The A–Z of First Dates

This first date guide is for anyone who’s never had one, hasn’t had a good one, or hasn’t had one in a while.

Alright, let’s get this out of the way: first dates are awkward.

They just are.

You’re meeting someone new (maybe for the first time IRL), trying to make a good impression, all while wondering:

• Do I like them?

• Do they like me?

• What do I talk about?

• Omg, did I have food/lipstick on my teeth the entire time?

So, if it’s been a minute — or a lot more than a minute — or hell, you’ve never had a good first date, let’s walk through the whole thing from A to Z, start to finish.

Step 1: Asking Someone Out

Be direct. Seriously. You don’t need to pull off a clever setup or construct an elaborate situation where a date “just happens.” Confidence doesn’t mean you’re fearless — it means you’re willing to be clear and take a risk.

Three scripts you can borrow or remix:

• “I’d love to get to know you more. Would you like to go on a date with me?”

• “I think checking out [location] would be fun with you. Want to go together?”

• “There’s a [specific event] coming up. Are you free to go?”

Yes, it’s scary. That’s the price of entry.

Just remember — when you ask someone a question, they get to say yes or no. Obviously, you want one answer more than the other… but isn’t that the point?

👉 If you’re using an online dating app, here’s why you should do a video call first.

Step 2: Choosing Where and When

Two people reviewing a paper map together, pointing out a location — representing the collaborative process of choosing a first date location and time.

Here’s the key word: collaboration. That doesn’t mean sending 20 Yelp links and turning this into a group project — it means balancing what works for both of you.

A few things to consider:

• Make it easy. Pick a place with easy parking or transit, ideally somewhere in the middle.

• Decide what matters more — the where or the when.
  → If where matters more, offer 2–3 location options and ask them to choose.
  → If when matters more, nail down a time and then pick a place that fits.

• Pick a quiet-ish, public, low-pressure setting. Think: coffee shop, bookstore, a walk (not a hike), or a casual bite. 👉 Need ideas? Here’s a list of great first date options.

• Skip the alcohol if you want. You don’t need booze to have a good time. If bars aren’t your thing, that’s totally okay.

And one more thing — don’t over-invest. This is someone you might like. Treat it like you’re meeting a potential friend.

Step 3: What to Do During the Date

Two people laughing together outdoors, highlighting the joy, connection, and lightness that can happen on a first date — even if it starts off a little awkward.

You will be awkward. You will be nervous. You might even be sweaty.

All normal. All expected.

If you weren’t, that would actually be kind of concerning.

Think of it as extra energy and redirect it into something productive. Ever take an improv class? Here’s a quick crash course in 8 bullets:

1. Don’t comment on it repeatedly (“I’m so nervous!” — yes, we know).

2. Don’t linger.

3. Don’t spiral.

4. Stay present.

5. Share a little.

6. Ask a little.

7. Be curious about the other person’s story.

8. Assume they’re curious about yours.

There’s probably decades of interesting stuff in both of you. You’re not going to unpack all of it in one sitting — but tug on a few threads and see where it leads.

👉 Not sure what to say? Check out this guide to breaking the ice.

Step 4: Ending the Date

Sorry, I can’t guarantee zero weirdness.

What I can help with is ending the date with a bit less weirdness.

Here’s something easy to forget and plow right through: end on a high note. Even if it’s going well, don’t let it drag until you’re both tired or start repeating yourselves. I repeat: don’t!

Instead, make a comment about the time spent together and suggest wrapping up. Try this script: “Wow, this was fun — shall we head out?”

Sometimes a physical transition point helps, like going to the restroom, and then saying it when you come back.

• If you had fun — say that.

• If you want to see them again — say that.

• If you had fun and don’t want to see them again — say that.

• And no matter what — thank them for their time. Ditto if you’re on the receiving end.

You might feel pressure to figure out next steps, but you don’t have to decide anything on the spot. While many people intuitively know if they want to see someone again, that can change while driving home or after a night of sleep. Listen to your intuition, but don’t rush it.

Step 5: What to Do After the Date

If you both agreed to talk more or go on a second date — great! Go back to Step 1 above.

If one of you changed your mind afterward — say something.

If you want to go on a second date but didn’t bring it up in person — say something.

Two things I suggest you don’t do:

• Ask for a post-date performance review (“Did you have fun? Did you like me?”)

• Start a meta-conversation about what the date meant. You’re not there yet.

👉 Worried about ghosting or being ghosted? Here’s how to understand and handle it.

Final Thoughts

Dating is vulnerable. First dates are awkward. But they can also be a chance to be brave, curious, and real with someone new.

Be clear. Be kind. Be collaborative.

And remember: it’s not about winning someone over — it’s about seeing if you connect.

Want Help Navigating Your First Dates?

A quiet moment with coffee and a laptop — space to reflect, plan, or connect.

Whether you're getting back out there after a break or gearing up for your very first date, I offer 1:1 coaching to help you build clarity, confidence, and connection without overthinking every little move.

If you're feeling stuck, nervous, or just want a second brain on your dating life, I’m here for that.

📩 Email me at Info@DateLabHQ.com to ask a question or book a free intro call.

Let’s make your next first date feel a little less overwhelming.