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21 questions you must ask a guy you just started dating

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The early days of dating someone new can be fun and exciting. You’re just getting to know each other, and there’s a lot to find out.

Whilst it’s easy to go with the flow, asking certain questions will help you get to know him on a deeper level, bring you closer together, and make sure that he’s the right guy for you.

Here are 21 essential questions to ask a guy you just started dating.

What to ask a guy you just started dating?

1) What are you looking for?

I know it can seem a bit “heavy” to straight out ask a guy what he wants from you. But it’s vital.

We need to normalize having grown-up conversations about what we want from dating. Because if you want a relationship and he’s only looking for something casual (or vice versa) you’re going to save yourself a lot of hassle by knowing that now.

It’s really common for dating couples to drift along, not communicating about what they really want from each other. Only to discover later down the line that it doesn’t match up.

We’ll happily ask a long list of intimate questions as we get to know someone, yet avoid some of the most important and obvious ones.

Maybe he is ready to settle down and wants kids asap, but you don’t envisage any of that for at least another 10 years. Perhaps he’s just got out of a serious relationship and only wants to date, but you are really ready for something more committed.

Knowing from the start what stage he’s at and whether that lines up with you will save you both wasted time.

Protect yourself from future heartache by being prepared to have the honest conversations from the start.

2) What’s your dream vacation?

Far from frivolous, you’ll actually learn a lot about someone from finding out their ideal vacay.

Not only does the location say a lot, but also the type of activities they might want to do there. Whether they would rather be by the sea or in the mountains, lounge on the beach or explore a city,  peruse galleries or go jet skiing.

Every detail of his dream vacation gives you little insights into the type of person he is. More than that, it also shows you whether your idea of a good time matches up.

I once dated a guy for several years and we took it in turns to choose where we would go.

His choices were always glamorous beach destinations, largely in the Caribbean. Mine were always slightly eclectic — a driving tour of Ireland, Egypt to see archaeological sites, and Iceland to watch the Northern Lights.

In hindsight, this probably reflected that we were quite different people.

It’s not that it matters if you don’t have the same idea of what a dream vacation would be. But what he says will give you interesting clues about his character.

3) What’s the most important thing in your life?

This question is great because it gets to the very heart of who he is.

It’s an opportunity to find out how much he values things like family, friends, work, health, etc.

It’s also a chance to get to know him better and understand what drives him.

If he tells you he loves his job then you know he has a strong sense of purpose in life. If he talks about his family or friends, you know he cares deeply about those around him.

If however, he tells you that his car is the most important thing in his life, well… you may want to rethink.

4) Which superpower would you choose: To fly or to be invisible?

Sure, you want questions to ask a guy to get to know him deeper, but you don’t want it to feel like the Spanish inquisition.

Asking him which superpower he would choose is not only a fun question, but it’s also a sneaky psychological question that will still reveal how he ticks.

Forbes talks about an interesting study asking this very question. Research discovered that people who chose flying as their superpower were far more confident compared to the people who went for invisibility.

Flying relies on being seen and noticed. Whereas with invisibility it’s easier to go unnoticed and sneak around (and potentially observe what other people say about you).

The study also found that people who ultimately feel less powerful or less in control tend to be more inclined to choose invisibility.

It’s not that either is the “wrong” choice, but do you see why this is very revealing about someone’s character?

If nothing else, if you’ve been wondering what are interesting questions to ask a guy, this one has got to be up there.

5) What are you most proud of?

This is another great values-based question. What he chooses shows you what is ultimately most important to him.

It gives you insights into whether he is someone driven more by accomplishments, physical goals or if he values doing things for others above accolades.

For example, he might tell you his proudest moment was getting a promotion, being there for his mom when she was sick, or maybe making it to the base camp of Everest.

Rather than certain things he has done, he could opt for qualities he has cultivated or obstacles he has overcome in life.

Regardless of what it is, you’ll learn a lot about him by knowing what makes him proud.

It’s also a brilliant question as it allows him to show off his best side to you. This is super important as guys want to feel respected.

You see, for guys, it’s all about triggering their inner hero.

I learned about this from the hero instinct. Coined by relationship expert James Bauer, this fascinating concept is about what really drives men in relationships, which is ingrained in their DNA.

And it’s something most women don’t know anything about.

Once triggered, these drivers make men into the heroes of their own lives. They feel better, love harder, and commit stronger when they find someone who knows how to trigger it.

Now, you may be wondering why it’s called “the hero instinct”? Do guys really need to feel like superheroes to commit to a woman?

Not at all. Forget about Marvel. You won’t need to play the damsel in distress or buy your man a cape.

The easiest thing to do is to check out James Bauer’s excellent free video here. He shares some easy tips to get you started, such as sending him a 12 word text that will trigger his hero instinct right away.

Because that’s the beauty of the hero instinct.

It’s only a matter of knowing the right things to say to make him realize that he wants you and only you.

Click here to watch the free video.

6) Who are you closest to?

The way we talk about the special people in our life is a great reflection of character.

Whether he chooses a family member, best friend, or even his dog — it’s not just who he picks that reveals things, it’s how he talks about them.

You’ll see how he responds to intimate relationships. It can be really insightful to watch someone talk about someone they love. How their eyes light up, and their whole demeanor softens.

He’ll probably also end up talking about why he is so close to this particular person, which will prompt him to share more personal stories.

7) What are your top turn-offs and turn-ons in a person?

We all have deal breakers. Now is the time to find out his.

The preferences we each have can range all the way from silly to deep and fascinating.

Knowing what he likes in a person is super revealing about what he is looking for and what he values most about people in general.

It can include physical characteristics, personality traits, and even habits. It’s also really practical info that is going to be useful if you continue to date.

And if you’re on the lookout for flirty questions to ask a guy, this one is perfect. It’s an open question that he can interpret however he wants.

So if you want to turn it into one of those spicy questions to ask on a first date, you can simply ask what his turn-ons are, and see how he responds.

8) What would be a “perfect” date for you?

If you want romantic questions to ask on a first date, then asking about his idea of a perfect date is a good one.

It’s a way to find out what his idea of romance is, without being too cheesy about it. His answer is going to reveal pretty quickly whether you are compatible and your idea of fun matches up.

For example, if he says he’d go to a fancy restaurant with candles and roses, he clearly has a romantic streak.

If he says he’d rather keep things low-key with a pizza and a movie, then it suggests he prefers a more chilled vibe.

Or, on the other hand, if it’s bungy jumping followed by tequila shots, you know he has a bit of a wild side.

This is a fun question to ask because it gives you insight into his tastes and interests.

9) What’s one of the most important life lessons you’ve learned?

One of the serious questions to ask a guy is about important past experiences in his life. Really getting to know someone is about finding out about both the good and the bad.

But of course, you don’t want to turn a date into a total downer. That’s why this is a really great serious question because it still has a positive spin on it.

You are asking about potentially challenging times in life and encouraging him to open up. But you are also allowing him to show how he turned that around, grew from the experience, and came out the other side wiser.

How he answers is going to help you glean his maturity level too.

10) How would your friends describe you?

This question is going to show you his level of self-awareness.

It’s not always easy to describe ourselves. Asking him to step outside of himself and evaluate himself from the perspective of a friend is a good way to get at who he truly is.

It’ll tell you how others perceive him, as well as how he perceives himself.

He may opt for the more complimentary root and say something like “that I’m funny,” or “driven”, but he might also give a more honest assessment like “I’m kind of awkward.”

Either way, it’s going to be revealing.

11) Do you believe in love at first sight?

Another way to steer the conversation down the romance route is to ask whether he believes in love at first sight.

Ok, so science has pretty much dismissed the idea of love at first sight, telling us it’s really an instant attraction. Research has even found that the notion is probably a so-called “positive illusion” that you apply in hindsight months (or years) later once you have fallen in love. You simply tell yourself it was instant.

But regardless, his answer will still be incredibly telling about his views on love. And potentially even whether he’s an old romantic, a realist or a bit of a cynic.

You might even be surprised by his answer.

According to a poll in Harpers Bazaar, more guys believe in love at first sight than women (72 percent of men compared to only 61 percent of women).

A good follow-up question or alternative question might be whether he believes in marriage. This is especially important if it’s something you already know that you want or definitely don’t want.

12) What’s your biggest fear?

This is a deep question to ask someone you’re dating, but he can decide for himself how deep he goes.

It’s not like you are forcing him to start telling you how he lies awake at night worrying he is going to die alone. He can just as easily tell you that he is scared of heights.

But it gives you both the opportunity to open up a little more.

To help you bond and connect, it’s important to make an effort to get to know each other below the surface.

13) What’s the best advice you ever received?

This is another good question to see how his life experiences have made him grow and change over the years.

They could be words of wisdom from parents, teachers, mentors, or even strangers. But these powerful realizations have contributed in shaping him into the man he is today.

If he says something like “my father told me never to trust anyone” then you probably want to run for the hills…and fast.

If he tells you “don’t sweat the small stuff” then you know he’s been through some tough times and knows what it takes to stay focused on the things that matter.

14) What is one thing you really want to do before you die?

Bucket list questions can be great conversation starters.

But more than that, it shows you what excites him, what motivates him, and what his idea of time well-spent looks like.

Whether it’s to move abroad or make a million dollars, this is a perfect chance to let him share his passions with you.

And if he doesn’t have any big bucket list items, it’s ok too. It still says a lot about a person who has more humble drives in life like wanting to raise a family.

15) Do you have any quirky habits?

One of my favorite things about the early stages of dating is all the little quirks that you start to learn about someone.

These are the weird and wonderful things that make us unique.

Of course, there’s a good chance that they also end up being our partner’s “flaws” that drive us nuts when romance turns sour.

But for now, these odd little preferences and rituals tend to feel adorable.

16) If you could change anything about yourself, what would it

You’re going to learn what he considers his flaws to be when you ask him what he’d change about himself.

Not one of us is perfect. Everyone makes mistakes and we all have room to improve.

You’ll see whether he can objectively look at himself in a well-rounded way and see his own imperfections.

Whatever he confesses to you, you’ll know that he’s honest enough to admit when he needs to work on something. This is a really valuable quality to have in any partner.

17) When did you last cry?

This question is a deceptively vulnerable one to answer honestly. This is exactly why it’s such a good indication of how emotionally open he is.

Toxic masculinity is definitely still a thing, and it can feel harder for men to feel comfortable about displaying certain feelings.

It doesn’t really matter when he last cried, but it does matter how he responds to the idea of showing his emotions.

This will give you an idea of how he expresses himself, and how easily he can become emotionally vulnerable.

18) What’s your dream job?

His fantasy job will tell you about his passions, ambitions, goals, and what drives him in life.

It’s also a great chance to show him that you take his interests and aspirations seriously. Which is a big turn-on for a guy.

This relates back to the unique concept I mentioned earlier: the hero instinct.

When a man feels respected, useful, and needed, he’s more likely to be a loving, protective, and committed partner.

And the best part is, triggering his hero instinct can be as simple as knowing the right thing to say over a text.

You can learn exactly what to do by watching this simple and genuine video by James Bauer.

19) If you could wake up tomorrow with one new ability or skill, what would it be?

Without getting too heavy, this question is an interesting conversation starter that can open up to lots of other topics.

It’s less dull than asking what his hobbies and interests are, but you’ll still probably get a good idea of the kinds of things he’s into from his answer

For example, whether he says he’s always wanted to learn how to play guitar, or maybe he wants to learn how to cook like a pro.

Whatever it is, you’ll see if he has a passion for learning or improving skills. It’s a nice way to find out if he’s got a hidden side that he hasn’t shared yet.

20) What are you thankful for?

Questions about gratitude are a brilliant way to get a glimpse into someone’s overall mindset.

Is he aware of his blessings, can he appreciate what he already has in life?

It’s also a good way to get a sense of how much he values relationships and the people around him over things.

Research has found that grateful people tend to be happier and healthier. So regardless of his answer, it’s going to give your conversation a feel-good tone.

21) Who has been the biggest influence on your life?

For good and for bad, the people who surround us have helped shape us into who we are today.

That’s why understanding the most significant people in his life is a bridge to understanding him better.

This question opens the doorway to start chatting about his important relationships. Discovering how he relates to family, friends and other loved ones is a great place to start.

To conclude: What to ask a guy to get to know him better?

By now you should have a better idea of the sort of questions you need to ask a guy you’ve just started dating.

Ultimately there are no right or wrong questions to ask. You should ask him what you are genuinely most curious to know and be guided by what it feels important for you to find out.

The key is getting through to your man in a way that empowers both him and you.

I mentioned the concept of the hero instinct earlier — by appealing directly to his primal instincts you’ll take your relationship further than ever before.

And since this free video reveals exactly how to trigger your man’s hero instinct, you could make this change from as early as today.

With James Bauer’s incredible concept, he’ll see you as the only woman for him. So if you’re ready to take that plunge, be sure to check out the video now.

Here’s a link to his excellent free video again.

Can a relationship coach help you too?

If you want specific advice on your situation, it can be very helpful to speak to a relationship coach.

I know this from personal experience…

A few months ago, I reached out to Relationship Hero when I was going through a tough patch in my relationship. After being lost in my thoughts for so long, they gave me a unique insight into the dynamics of my relationship and how to get it back on track.

If you haven’t heard of Relationship Hero before, it’s a site where highly trained relationship coaches help people through complicated and difficult love situations.

In just a few minutes you can connect with a certified relationship coach and get tailor-made advice for your situation.

I was blown away by how kind, empathetic, and genuinely helpful my coach was.

Click here to get started.

Written by Pearl Nash

Pearl Nash has years of experience writing relationship articles for single females looking for love. After being single for years with no hope of meeting Mr. Right, she finally managed to get married to the love of her life. Now that she’s settled down and happier than she’s ever been in her life, she's passionate about sharing all the wisdom she's learned over the journey.

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