How to Handle First Dates Without Getting Ahead of Yourself

Q: 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.”

You can’t know after one date if she’s your person. That’s the whole point. It’s an introduction, not an interview. When you stop trying to make it work, you actually see what’s real.

Related read: High Expectations, Loosely Held — how letting go of control makes dating fun again.

Q: 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,” I said.

That’s not just about texting. It’s about how you view yourself. Reaching out shows interest, not weakness. Confidence isn’t waiting for someone to validate you. It’s acting from a place of calm, not fear.

More confidence reads:

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

• Stop Sounding Like a Robot in Job Interviews — the same mindset shift that applies in dating too.

Q: 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.

My friend once told me I was acting like Ted from How I Met Your Mother. And 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’s the shift. Dating isn’t about predicting the future. It’s about staying present long enough to find out if there even is one.

Explore more from Guyset Dating: 7 Lessons from “Dating Expectations” — how to approach early dating with curiosity instead of pressure.

Q: 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,” I said. “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 start convincing yourself that maybe she’s just busy or bad at texting.

But no one is too busy for something they want.

It’s not about blaming her or yourself. It’s about recognizing when you’re forcing something that isn’t mutual. Pulling back isn’t losing. It’s making space for something real.

Want to go deeper? Getting Ghosted Hurts, But It Might Be the Best Thing That Happened to You on how rejection can actually build confidence.

Q: 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.

That one sentence changed how I date.

Lowering expectations doesn’t mean lowering standards. It means holding them loosely. You can want a real connection without gripping it so tight that it breaks. 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 fine.

Read next: High Expectations, Loosely Held.

Q: What if I feel like I’m 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,” I said. “Especially when you’re out of college and you see friends in relationships, and you start to see people getting engaged.”

It’s easy to feel like you missed the train. But dating isn’t a timeline. There’s no scoreboard.

When I was trying so hard to make things work, it was mostly because I didn’t want to be the one still figuring it out. I didn’t want to feel like the last single guy in the group chat.

But that mindset just makes everything heavier. The right person fits into your life when it’s full, not when it’s empty.

Also read: The Comfort Test: How to Know If You’re Ready for a Real Relationship.

Q: How do I stay confident through all the 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.”

That’s not just a quote from the episode. That’s the whole point of this podcast.

For a long time, I thought rejection meant something was wrong with me. Now I see it for what it is, and that's redirection.

Every no brings you closer to the right yes. Every awkward conversation teaches you something about what you actually want.

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

The Bottom Line

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

If you’re overthinking, replaying, and clinging, it’s probably because you just want it to work. I get that. But the right connection doesn’t need convincing.

So keep showing up as yourself. Be curious. Be honest. Be open. But don’t make your self-worth depend on someone else’s response.

Because when you stop chasing approval, you start attracting alignment.

Related Reads

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

• 7 Lessons from “Dating Expectations” — mindset shifts that actually make dating fun again.

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