The 10 Most Important Questions To Ask A Man On A First Date

Let’s be honest here: First dates are always a little bit nerve-wracking!

You’re probably nervous about what he’ll think about you, or how things will go…

What’s more, you’re probably wondering what he’s really like as a person, and hoping things will go smoothly…

Wouldn’t it be nice if you could just let go of all these thoughts, relax and enjoy your time?

It’s a tricky subject, but we can help you out!

As dating and relationship experts, we’ve helped thousands of women around the world become more magnetic, charismatic, and attractive.

And today, we want to help you tackle one of the biggest challenges in dating: The first date!

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The 10 Most Important Questions To Ask A Man On A First Date

When you go on a first date, you have a few goals:

You want him to like you, to leave a great impression on him, and you want to enjoy your time too.

But you also want to find out about him as a person, and whether he’s a man who will treat you with the love and respect that you deserve.

If you’re wondering how exactly to do all this, you’re in luck!

In this article, our team will walk you through the 10 most important questions you should ask a guy on a first date.

These questions are designed to generate meaningful and interesting conversations, making him open up his heart to you.

What’s more, they will also make sure your date goes smoothly, and lay down the foundations for a deep emotional connection.

Later in this article, you’ll also have an opportunity to grab a free copy of our complete guide to a perfect first date.

So if you’re wondering what exactly you should say or do on your upcoming first date, pay attention. These 10 questions will change how your dates go forever!

1. What Does Your Ideal Relationship Look Like?

There’s nothing more important in a relationship than the foundation you’re building it on.

This means you want to make sure that you both want the same things in life, and in your relationship.

If you don’t get this part right, it can spell disaster for a relationship later on. So it’s a great idea to sort it out right from the start.

What’s more, this question will clear up a lot of uncertainty and doubt.

When it comes to the beginning of a relationship with a guy, it’s quite common for girls to wonder: “What is he looking for?” and “Is he just a player?”

Bringing this question up will clear things up for both of you, and allow you to feel more at ease and open for the rest of the date.

This also makes it a lot easier to form a genuine emotional bond with each other!

2. How Do You Usually Spend Your Weekends?

This might seem like a weird question at first. But here’s why it works:

If he spends his weekends sitting in bed reading, while you spend your weekends out at the club partying with friends, he might not be the ideal partner for you…

But if you find that you spend your weekends in similar ways, the conversation will flow very easily.

If you and your date both enjoy reading, for example, you’ll go on to talk about your favorite books.

Or if you’re both outgoing and social types, you might talk about your favorite pubs and clubs.

These sorts of conversations will really bring you two together, because it gives you a chance to bond over common interests.

And not only that, you will pick up some deep insights into his personality and values, and draw some conclusions as to whether he’s a man who will treat you well.

Because let’s be honest: You don’t want to be in a relationship with someone who you can’t relate to at all, right?

(To learn more about conversations that bring people together quickly, check out our guide to a perfect first date here!)

3. What Was The Worst Date You’ve Ever Been On?

Here’s a cheeky question to get your conversation flowing!

Not only does it keep things light, but it also gives you a chance to learn more about him as a person.

At first, you might feel like this is an awkward topic to bring up…

But in reality, this question brings a fun and playful vibe to your date, and builds a sense of trust and closeness between you too.

And in a way, talking about a bad date in the past also makes your date look good in comparison!

The important thing is to keep things light and comfortable. The last thing you want to do is make this question sound too serious.

Depending on how he reacts, you’ll be able to see whether he’s emotionally mature and open about these sorts of things, or someone who’s more shy and reserved.

There’s no right or wrong answer here: It just gives you a chance to see if he’s compatible with you!

4. What’s The Most Embarrassing Thing That’s Ever Happened to You?

When it comes to first dates, it’s only natural that we try to present the best version of ourselves…

But sometimes, this can actually keep us stuck in our heads, and closed up from each other.

So here is a great question to break down these walls, and allow ourselves to open up to each other.

It will also help you determine whether he is comfortable with revealing his more vulnerable side.

And most women agree: It’s important for a man to be able to laugh at himself once in a while and not take himself too seriously.

What’s more, people feel closer to each other when they share personal stories, especially the awkward and embarrassing ones.

And once he sees that you’re someone who he can express himself freely to, he will start to form a strong emotional connection with you.

(Check out our guide to a perfect first date to learn the “shortcut” to forming a strong emotional bond with any man!)

5. What Were You Like Growing Up?

Like it or not, our lives and personalities are all shaped by our childhood.

So if you want to get to know a man on a deep level, start with his upbringing.

A great start would be what he wanted to be when he grew up, or what were his interests and talents.

Because chances are, these are the same things that are important to him right now.

This will give you a really good idea about what his values and dreams are, and what really drives him in life.

Talking about his own childhood will also make him feel great, because men love looking back on the “good old days”.

That being said, not everyone has had a pleasant childhood.

So if you detect any tension or awkwardness as you bring up the question, it’s best to drop the topic and move on to something else.

6. Who Are The Most Special People To You?

There’s no better way to get to know a man on a personal level than to understand the people nearest and dearest to him.

This question will give you a chance to find out who he values the most in his life, and what sort of people he surrounds himself with.

It also gives you a clue as to whether he treats the people around him with love and respect, which is an important part of who he is as a person.

After all, how he speaks about the people who are closest to him will be a reflection of how he treats you in your potential relationship!

Overall, this is a great question to get him to start opening up to you about the deeper aspects of his life and personality without making things uncomfortable or awkward.

(For more ideas on how to make him open up his heart to you on your first date, click here to check out our complete first date guide!)

7. Who Are You Closest With In Your Family?

Just like his childhood, his family members and his relationship with them will have a massive impact on who he is as a person.

These sorts of topics may seem common or basic, but what you get back can be very insightful.

The key is not to focus on his answers, but on how he delivers them.

For example, a common reply to this question may be siblings.

But some men might light up and spontaneously start telling you stories about them growing up, while others will just give a cold answer without elaborating.

It’s the way that they talk about these close family members that matters the most. If he talks about them with passion and excitement, you’ll know that he has a great relationship with them.

And guys who grew up in loving families will usually be caring and thoughtful to their lovers too.

Once again, it’s important to bear in mind that some people have had rougher upbringings than others.

If you feel like this is the case, it’s best to just let this topic go and chat about something else instead.

8. What’s The Craziest Thing You’ve Ever Done For A Girl?

At some point, you’ve probably done some crazy things in the name of love…

And no matter how much he doesn’t want to admit it, chances are he’s got a few of these stories himself!

So if you want to find out about him and melt his heart at the same time, here’s a great question to ask him.

On one level, you can tease him and put him on the spot. It brings a flirty, cheeky vibe to your conversation.

But more importantly, it encourages him to open up about his vulnerable, embarrassing moments.

This question can also melt his heart and flood his body with the same feelings of romance he felt for this girl…

Only this time, these feelings will be directed to you!

(Check out our first date guide to learn the quickest and easiest ways of making him feel this way about you!)

9. What Is The One Thing About Yourself That You’re Most Proud Of?

This is a question that will challenge a man.

We all know that pride is very important to men, and they love bragging about their accomplishments, especially among male friends…

But when you ask him to name the one thing about himself that he’s most proud of, it puts him on the spot.

Chances are, he hasn’t really thought about this. He might have a lot of achievements and characteristics about him that he’s proud of, but it’s not easy to name the one that matters the most to him.

What’s more, this question makes it clear to him that you are the “prize”, and he is the one who has to try to win you over.

It forces him to come up with an answer that is impressive but not too arrogant.

And depending on what he says (and the way he says it), you will be able to tell a lot more about his personality and character.

10. How Do You See Yourself As A Person?

Just like the previous question, this one puts your date on the spot and gets him to talk about himself.

It puts him in a position where he can’t sound too boastful, but also has to win you over.

You see, we all have a vision of our “ideal selves”.

And the interesting thing about this question is that guys will usually reply with this vision of themselves.

This answer will give you some insight into his self-esteem confidence, as well as his dreams and aspirations for the future.

It also lets him know that you are interested in getting to know the big picture of who he is as a person, rather than just his surface qualities or what he does for work.

And by sharing these deep aspects about himself, he will also feel drawn to you too!

The Proven Step-By-Step Formula For A Perfect First Date

As women, one of the biggest anxieties for us when it comes to first dates is this:

“I wonder if he will like me…”

This is especially true if it’s with a guy you’re very attracted to! And it’s perfectly normal to get these thoughts.

As international dating and relationship coaches, this is a question that we get time after time again.

And we’ve helped hundreds of women around the world overcome these worries.

How? It’s quite simple.

We give them a step-by-step blueprint for a perfect first date.

Because once you know with confidence that the date will go smoothly, and that his heart will be absolutely captivated by you within the first few minutes, you won’t have a reason to worry at all!

We want to help you do the same. So to get you started, we’ve prepared a handy guide on the key secrets for a perfect first date. And today, it’s yours for free: