When you go on a first date, so many questions run through your head.

Will he like me? Will I like him? What if we have nothing to say to each other? What if I say the wrong thing?

Those questions keep circling in your mind, making you feel sick with worry.

How am I going to make him like me? How am I going to escape if he’s awful? What am I going to tell my friends if this goes nowhere?

The challenge of pulling off a successful date is SO enormous, and SO overwhelming, that it’s hard to know where to start.

Would it help if I gave you a clear mission for that first date?

Your mission, should you choose to accept it, is to get three pieces of information from him.

By the end of the date, you should know the answers to the three questions I’m about to give you.

Now, this is not your typical first date conversation.

These questions spark off a revealing and highly personal discussion that helps you understand whether he’s someone who fits into your life.

Plus, he ends up feeling like he’s met someone who gets him on a completely different level.

Whether or not your first date turns into a second is not the point. What matters is that you’ve made a connection.

Don’t Ask These Questions

Most people don’t know the right questions to ask on a first date.

It’s not their fault. They’ve been taught the wrong things to ask.

They go into a date with three questions on their mind:

  1. What do you have to offer me?
  2. What do I have to offer you?
  3. Do we want the same thing for the future?

Do you see the problem with those questions?

Those questions frame a date as a transaction.

You’re hoping to get something out of him, and he’s hoping to get something out of you.

If you don’t have enough to offer each other, or if you don’t want the same thing, then the date is over. There’s no point in trying to create a connection.

That perspective dooms dates.

What you want to do instead is frame your date as an opportunity to discover what makes this person tick and find a point of connection.

This approach makes him feel valued for who he is, rather than for what he can offer you.

He sees you as different to other women.

And that creates the perfect setting for attraction to flourish.

So, what are the three questions you want answered by the end of a date?

They are:

  1. Who are you?
  2. What motivates you?
  3. Where do our motivations intersect?

Let’s look at each in turn.

1. Who are you?

Everyone likes to talk about themselves, but the way we talk about ourselves on a first date is highly artificial.

We’re trying to “sell ourselves” to the other person. We’re aware that every single word that comes out of our mouths is being judged.

So, instead of relaxing and speaking openly, we repeat stories that we think will impress our date.

Your goal is to disrupt that pattern. Surprising questions make him let down his guard and reveal more of his true self to you.

Try questions like:

  • If you could pick 3 words to describe yourself, what would they be?
  • What’s your most vivid memory from childhood?
  • What makes you proudest about yourself?

2. What motivates you?

It’s incredibly fun to try and find out what makes someone come alive.

As you talk, notice which subjects make him light up. Is it when he talks about fitness? Is it when he talks about his family? Is it when he talks about the places he’d like to visit?

Then delve in deeper. Find out why those topics mean so much to him.

Try questions like:

  • What’s your favorite part about what you love to do?
  • When did you learn how to do it?
  • That sounds challenging. What drives you to keep going?

As he answers your questions, he feels amazing. He’s sharing what he cares about with you, and you’re actually interested.

At the same time, you’re getting a sense of what matters to him and what drives him. You’re getting a glimpse into his values and his dreams.

3. Where do our motivations intersect?

Now it’s time to use that information to show him that you are compatible in surprising ways.

You may not be able to relate to his hobbies or interests, but chances are you can relate to the feelings that drive him.

You have never ridden a mountain bike in your life, for example, but you understand the thrill of pushing your limits, or the joy of being in nature.

Now it’s time to share your own personal story. Tell him about a time where you pushed your limits or spent time in nature. Show him that you’re driven by similar motivations.

You’re showing him that you “get him” on a deep level.

On the surface, you may not be very much alike. But underneath, you feel much the same.

Try these questions on your next first date, and you’ll immediately see a difference. Your conversation will go deeper. You’ll feel more connected.

And you’ll walk away with a smile on your face, knowing that you’ve completed your mission. That makes your date a success, regardless of what happens next.

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