30 Essential Third Date Questions

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Looking for questions to ask on a third date? Want to know the questions that you MUST ask by the third date (to help with qualifying and understanding compatibility?) Then you’re in the right place! Here’s 30 essential third date questions… Think of this as your guide on what to ask / find out by, by the third date! (Uh huh, after this, you’ll be well equipped!)

What Questions Do You Ask On a Third Date? 

So when it comes to what questions to ask on a third date, you have far more scope than the first or second. You’re no longer strangers. You also know there’s at least a fair amount of interest there. After all:

  1. Not only has this gotten off the dating apps (because yes – ghosting even before the first date, is indeed, a thing!) but you’re now at the proper dating stage…
  2. You’ve also had not just one date, but two…
  3. And now you’re onto the mighty third date. Woohoo! This person wants to spend time with you and are clearly enjoying your company.

And sure – you can’t really blame them. YOU ARE A CATCH! (And don’t you ever doubt it!)

But 60% of dates, don’t actually even get to the second date mark, let alone the third. So this is looking positive. Hopeful even, right?

See, the first date is about getting to know someone, but this isn’t always enough to make a firm judgement on, which is why then comes the second date… 

By the third date, you can begin to feel a little more comfortable and confident.

Yes, it’s still fresh, very-much new and exciting, but this person is starting to become a little more familiar now to you. This creates room for you to step the 3rd date questions up a notch!

So what kind of things should you be asking on a third date?

What to talk about on a third date

Questions To Ask On a Third Date

The questions you should ask on a third date should vary. You still want to keep things light and fun, but you want to now start including some bigger, more qualifying questions. 

What these are (or should be) will be based on who you are and what things are most important to you. This is vitally important to know and understand. There’s not actually a one-size fits all when it comes to essential third date questions as that’s dependent on YOU!

In order to know what your essential third date questions are however, you simply have to break it down to determine your qualifying questions.

To make this easier, we actually have a guide on that:

** How To Determine Your Qualifying Questions When Dating – The Guide **

There’s also pretty standard third date questions that you are most likely going to want to know (or would find it useful to know the answers to.) 

And by this stage, if you also text fairly frequently alongside the dates you’ve already had, it also shouldn’t be too “out there” to ask these.

How Important Are Third Date Questions?

Now third date questions are actually pretty important in the fact that you now have the opportunity to really start exploring this person further.

You want to see how well you click and better gage how well you would (probably) work.

It’s better to “qualify” as much as you can, as early as you can – as this then saves you time (and potential heartache) later down the line.

You don’t want to go into anything blind or waste time on the wrong person.

It is however also important – on the flip side – that you’re not too judgemental or “set in stone” on the things you want or think you need to hear.

It’s still very much early days so bear in mind the fact that:

  1. It can take some people longer to open up than others. This means, you may not get “as much back” from someone as you’d expect, straight away.
  2. It’s not just about the things a person says, but the way they too behave. “Actions speak louder than words”, as they say.
  3. What you may THINK are your most important qualifying questions, may not actually be. So remain open-minded if you’re unsure, and don’t rule someone out too fast, unless you know that this person is definitely not for you (and for a fair, specific reason!)
  4. People can actually change – to a degree, anyway. In the best relationships, you bring out the best in your partner. You also bring out sides they perhaps didn’t know they had. (For instance, if someone who’s never travelled before, dates someone with a passion for traveling, it can inspire them and give them the confidence to get into it too.) You see? So it’s all about balance.
What to ask on a third date

30 Essential Third Date Questions

So let’s get stuck in with these 30 essential third date questions, shall we? 

With each question, I’ll give a brief summary of why exactly it’s an interesting or important one… But remember, ultimately, that’s down for you to decide.

Either way, these questions should also give you ideas and inspiration for how to outline your own third date questions. So really get that mind thinking!

1) How long have you been single? 

If you haven’t already asked this one, it’s an absolute MUST to find out by / on the third date! 

Ask now, ask now. See, you want to know if this person is in the right place, looking for the same things as you.

If they just broke up last week? Well, there’ no way they’ll have had chance to heal, let alone move onto something new, so this is a super important 3rd date question (for sure!)

If they say that they haven’t been single for long, you can then ask…

2) (Casually) Have you fully healed from your last relationship?

This question is particularly relevant if they’ve not been single very long. The last thing you want is to date someone who’s not over their ex.

If they get defensive when you ask this – it could be a sign in itself. So be careful with this one.

Note: There’s actually plenty of ways to lead into this question casually. For example, you could say something like:

“Oh breakups are just the worst, aren’t they? My friends going through one at the moment and I totally feel for her. Did you go through a bad breakup? [Wait for them to answer.] And do you feel like you’ve fully healed from it now?”

 Or, let’s say your date mentions their last relationship, you could then lead into it with:

“Was it a bad breakup then?”  Followed by: “Does it still hurt thinking about it now, a little bit?”

Always be understanding and show that you “get how they feel” (especially if you’ve been in similar situations.) 

It doesn’t necessarily mean that they’re wasting your time and aren’t ready for something new. But the easier they find it to open up to you, the better you will be able to determine this.

You see? So don’t get put off by any of these essential third date questions as they’re not as scary as they may seem!

3) What’s your relationship history like?

Why does this matter? Well, if they’ve never had a long-term relationship – but you have and want one – that’s okay, but only if you can understand why…

Otherwise as we move onto the next question, they could just be saying what you want to hear.

I.E. They say they want something serious, but that’s only because they know you do, and so they’re playing you.

See, in most cases, your third date questions will tie into each other…

4) What are you looking for now?

Are they actively dating and looking to find the right person? And does that align with you?

What are their dating goals? Where are they at? And are they prepared to say, without being worried about what you may think? Can they be open and confident about it?

See, it’s important that you’re on the same page, so questions like this are actually very revealing – especially if you ask them before they have chance to ask you. (They can’t copy what you say then!)

It’s then good for you to share what you want too, as it builds your connection from their side too. When you open up, it may also encourage them to do the same too.

Third Date Questions

Remember: some people have their guards up. They’re afraid of rejection, or of being hurt.

Asking these kind of questions may be daunting both for you and for them, but it really helps you to bond far more, far faster.

Pssst: To avoid heartache or disappointment, I personally, would recommend asking this question as early on as you can. In fact, I’d say it was a question to ask before dating – as there’s no point exploring things romantically if you want completely different things.

5) How do you find dating?

This is a nice, light, easy 3rd date question that’s super interesting as it often reveals their outlook around it too.

Do they enjoy dating? Do they like meeting new people? How nervous do they get? How burnt-out are they with it now?

I mean, do they date a lot? Do they date often? What are their thoughts on dating multiple people at the same time? How long is normal to date before becoming exclusive, in their mind?

When you phrase it all correctly, it naturally flows into a really interesting conversation. You’ll also find out many of the things you’re wondering without even directly having to ask!

6) What are the best and worst things about dating?

Going into a little more detail from our last question – what do they think are the best and worst things about dating today?

What do they wish was different? What things does he / she get frustrated by? Are there any mistakes he / she thinks that people make when dating?

And what does all of this tell you about them as a person?

(This one can actually be especially insightful… Which is why really LISTENING to what someone is sharing, is just as important as asking these third date questions in the first place!)

7) What things have you learnt since dating?

Have they learnt any things about themselves? How did they learn these lessons?

Were these from mistakes they made or through other people? And how open are they about all of this?

Have they learnt more about what they’re looking for, even?

For example, did they think certain things were the most important when dating, but have now realised they’re not the biggest things after all?

This question can prove to be a super interesting conversation and really brings your own relationship on.

8) What are you like in a relationship?

This is one of my favourite third date questions as – again – it’s just so interesting!

See, it’s all great getting to know this person when dating them, but knowing what they think they’re like in a relationship (and what they’re willing to admit!) is very revealing.

And no – you’re not saying you’re necessarily going to get to the relationship stage. It’s just a bit of FUN! But it’s insightful fun. I mean…

  • Would they say they’re an affectionate person? And how does that align with you and what your love language is?
  • Do they like to do lots with their partner? Get that quality time in? Or are they usually out on weekends? Partying?
  • What do they see as having the right balance in a relationship?
  • How easy / difficult do they find it, dealing with conflict? Can they communicate? Can they really listen? And are they able to let things go?
  • How do they tend to act, and what do they think is important when it comes to how to treat a partner?

These will all be very telling things! So if you’re asking this third date question, be sure to expand with other, similar questions that probe them further (without being too intrusive!)

Third Date Questions

9) What kind of person are you looking for?

What do they want in a partner? What’s their “type”? but more than that – what kind of values, morals, characteristics and attitudes are the most important to them?

And how well does that match up with you, and what you’re all about? Could you be the right person for them? Are you compatible with them and what they want?

Always be honest. Never try to MAKE yourself something you’re not, because there will be someone out there who you’re perfect for – just the way that you are! They’ll love you for who you TRULY are – imperfections and all!

On a similar note, another good third date question is…

10) What things would be “deal breakers” for you?

Just like it’s important to find out what they do want in a partner and potential relationship, it’s also important to find out what they definitely don’t want.

This is arguably one of the most important questions to ask on a third date, as it could potentially save you a lot of time and heartache.

See, you can rule yourself out if you’re breaking one of their deal breakers.

You can also potentially rule them out if their deal breakers don’t align with you, or – worse still – conflict with your outlook / beliefs.

If this is the case – always try to understand where they’re coming from first…

Why do they have this deal breaker? And can you see things from their side at all? Only then can you make an accurate decision as to whether this is something still worth pursuing or not.

Essential Third Date Questions

We’re a third the way through our third date questions. So let’s keep them coming…

11) What kind of relationship do you want?

Now you’re going to touch on these conversations the more you get to know each other. But it’s super valuable to understand their relationship vision – even a basic version of it – early on.

This is an especially good 3rd date question, if you’ve already been speaking a lot over text or calls, and you like deeper, more intimate questions.

By touching on topics like this on your third date (if not before), you’re gathering the information you need, based on the things that are important to you, to see how closely the two of you align and whether or not, their desires match your own. I mean:

  • What kind of relationship do they want?
  • How would they want it to be?
  • What do they see as “relationship goals”?
  • What kind of things do they think create a happy, healthy, long lasting relationship? And how would they plan to build this?
  • What things excite them about being in a relationship? Or what things do they value / appreciate the most about them?

12) What are some of the biggest things you’ve learnt from relationships so far?

By the third date, you can start choosing more personal questions to ask a guy, to get to know him better and start to connect further.

Digging deeper – not into the specifics of his past relationships – but what he’s learnt from them, is a really great way to do this.

It enables you to gage his level of maturity, how self aware he is, and how well he’s been able to reflect on his experiences to date.

It’s also a great way to bond, as many past experiences aren’t exclusive to one person and one person alone… They’re shared (especially when it comes to the emotions that come as a result of challenging experiences), and so that creates relatability.

He’ll also be able to see he can open up to you, and you can both listen as well as speak, which furthermore builds trust in your new and (hopefully flourishing) “relationship.”

3rd date questions

13) What are your values and morals?

We’ve touched on morals in many of these third date questions, but haven’t yet mentioned the fact that you can, indeed, directly ask them what theirs are – what’s important to them.

I mean, they may have already volunteered this information when opening up about other things. But every time they open up, that – in turn – provides an opportunity for you to lightly ask.

For example, let’s say they’re talking about the fact that they’d never cheat on someone in a relationship. You could then lead into saying something like:

“I really like. Would you say that living with honesty and integrity are important values for you then?

This is a great way to subtly ask. In fact, you can understand a persons values and morals more, by asking them how they feel about certain things or what they would do in certain situations.

For example: share a story of something that happened to you, that ties in closely with a specific moral or value. Then ask them: “Would you ever do that?!” “What would you have done if you were me?” “Can you imagine how I’d have felt in that situation?!”

So there’s lots of additional ways to go about, finding out a persons values and morals.

14) How important is [variable here] to you?

On a similar note, if there’s things that are important to you (but aren’t values as such), you can directly ask questions to find out if your date is on the same page.

For example, you might like to find out how important: family, animals or money is to them.

Anything and everything can go here. Just make it specific to you and what you want to know, also sharing your thoughts on each topic too!

15) What are your family like then? (Tell me more about them!)

When there’s things that are especially important to you (e.g. family), talking about these in more detail, also then becomes a great third date topic.

Now family is often a big thing. Not only does your family shape how you grew up, but they also continue to influence your life now (for most people anyway.) Which is why family makes a great discussion piece.

I mean, what are their family like? Who are they most similar too? What’s the family dynamics and how is that similar or different to yours?

You may also like to ask: Are your Mom and Dad still together? What kind of relationship do your parents have / did they have, and how has that influenced what you want now too?

16) What’s your relationship like with your parents / family?

Not everyone will want to, or may feel comfortable, talking about their family – so before you ask more questions about them – you may first like to see what their relationship is like with them.

Remember: not everyone is lucky enough to have a good relationship with their family and not everyone is lucky enough to have them around, so always ease into it gently and respect if it’s not a topic that they feel they’re able to talk about with you just yet.

17) What key lessons around love, have you learnt from others?

This could be from friends, parents, grandparents or even sweet, endearing stories from “Joan and Jeffrey down the street.”

They may also be cute, positive, happy lessons, or more serious ones from relationships they’ve watched break down.

But that’s the best thing about third date questions like these – it leaves it completely open for the two of you to decide the tone and “seriousness” of the conversation, whilst keeping it firmly away from the tedious small talk! Talking of which…

what you should know by a third date

18) What does a typical day look like to you?

Now I know what you’re thinking: isn’t that just like the – “what you been up to?” question, you want to try to avoid?! Well, no, actually it’s not.

After all, you’re asking this more generally – to see what their schedule it like and gage how well it fits in with yours. Likewise, you want to see how different / similar the two of you are.

You could also ask questions like:

  • What does your weekend tend to look like? Or…
  • What’s your idea of the perfect weekend?!

19) What things most excite you?!

Now this is where you end up coming up with all of your crazy date ideas, right? As you discover your shared love of adrenaline activities?! (Or something like that, anyway!)

See, you can talk about exciting hobbies, or adventures you can go on… Right the way down to little “weird” or quirky things, you actually think are pretty frickin’ awesome!

Don’t forget to share things yourself to – to encourage the conversation to open up more and more. I mean:

  • Does helping people genuinely excite you?
  • Do you get a buzz from making a meaningful difference?
  • What makes you feel ALIVE?!
  • What things excite you in different areas of your life, and why?

Like I said – you determine the “success” of these third date questions, based on how much you delve into them.

20) What do you like to do in your free time?

This may be seen as a more standard dating app question, but it’s also a good question to ask on (or by) the third date – in person.

After all, you can explore these interests in more detail and better understand their schedule and how closely the two of you align.

Remember: it’s okay to have different interests. It can be a good thing, actually. It’s more about your outlook to life which is the most important thing.

  • Do you both like to keep busy?
  • Do you have different hobbies, but hobbies you throw yourself into?
  • What kind of people are you? And why would / wouldn’t that make you compatible?

21) How much free time do you tend to have?

If you’re asking all of these 3rd date questions (many with ulterior motives!) but are struggling to understand a certain thing – e.g. how much free time does this guy actually have for me?! – then it’s okay to just come straight out with it and ask.

I mean – have these dates been difficult to get? Or has he / she been specifically making time for you? When do they usually have free time? How flexible is their schedule? And how does this compare to you?

After all – moving forward – if things are going to continue to progress, you want to find the best way to make it work…

22) What are your aspirations for the future?

What kind of life do they want to have? And how committed are they to building it? Where do they want to be? And how closely does that align with your vision and goals?

Remember – you should phrase all of these questions in the way that you speak, and in the most casual, informal way.

After all – you don’t want it to come across in a serious interview-style. (It’s not an interrogation!)

But use these to shape your own questions to ask on a third date, and know the way in which you’ll say them, or lead into them, before you go into your date!

what to ask on a 3rd date

23) What are your passions?

This question usually crosses over with the question about what excites them – except with this one, passions are often to do with work, or projects, or things that they feel strongly about.

This makes a great question to ask on a third date as it’s deep – but personal to them.

It usually also turns into a big, interesting discussion, as a person who’s passionate about a certain thing is likely to have a lot to say about it!

If you have specific passions too, now’s the time to bring them up!

After all, passions are a big part of what makes you… YOU. And by the third date stage, you really want to be connecting further and understanding what each other is all about! On that note…

24) What’s your thoughts on [topic here]?

There are endless topics you can select to mull through their mind over – but these must be designed by you.

After all, what things do you want to know about, what will it tell you about this person, and how much does their answer matter to you?

You may ask – for example – what’s your thoughts on politics, religion or specific social issues.

If they don’t have any burning views on certain things – tell them yours and see how they respond; see how well you can talk and bounce off one another; and see how easily your conversation flows!

25) What sort of things are on your bucket list then?!

Not all third date questions have to be serious, or with massively deep intentions. Some questions to ask on a third date should – of course – just be about FUN!

Because hey – maybe this guy wants to go deep sea diving, but you see this as your worst nightmare!

Does it matter? No! Can you have a laugh and a joke over this easily? Absolutely!

So find out:

  • What things have they always wanted to do?
  • What things do they know they HAVE to do at some point in their life?
  • Do they have many bucket list experiences already planned and booked up?
  • Do the two of you have any shared bucket list experiences here?
  • And how much do they think about, and focus on, doing and experiencing new things?!

All of these questions will, in turn, provide a stronger picture of who they are as a person, whilst also proving to be rather entertaining for you too!

26) What was you like growing up?

We’re storming through these questions to ask on (or by) a third date now. So a different 3rd date question to throw in now – is to find out what they were like growing up!

This is not “essential” as such, but it can be super cute and relatable, which helps to build your bond further. (Just what you want!) On a similar note…

27) In what ways have you changed over the years?

What have they learnt? How have they grown? What things helped them to grow? And how do they feel in themselves now, compared to at other times or stages of their life?

This is a pretty big third date question, with lots of exploring to do around it. You’re basically finding out what’s shaped them into them… Which makes it super interesting!

It’s certainly one to ease into though, and make sure you’re both comfortable sharing with each other, to get the most out of this question!

questions to bring you closer to your date

28) Are there any things that you’re still working on?

A great third date question that flows on nicely from the question before – is to look at where they’re currently at, how they currently feel, and if there’s still areas for growth that they’re focusing on.

Remember, there’s no judgements here and this isn’t a therapy session, but instead – it’s about taking an interest in them and their journey…

I mean, perhaps they’re immersing themselves in their fitness right now (something which they shared as a passion of theirs), or perhaps they mentioned that they’re finding dating tough, and so working on their confidence or feeling happier in themselves…

Some of these third date questions can feel daunting, but when you explore the possible answers, you see that they really can be approached and explored, far more casually!

Remember – how they approach personal development / self improvement, can be a big indication of how they approach issues / conflict in a relationship.

It’s also valuable to see how close you can start to become and how well you do actually, open up to each other.

So never be afraid to ask more “out there” questions – especially if you’ve already made it this far to a third date…

People seek connection and so these sort of questions can actually be quite refreshing!

29) When and where do you feel most like yourself?

So maybe formal sit-down dinners are not his / her thing. Perhaps the dating environment as a whole, doesn’t help him / her to completely relax!

For this reason, a great third date question is to look at when and where they feel most like themselves, and are able to be fully themselves.

Does everyone see the true version of them? Do they get shy often? Feel like a shell of themselves in certain environments? Or do they sometimes find themselves putting on an act / show or pretence?

What does their “true self” really look like? What are they like when they’re by themselves? Is it the person that most people see? Why / why not?

See, this is a pretty fascinating question – don’t you think?! This leads me onto our final recommended question to ask on a third date…

30) What’s one thing that most people don’t know about you?

If you’ve reached the third date mark – why not spice it up a bit?! See what they can share with you. See how much they trust you. Or even just have some fun, flirty jokes around this!

It’s still early days, so YES – there’s got to be some “essential” third date questions and slightly more “serious stuff” discussed, but it should all still be good fun in the process, which is why throwing in some unexpected questions works well on a date too!

That’s All For This One

So there we have it – 30 essential third date questions that most people typically ask – plus how to come up with your own essential 3rd date questions (as ultimately, it’s down to you!)

I hope you’ve found this valuable. Wishing you continued success on your dating journey.


Third Date Questions
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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