School of Dating · Week 6 · Session 11

First Dates.

Low stakes, high curiosity — you can be confident and truly enjoy first dates.

Kait Tomlin × JJ Tomlin

The Foundation

A first date is not that serious.

It’s LOW stakes. You can hang out with just about anyone for 60–90 minutes, right?

Quick gut-check — on a scale of 1–10, how comfortable are you on a first date?

The Goal

Go A to B — not A to Z.

One question decides everything: “Do I know enough to want to see them ONE more time?” That’s it. That’s the whole assignment.

Read your Godfidence list — before AND after the date.

Read your Dating Mission Statement before you go.

Mindset · Session 7 Callback

Walk in free.

LadiesWalk-Away Power — the L in P.E.A.R.L.Surrender the outcome before you go. You do NOT need this man to like you, or to ask you out again. No performing.

MenThe Warrior — pursues, initiates, risks the no.The anti-warrior is the “sometime” man: vague, orbiting, paralyzed by fear of rejection.

Making the Ask · Men

If it’s a date, call it a date.

Not a hangout. The Warrior asks her out by name, by Friday — no ambiguity. Culture put the pressure on the word “date”; YOU set the tone for how serious it is.

Making the Ask · Men

The ask, step by step.

ConfidenceYou’re not trying to “win” her — you’re offering her a chance to know you too.

ClaritySimple, clear invites beat overthought words. Then suggest a real date right after.

AuthenticityCuriosity, not desperation. Release the result.

And you plan the date — with a safe way out for her. Safety is a woman’s love language.

Showing Interest · Ladies

Drop the hanky.

This is NOT asking him out. It’s letting him know you exist — signaling through body language and curiosity that you’re ready to receive his initiation. And yes… flirt with him.

Showing Interest · Ladies

In person: three moves.

1 · ProximityGet near him. He can’t initiate toward someone he never sees.

2 · FlirtWarm, playful, present.

3 · Green light“If you were to ask me out, I’d totally say yes 😉”

Or send a birdie — a wingwoman who drops the hint that you’d say yes.

Showing Interest · Online · Session 9 Callback

Five messages to meet.

Do NOT text for two weeks on end. A few days max, then move it to FaceTime or a phone call. Momentum is the whole game online.

The First Date Guide

Before. During. After.

Repeat after us: you can be confident and truly enjoy first dates.

Before · Where To Go

The don’ts.

Coffee sitNext to kids studying and job interviews? Romantic. Take the coffee on a walk instead.

Dinner & drinksIt’s what everyone does — boring AND expensive.

MoviesYou can’t interact at all. Out.

Before · Where To Go

The do’s.

InteractiveCooking class, museum — learning together intensifies bonding.

ActiveMove together. Guys — our best talks are shoulder-to-shoulder, not 1:1 across a table.

Unique to themWhat do you already know about them? Build the date around it.

Guys: ask her if she has a preference — it shows you care what she actually wants.

Before · Where To Go · Ladies

You have a say — even in your feminine.

Jayme: “I used to do WHATEVER the guy wanted. Once I spoke up I’ve been to mini golf, a speakeasy, an escape room, ax throwing, an enchanted garden…”

“Thank you for planning this — I’m so excited. I feel really connected on active dates. Would you be open to a hike instead?” An invitation for him to win, not a shutdown.

Before · What To Wear

What not to wear.

Anything distracting or uncomfortable — short skirts, ridiculous heels, too revealing.

Clothes that don’t fit — guys, if you’re an L, wear an L.

Heavy makeup or heavy cologne — this isn’t a wedding.

Workout clothes (yes ladies, athleisure counts) — unless the date IS the gym.

Skipped hygiene — shower, teeth, nose hairs, deodorant. Non-negotiable.

Before · What To Wear

Wear what makes you feel like a 10.

Have a go-to: ladies, that dress or jeans. Guys, keep it simple — black on black never fails.

Match the date — walking date ≠ heels.

Build 2–3 go-to date outfits so there’s never a meltdown.

Full Men’s & Women’s Style Guides are in your bonus materials.

During · Questions

This is not a job interview. (Or a spiritual one.)

“What do you do? How much do you make? Do you have debt… a 401K?”

“Do you want kids? How many? How soon are you looking to get married?”

“What’s your childhood trauma? Your testimony? Your enneagram?”

“Have you ever looked at rings?… would you like to know my ring size?”

Take the pressure OFF. You don’t have to marry this person — you don’t even have to see them twice.

During · Questions

Ask 3–5. Stay curious.

“Where are you from — and what did you like about growing up there?”

“What are your top 3 things to do on a weekend?”

“What do you love most about your faith?”

“This last year in one word — what is it, and why?”

“What made you smile today?”

More than the answers — watch how they engage back. What lights them up? (Full list + JJ’s this-or-that master list: Best Questions guide.)

During · Length

90 minutes or less.

It’s a safeguard — limits total emotional infatuation.

Leaves them curious.

Have plans after — and say so up front. That’s your bumper.

After · The 3-Date Rule

Give it 2–3 dates.

Some people are shy. Some are nervous and not themselves on date one — stressed from work, or really attracted to you and rattled by it. You will not meet the REAL person on date one. Unless there are glaring red flags, give them another shot.

After · Texting

The after-text.

LadiesThank-you text right after — even if there’s no date two.Stay in your feminine: “I had such a wonderful time — you have a way of making me feel ___.”

MenWarrior initiation — lock in.Thank her ASAP. Want date two? Say so, and follow through soon with a plan. Do NOT offer it if you’re ambiguous.

This Week

Homework.

1Ask someone out this week — or ladies, move an online chat to a phone call.

2Write your 3–5 first-date questions.

3Pick your classic first-date outfit and share it with the group.

“I want to meet and get to know someone completely different from myself — and appreciate the way God created them to be.”