change the Way You Think About Dating is built around. Dating isn’t about predicting the future. It’s about staying present long enough to see if there even is one.

What if I can tell she’s not as into it as I am?

That one hurts. Especially when you just want it to work.

“I was trying to fit a square peg in a round hole and I was trying to make it work.”

If you’ve ever done that, you know how draining it is. You start explaining away the distance, the slow replies, the mixed signals. You convince yourself she’s just busy or bad at texting.

But no one is too busy for something they want.

Pulling back isn’t losing. It’s creating space for something mutual. That’s why getting ghosted, as much as it sucks, ended up teaching me more about confidence than most good dates ever did.

How do I handle the anxiety after a date when I really like her?

That’s the hardest part. The wait.

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

Lowering expectations doesn’t mean lowering standards. It means holding them loosely. You can be excited without letting that excitement turn into pressure.

If it’s right, it’ll flow.
If it’s not, it’ll fade.

Either way, you’ll be okay.

What if I feel behind because everyone else has someone?

You’re not behind. You’re just in a different chapter.

“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.”

Dating isn’t a timeline. There’s no scoreboard. That comparison spiral is exactly what I worked through when asking How Do I Choose a Career Path When I Have No Idea What I Want?, because pressure doesn’t mean you’re late. It just means you’re paying attention.

How do I stay confident through rejection?

By remembering one thing: your worth isn’t up for debate.

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

Rejection isn’t proof you’re failing. It’s redirection.

Confidence isn’t about never getting rejected. It’s about knowing rejection doesn’t define you.

And Here's The Thing

Dating isn’t about finding someone who likes you. It’s about finding someone who matches your energy.

If you’re replaying, overthinking, and clinging, it’s probably because you just want it to work. That’s human.

But the right connection doesn’t need convincing.

When you stop chasing approval, you start attracting alignment. How Should I Respond When Someone Cancels a Date? Because you are attached to the outcome instead of the experience.

FAQs

Should I text first after a date?
Yes, if you want to. Interest is not weakness.

How do I stop dating the potential?
Stay present. You are getting to know someone, not predicting the future.

What if I like her more than she likes me?
Pulling back is not losing. It is self respect.

How do I stay confident through rejection?
By remembering your worth is not up for debate.