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The 10 Best Questions To Ask a Guy When Dating

The 10 Best Questions To Ask a Guy When Dating

Questions To Ask a Guy When Dating

So we fired through 100 questions to ask when dating, giving you heaps of ideas for conversation starters. But what are the most important questions to ask a guy when dating? What are the things you should really want / need to know, and how can you use questions to qualify? Well, let’s find out…

What Questions To Ask a Guy And When

When thinking of the most important questions to ask a guy when dating, base it around what’s most important to you. I’m going to give our top 10 questions to ask a guy, but these will vary from person to person. You should also personalise them to make them your own. (But don’t worry, I’ll make all of that super clear and easy!)

When it comes to the “when” you ask part, well – try not to dive STRAIGHT IN with the big boys (of questions!) straight away. Timing is key.

For instance, asking a guy questions that require short or yes or no answers, are fine early on. The ones like how long he’s been single, what he’s looking for, etc. These are actually great early on (before you’ve formed more of a connection) as they’re just inquisitive, they don’t seem to have any intentions behind them as you don’t really know each other at this stage, so they’re actually BETTER to ask earlier than later.

The longer, more personal questions have to be timed correctly however. Some of these questions may actually be pretty deep (or pretty deep by a guys standards) so bear that in mind.

Also bear in mind that some people are more naturally open and conversational than others – so the “when” may depend on the type of person you’re speaking to. Remember, what you’re asking isn’t actually a big deal (especially when you ask in the right way) – you’re just being inquisitive and getting to know this person.

At the end of the day though, you still need to make dating fun. You also have to earn real trust, build up to that openness. So get to know each other first, then start to go deeper.

Should I Ask All Guys The Same Questions?

Pretty much, yes, at some stage or another. However – the key is that the questions should just naturally flow. It’s not an INTERVIEW and there’s no rush for you to find out these things STRAIGHT AWAY. Especially if you want to form a connection and get more open, honest answers.

Having said that, these questions are partially your way of qualifying a person – understanding if they’re on the same page as you, looking for the same things. It just can’t feel forced when doing so, otherwise it won’t work.

I mean for some guys, you’ll be able to TELL some of the answers, you won’t even need to ask. And if you have some deal breakers in there, you’ll know to leave them out and “part ways”. But it’s good to get into the habit of, just generally, being more inquisitive and going beyond surface level when getting to know a person.

These questions are therefore just a starting base to make that easier.

What If I Don’t Like The Answers?

So this is the tricky part isn’t it?! It’s so easy to have a connection with someone, feel that spark, find the attraction is there and then OVERLOOK things that are actually really important to you.

I mean, there’s no such thing as perfection. You will very rarely find someone who genuinely ticks every single box. But if you don’t like the answer, it’s not really what you want – not in terms of how they say it but what the situation is – then you must must must ACCEPT IT.

Whether you choose to still get to know this person, pursue them or turn it into a friendship – it doesn’t actually matters. What matters is that you listen to what they’re saying, this matches up with their actions, you believe it and you base your decision on the truth rather than what you wish was the case!

How Do I Know If They’re Telling The Truth?

How do you know if they’re actually answering you honestly and telling you the truth over what they know (or think) you want them to say? Well, you won’t know. Not always. Or not straight away anyway.

Sometimes you’ll get a gut feeling that they’re blagging – they’re just trying to say all the right things and you don’t believe it because it doesn’t come across as entirely genuine or convincing.

Sometimes you will believe it – and this is a good way to be. Take everything as the truth, or most likely the truth, unless certain things say otherwise. You don’t need to be naturally distrusting or sceptical.

If you feel like you have to question everything and everyone, this is an issue you need to let go of to stop it from tainting your painting experiences or ruining potential chances.

After all, each person deserves a fresh slate. Don’t taint them with your negative views from past experiences.

Just always be AWARE, so that – if there are any signs of inconsistencies or things not matching up – you won’t be so head over heels that you can’t even see them.

Okay So, What Are The Most Important Questions To Ask a Guy When Dating?

So now we’ve got the umm’s and arr’s out the way – what actually are the most important questions to ask a guy when dating? Well, like we said, these questions may vary from person to person depending on what’s most important to you, but here’s a good base to get you started…

Questions To Ask a Guy When Dating

1) How long have you been single?

This is a great question to ask a guy to gage where he’s actually at. You’re not being judgemental. The length of time that he answers doesn’t actually matter – but it is insightful. For instance…

  • He could say he’s ready for a relationship and yet has only been single 2 months, has a habit of jumping from one relationship to another and that then makes sense of his “smitten” behaviour with you when it’s been only a matter of days!
  • On the flip side, maybe he says he’s been single for YEARS, yet he’s still not sure what he’s looking for. That screams a guy who’s just not quite grown up.
  • You may also have someone who – again – has been single for years, only this one’s different. Maybe he said he was focusing on himself, his career, traveling, learning. In this case, you may then be more confident in believing that they are now ready to settle down.

You see? So this question can tell you a lot, particularly when you tie it into other things and get a little more from the answer.

2) What are you looking for?

This question follows nicely on from the first one. You can phrase it in different ways of course, to take away the intensity. So based on how long they’ve said they’ve been single, you could then say something like…

  • That’s awesome! Not quite ready to settle down just yet then?
  • Haha. You sound like an ABSOLUTE PLAYER! 😜 Would take someone mighty special to change your ways then?!
  • That’s cool. So where are you at now? Looking to find the right person, or?

Try to share what you’re looking for too – and not just in one word. Explain where you’re at. This question can also lead into discussions about the kind of person you’re looking for, who you click with, what’s important to you. This leads me onto the next one…

3) What do you think makes a relationship great?

If they’re not sure – run for the hills. Ha! Just joking. But the clearer someone is about what they want and what’s important to them, the better place they’re in.

By asking a guy this question, you get a far better idea of his relationship vision, and the kind of relationship he wants to have (and so could – in theory – potentially have with you.) Some good flowing questions from this one…

  • What are you like in a relationship?
  • What kind of women do you tend to seriously date? Do they all have similar traits?
  • What do you like / miss most about being in a relationship?
  • How about the common challenges there are in relationships? And how do you overcome these?

There’s a lot of relationship-related questions that can branch out from this one. For this however, I’d probably recommend asking a guy these questions either face to face or over the phone…

Make it an open, fun and non-judgmental chat. One that’s interesting more than anything. Also make sure you’re giving your answers as you’re going along too and feeding off the things that he says, adding your own opinions in as well.

By the end of it, you will get a far better idea as to whether you’re on the same page!

4) How have you found dating so far?

This is always a fun one! Try to find out if they genuinely like being single, if they do much dating, what kind of experiences they’ve had, what challenges they face.

Keep it fun and light, whilst still going beyond the surface level of “Oh you know, it is what it is!” Well, no, actually – everyone shares similarities but we all still have different overall experiences, and actually… these experiences shape us!

This is therefore a great question to ask a guy when dating to again, understand where they’re at.

Perhaps you’ll find things you can really relate on. You may also be shocked at some of the things you hear! But I guarantee this question will prove super entertaining and insightful.

5) Are you close with your family?

Moving away from the dating / relationship questions now, it’s time to dig deeper into THEM as a person. This is a great general one that will be important to most people in many ways.

It will show you if family are important to them, tell you a little more about the kind of relationship he has with them. You could also link it onto other questions like…

  • So are you more like your Mum and Dad? And why?
  • Who are you closest with?
  • What was your upbringing like?
  • How has that influenced the way you are today?
  • Family is important to you then – do you want a family or your own some day?
Questions To Ask a Guy When Dating

6) Do you enjoy what you do?

Now finding out what the other person does for work is pretty standard when getting to know a guy, but let’s go one step further by asking him if he actually enjoys it. This will show you:

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  1. If he’s passionate about his work. Something that’s pretty attractive, right?
  2. If he’d be willing to stay in a job he didn’t like, and if so – why? Again, very insightful.
  3. You can also use this to find out how driven he is, how much he values work and success and again, why.
  4. Whats more, you can lead this question onto what goals he has – and whether these are similar to yours or tie into the kind of vision you have for your own life.

This leads me onto one of my next questions to ask a guy when dating…

7) What do you want to do with your life?

So we know what he wants to do in his career, we also know his relationship vision, so why not go the full whammy and find out his life vision… well a touch of it anyway!

  • What kind of lifestyle does he want to have? And how hard is he willing to work for it? How important is it to him?
  • Does he constantly aspire for more, or is he pretty content where he is?
  • Does he want to travel, to see the world? And has he done much of this so far? What places are top on his list?
  • Is he into fitness? Is staying healthy and fit a high priority, and again – why?
  • What are some things he wants to achieve? Some things he’s always wanted to do? Some experiences he HAS to have?

As you can see, you can actually break this question into a number of different questions to then build up an overall picture and see how closely it aligns with what you want.

8) What makes you happy?

Okay so this has got to be one of the most wholesome questions to ask a guy! Whether it’s cuddles with a partner, or football on a Saturday afternoon – there’s going to be a lot of different answers for this one, so again – branch off from it.

Break down specific things. Really try to understand who he is as a person.

  • Does he value friendships and relationships? Is quality time with loved ones a big thing?
  • Does he have any specific hobbies, interests or passions even? How does he keep busy?
  • What does he really enjoy doing? And what are the most important things in his life?

You’ll find out what means the most to him, what his values are, what kind of person he is. For instance, does he have a lot of free time? How does he spend his free time? Is he happy just “chilling” watching tv, or does he have to be doing things, making the most of time?

All of these things will build a bigger picture of him as a person. The key is to not just ask one question and that’s just the answer – probe! But probe and share so it’s a two way thing and he learns equally about you.

9) How would you rate your confidence?

Asking a guy how confident he is a great way to get to know him on a deeper level. See, you want to know how he feels about himself, whether he’s been working on himself, whether there’s things that knocked his confidence and how he re-built it.

The level of confidence that he has and where is came from will tell you a lot. It will also bring the two of you closer when you openly discuss. See, everyone has their insecurities. It’s just how much you allow them to take over.

It’s a great way to bond and lift one another up. You can also get pretty jokey with it too. Confident guys often like women who challenge them – so mix it up a bit!

10) Do you have any burning questions for me?

If you find you’re leading all of the conversations then throw it back to the guy – ask him if there’s anything he wants to know. There should be. Anything… anything at all. And what you end up finding he asks, will actually be rather telling in itself!

Get Clear On What You Want To Know

So there we have it. A great starting point for some of the most important questions to ask a guy when dating. Some of the most insightful!

Your goal should be to find out as much as you can about who this person really is. To do this, you have to take a genuine interest, to really value and care about this person as a human being and want to understand him.

When you do that, not only do you start giving people more of a chance, opening your heart and mind, but you also qualify easier and build stronger bonds and connections.

From this, you’ll actually find you gain some pretty good friendships along the way too – which is great. Dating doesn’t just have to be about finding exactly what you’re looking for. It’s also a great opportunity to connect with new people, which is a truly wonderful thing.

So have fun with it and enjoy the process!


Best Questions To Ask A Guy

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