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30 Questions to ask a woman when you run out of things to say

By Herman The German
(Dating Engineer)

Updated September 23, 2024

A man and woman talking about questions to ask a woman.

Dead silence. 

She’s looking at you. But no words are coming out of your mouth. So she walks away, and you won’t ever see her again.

You missed your chance.

Wouldn’t it be great to instantly know what to say when you find yourself in situations like these? 

Or even better, imagine there’s a way to make her do all the talking so you can sit back, relax, and be the great listener all women dream about. 

It’s possible.

But only if you know how to lead the conversation correctly. 

In this article, I’ll share my top 30 questions to ask a woman to create an interesting conversation and become that great listener she’s been waiting for. 

Let’s start with…

Table of Contents

15 Conversation starters to spark an interesting conversation

Remember these words: the first interaction you’ll have with a woman will be the most important one.

If you don’t leave a great first impression on her, then your chances of seeing her again are as slim as beating Einstein in physics. 

To help you create a great first impression, here are 15 fun questions to spark an exciting conversation.

You can use these questions in real-life or via text:

1. If money was no object, what would your dream job be?

2. Would you rather go on a fancy dinner date or play Mario Kart?

3. What do you do to relax and forget about your worries?

4. If you have only one day to live, what would your last meal be and why?

5. What are the three things you couldn’t live without if you were stranded on a deserted island?

6. If you have to give up one of the following forever, which one would it be: books, Netflix, or sex?

7. What’s the worst way a guy has tried to pick you up?

8. If someone were to offer you a million dollars to quit your job right now, would you do it?

9. If your life would have a soundtrack, what would it be?

10. What would your ideal first date be like?

11. If you could be reborn as an animal, which one would you choose and why?

12. Which subject did you hate the most in school and why?

13. Would you rather hit the beach or spend the day at home reading?

14. On a scale of 1 to 10, how much of a spiritual person are you?

15. How did you end up in [insert her job]?

Now, you might be thinking: “Aren’t some of these questions quite boring?” 

Well, it might seem that way, but it can get her to talk or text you about her most important motivations and goals in life…

Which helps you to build trust and a deeper connection.

Just think about it, would you tell a stranger about your life goals and motivations?

So don’t just ask: “What’s your job?”

Unless you want to pass on a great opportunity to create an interesting conversation. 

And since we spend most of our time working and sleeping, she’ll have a lot to say about her work if you ask:

Questions to ask a woman.
Most women spend a considerable part of their day at work. So if you ask her about what made her choose her job, you can get a very long answer.

Get 7 copy & paste messages to start flirty conversations on any dating app

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becomeherman.com copy and paste template

Try them, see her answer, and use the messages any time you want, on any girl you like, forever

15 First date questions to ask a woman to create an exciting date

Epic scenario: You actually managed to get a date with her.

Now what?

First dates can be scary and nerve-wracking:

“What should I wear?”

“Where should I take her?”

“When is the right time to kiss her?”

These are just a few thoughts most men have before a first date. But I found that the most dreading thing about the first date for a man is… that he’s got to talk to his date uninterrupted for at least an hour. 

“What should I talk about so she doesn’t think I’m boring?”

Keeping her entertained for such a long time seems like a big problem.

But just like John Adams, one of the founding fathers of the USA, said:

“Every problem is an opportunity in disguise.”

But how?

Well, here it is…

You just have to talk about her favorite topic in the whole world. 

Do you want to know her all-time favorite topic to talk about? 

Women love to talk about themselves.

Imagine this:

You ask her a question, and she starts talking forever… like doing 90% of the talking while you just lay back, relax, and listen. No more worrying about what to say. And at the end of the conversation, she says: “Wow, this was the best date I’ve been on.” 

That’s probably the dream of every guy out there.

And it’s actually not just a fantasy.

She’ll do most of the talking if you ask her very personal questions. Then all you have to do is to shut up and listen. Trust me, no woman ever complained about a guy being a too-good listener. 

So without further redo, here are 15 deep questions to ask on a first date:

1. What is the most embarrassing moment you had at school?

2. What fictional character would you marry if you could?

3. Who’s your celebrity crush?

4. What was your longest relationship?

5. Where in the world would you like to live if you could live anywhere?

6. What’s your spirit animal?

7. What was your favorite and your worst date ever?

8. What does your perfect day look like?

9. What are you most proud of?

10. What cartoon did you watch the most as a child?

11. Do you have any secret talents?

12. What is your best childhood memory?

13. Have you traveled a lot, and what was your favorite country?

14. Are you closer to your mum or your dad?

15. Do you have a male best friend, and how did you meet him? 

Don’t do this during your first date…

Bonus tip: One of the common first date mistakes is spending your entire date in a coffee place.

Even if you have a great conversation, you’ll eventually get tired from just talking.

So after you spend 30 minutes up to an hour in a coffee place, I suggest you both do something more physical.

It can be as simple as going bowling together. 

The secret to keep her talking

Whenever I show guys my interesting questions, they usually make one fatal mistake.

They start asking her question after question after question. Don’t get me wrong, the questions are great and will get her to open up. But only asking questions, even if you ask one fun question after another, will feel like an interrogation. 

So to make your date not feel like she’s inside a police interview room, you can use a simple trick. 

After she answers your question, tell her how you would have replied to the same question. 

And if she just gave you a one-word reply… answer yourself in a bit more detail. Or share an interesting story related to this question. 

This will subconsciously compel her to invest more and answer your question properly.

Because reciprocity (giving back after receiving something) is a social psychological trigger wired deep in our subconscious. 

Here’s an example to show you what I mean:

A girl on Tinder is helping a man to come up with questions to ask a woman.
If she answers your questions very short, you can get her to answer in more detail by sharing first about yourself.

Your Efficient Dating Advisor

Herman the German

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Guten Tag, I’m Herman The German, original inventor of the Efficient Dating Systems Made in Germany.

I help analytical guys attract & keep almost any woman they want.

Using my background as a Frankfurt-trained financial engineer, I went on a quest to find dating patterns that truly work – my friends asked me to use my cold analytical skills to help them notice recurring patterns in their dating life.

This has been my single obsession since 2012.

Throughout my decade-long research, I was interviewed by German media, curious to know what I’d identified. And I was invited on many occasions to talk on stage as a guest expert – although I prefer the term life-long learner as I keep discovering new principles and techniques in my private practice.

As an introduction to my systems, I’m offering you to try my proven conversation starter template to make almost any woman interested in you, at no cost.

Claim your welcome gift now: www.BecomeHerMan.com/discover

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