The Toolkit by Guyset Issue #3 | The Unwritten Rules of First Dates

Nobody teaches you how to go on a first date. There's no rulebook, no playbook, and no guide to what actually works. So I made one.

By
Josh Felgoise

Spider-Man: Brand New Day

Let's Get Into It

There are a lot of things in life that nobody actually teaches you.

No one sits you down and explains how to go on a first date, what to text beforehand, how to calm your nerves, or what actually makes someone want to see you again. Most of us just figure it out through trial and error.

This week's episode is about changing that.

I wanted to create something that feels like the guide I wish every guy had before his next first date. Not because there are perfect rules, but because a little bit of preparation creates a lot more confidence.

And confidence is usually what makes the date go well.

"The biggest thing about knowing a little bit more about what to do... is the confidence that knowing a little bit more gives you."

This Week's Episode

This week I introduced a new Guyset series called The Unwritten Rules.

The idea is simple: there are situations everyone experiences but almost nobody explains. Dating is probably the biggest one.

In this episode I break down everything from confirming the date that morning, getting ready, arriving early, asking better questions, paying for the date, following up afterward, and the small things that leave someone feeling excited to see you again.

The goal isn't to memorize a script.

The goal is to remove uncertainty so you can actually relax and be yourself.

The Main Thing

If you only remember one thing from this week's episode, make it this:

Confirm the date the morning of.

Around 10:00 or 11:00 a.m., send a simple text.

"Hey! Just making sure we're still on for tonight. Looking forward to seeing you."

That's it.

It seems small, but it changes the entire day.

Instead of wondering whether the date is still happening, both of you get to spend the day actually looking forward to it.

You're replacing anxiety with anticipation.

"You're creating an energy for this date that we're both excited for it."

It's such a small habit, but I genuinely think it separates guys who are intentional from guys who just hope everything works out.

Three Things I'd Remember Before Every First Date

Every episode usually has a few big takeaways, but these are the three I'd actually want you to remember.

1. Confirm the date that morning.

Don't leave someone wondering if tonight is still happening.

2. Ask questions.

If conversation feels awkward, curiosity fixes almost everything.

People like talking to people who are interested in them.

3. Make sure they got home safely.

Whether you want a second date or not, sending a quick text afterward is simply the right thing to do.

Those three things take less than five minutes combined, but they completely change how the experience feels.

If You're Going On A Date This Week...

Here's one thing I'd keep in mind:

Your goal is not to impress them.

Your goal is to discover whether the two of you actually enjoy spending time together.

That's a completely different mindset.

When you stop treating the date like a test you have to pass, you naturally become more relaxed, ask better questions, laugh more, and show more of who you actually are.

Ironically, that's usually what makes someone want another date.

Try This

The next time you have a first date, follow this simple checklist:

  • Confirm the date around 10 a.m.

  • Shower, trim your nails, wear clothes you feel confident in, and smell good.

  • Arrive five to ten minutes early.

  • Ask one extra follow-up question every time the conversation gives you the opportunity.

  • Before you go to bed, text to make sure they got home safely.

None of these are complicated.

They're just the little things that make dating feel easier.

Question For You

"What's the biggest mistake guys make on first dates?"

Trying too hard to say the perfect thing.

The best conversations rarely happen because someone had the perfect line.

They happen because someone was genuinely curious, listened well, and made the other person feel comfortable.

The less you're performing, the more you'll actually connect.

Three Things I'm Into This Week

A simple confirmation text.
It might be the easiest way to reduce first-date anxiety for both people.

Asking better follow-up questions.
The best conversations usually come from the second question, not the first.

Doing the small things consistently.
Showing up early, putting your phone away, and checking they got home safely won't guarantee chemistry, but they'll always make you someone worth going on a date with again.

One Last Thing

One line from this episode really captures why I wanted to make it:

"You will leave this episode feeling more prepared for your next date... and more confident about what you're going to do."

That's really what Guyset is about.

Not giving you a script.

Giving you enough clarity that you can stop wondering what to do and start enjoying the experience.

I'll see you next Tuesday.

— Josh

Read more on Guyset:

  • What to Say to Confirm the First Date (Exactly)

  • How Early Should You Arrive for a First Date?

  • How to Start a Conversation on a First Date