Here Are 5 Questions to Ask – and a Few NOT to Ask! – on a First Date…

By Adam Armstrong

In response to a blog post I recently wrote on “1st Date Do’s and Don’ts” – a reader named Willie asked me if I’d write a blog post on:

Questions to Ask a Woman on a First Date.

So, here it is…

First Key Point…

Please remember this…

It’s a DATE, not an Interrogation!

Now, I’m not picking on men here. I could quite as easily be saying the same thing to women.

The idea of a first date is NOT to interrogate the person.

If you do this…

If you BOMBARD them with a never-ending list of questions… to see if they ‘measure up’ to your idealistic “Perfect Partner List”…

They’re going to run a mile.

Unless they’re DESPERATE, weak and needy – in which case they may put up with anything (including being “Interrogated”).

Now, I’m guessing you’re not looking for a woman who is desperate, weak or needy! So, from this point onwards, I’ll assume you’re going to be dating high value women (those with some intelligence, confidence and self-esteem).

Questions to Ask a High Value Woman – and Questions NOT to Ask Her…

Of course, there are exceptions to every rule. 

However, in general…

Do Not Ask Questions About ANY of The Following Subjects on a First Date:

• Anything Political
• Anything Religious
• Anything to do with current Social Politics (for instance, if I were single right now, I wouldn’t be bringing up anything to do with BLM on a first date)
• Anything to do with money (people can be easily put off/offended by this)

Those are absolute “no-goes.”

Now, I’m also tempted to say:

• Don’t ask any questions to do with SEX

The obvious exception to this rule is a woman who is overtly sexual and brings up SEX on a first date. If you back out of that conversation, you risk looking like a prude.

However, most women won’t bring up sex. And, in that case, leave questions about sex for AFTER the first date.

In my experience, my dating life used to go like this:

• First date
• 2nd or 3rd date – SEX would happen
• AFTER 2nd or 3rd date, as sex happened again, questions/conversations about sex would happen

Key Point:

The first time you take a woman to bed, you want to make it feel NATURAL for her. So she can tell her friends:

“It just happened”

You can’t question (interrogate) her into bed!

Okay. So those are some key topics of conversation to AVOID on a first date.

Now let’s take a look at:

5 Questions to Ask on a First Date:

1. “How Are You?”

Sounds too simple, right?

But, just imagine it in your head…

You meet the woman at the arranged time and place…

Let’s say, a coffee shop, at 12.30pm, on your lunch break.

You smile, confidently, give her a hug, and say:

“Hey, how are you?”

That’s normal.

That’s natural.

That’s just what people do in conversation.

So yeah, definitely ask how she is! Can’t really go wrong with that.

2. “What Do You Do?”

As the conversation gets going, it’s likely the topic of “What you do” will come up.

Women always want to know what a MAN does for a living.

So, let’s say she asks you what you do…

You tell her…

Then you say:

“How about you? What do you do?”

Again, that’s normal. It’s natural. Nothing weird or controversial there.

3. “How Did That Make You Feel?”

Pay attention.

This one requires some explanation, and it’s very powerful…

Let’s say your date is talking to you about an experience she had that she really enjoyed…

For the sake of argument, let’s say she just got back from 2 weeks Snowboarding in The Alps…

And, she’s telling you about how good the snow was, how great the food was and so on.

At some point in the conversation she’ll hit a “high point” – a point where you can tell she was having a GREAT time…

“I was at the top of this amazing mountain, looking down on the snow. It was just so beautiful” blah blah blah…

When it’s appropriate – perhaps when she’s describing coming down on the mountain on her snowboard, you say:

“Wow. Sounds incredible. How did that make you feel?”

Then she’ll say:

“Oh my God, you know, it was just so perfect. I felt so alive, so invigorated. So free. So adventurous”

Why is this powerful?

Because she’s talking to YOU about all of this. So, subconsciously she’s going to associate all those great feelings to YOU!!!

Think about that for a second.

Time “How did that make you feel?” correctly and it’s an amazing question to ask. It can build attraction, comfort and rapport.

4. “Can You Tell Me More About That?”

Let’s say the woman is talking to you about something that is clearly of real interest to her…

A hobby, interest or sport of some kind.

When she pauses to allow you to speak, be inquisitive… show that you’re really listening to her…

And ask her something more, something deeper, about what she’s talking about.

The question might not be exactly: “Can you tell me more about that?”

But, that is the sentiment.

For instance, say she’s telling you she loves to play the piano. You might say:

“You know, I’ve always loved music, but haven’t ever learned to play an instrument. How long did it take you to get good at playing the piano?”

Sure, that’s a vague, open-ended question.

But, remember…

Women often complain that men are BAD listeners. This question shows you are listening. It shows you are interested.

It invites her to keep talking. 

People LOVE the sound of their own voices (confident people anyway). So, by asking “can you tell me more?” you are building deep rapport while letting her do most of the talking!

5. “What Do You Like to Do for Fun?”

This is a simple question to ask to find out the woman’s hobbies/interests/passions.

It’s also a great way to see how COOL she really is…

If she can’t answer that question…

Or, her answer is only “shopping” or, worse… “drinking”…

You might want to consider RUNNING in the opposite direction. Fast.

On the other hand, if she answers with several different hobbies, and she talks passionately about them all, that’s a great sign.

***

I’ll finish this blog, kind of as I started, by reminding you that it’s a DATE, not an interrogation.

So, use those questions wisely!

If YOU have questions for me, leave them below, in the comments section, and I’ll respond to you asap…

Adam