50 Fun Questions To Ask About Dating

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What’s one thing that every single person shares in common? Their relationship status, and the fact that dating is pretty-much inevitable if you’re looking to find love. Looking for questions to ask your date about dating, to see how well you can relate to one another? Then you’ve come to the right place! Here’s 50 fun questions to ask about dating, which specifically focus on exactly that! These are our all-time favourite questions about dating to make conversations FAR more interesting in those all-important early days! So let’s jump straight in, shall we?

How To Ask Questions About Dating

So first comes first, when it comes to questions about dating – when do you ask them and how? 

After all, for some people, asking others more personal questions (about their love life for instance) can feel like a daunting prospect.

You don’t want to come on too strong, or like you’re prying or going to get over-protective right?! You also don’t want to seem like you’re quizzing them. (Not cool!) 

So how do you go about it? Well:

  • Try to ease into questions about dating. Don’t make them the very first questions you ask. Ask some light, entertaining, funny dating questions first!
  • When you do broach the topic, perhaps lead into it by sharing your answer to the question first. Use your story as the conversation starter, then expand by asking them the same question about dating from there.
  • Keep it as a two-way thing throughout! This should be a lighthearted discussion about dating – that’s interesting, fun and relatable. So in between each question, keep it going and flowing by sharing your thoughts / answer on it all too. This only then encourages your date to open up further about dating. (Just what you want!)

Why It’s GOOD To Ask Questions About Dating

Asking questions about dating is a GOOD thing – especially early on.

In fact, some of these questions cross over with the key qualifying questions to ask when dating, because finding out where they’re at, how they feel and what their intentions are when it comes to dating – are all pretty important things!

The good news is, because there are so many different questions to ask about dating, you can mix the “bigger ones” in, more casually.

This way – it comes across as a more general conversation about dating, as opposed to an interrigation!

When you find fun questions to ask about dating, it also makes your conversation different and entertaining. You can relate to each other, open up to each other, and it all becomes rather interesting and insightful… not to mention making you connect on a deeper level, faster!

Has that convinced you to be a little bolder and braver, throwing in some questions about dating on your next date? I hope so. Then let’s move onto the question ideas!

questions to ask about dating

50 Fun Questions To Ask About Dating

So what questions can you ask about dating? What kind of things might you want to know, and what sort of questions are actually pretty interesting to find out about? In no particular order…

Let’s Kick It Off…

1) So how long have you been single? 

2) How do you find single life?

3) What do you think are the best things about being single?

4) What do you think are the worst things about being single?

5) How do you find dating then? Love it? Hate it? Mixed feelings?! 

6) What do you like most about dating?

7) What do you like least about dating? Or what things do you find the most difficult about dating in today’s world? [Here’s Why Dating Today Is So Difficult – Experts Explain!]

8) Do you go on many dates? Would you say you’re quite an active dater? (Just make a point of sharing that there’s nothing wrong with that. In fact, in many cases, it shows they’re probably looking for something serious if they’re putting the time and effort into actively date!)

9) Do you get nervous before going on a date? Or once you’re on that date?

10) What’s your favourite kind of date to go on?

11) How about your least favourite date?! Any that you find mind-numbingly tedious?!

12) Are there any dates you’d LOVE to go on, but haven’t done just yet? Any crazy date ideas you have, even?

13) Do you ever get tired or bored of dating? And what do you do when you do? (Keep trooping on, or take a break from dating?!)

14) Do you have any disastrous dating stories? Where something crazy happened?!

15) What’s been your most embarrassing date? Something that you did on a date that makes you cringe?! (After all, we all make mistakes and have to find out flow when dating! It’s what makes us human!)

Interesting Questions To Ask About Dating

Let’s step it up a notch with some more rather juicy, and insightful questions to ask about dating.

16) What’s been the biggest lesson(s) you’ve learnt since being single?

17) What have your dating experiences taught you so far? (About yourself, your love life, what you’re looking for, etc. Try to get a little deeper with this one! It’s a really interesting question to ask about dating!)

18) What kind of person are you looking for? What things are most important to you? And why?

NOTE: Often we can make mistakes with the kind of person you think you want vs. what kind of person you would actually work well with. This can be another great discussion point!

19) Do you have any deal-breakers when dating? What things do you know WOULDN’T work with you?

20) What kind of relationship do you want to have? Let’s build a bit of a picture in our heads here and see how closely you both align when it comes to your relationship vision!

21) Have you had more positive or negative experiences when dating? And how have they influenced / affected how you go into dating today?

22) What have you been like in a relationship in the past, and – taking everything you’ve learnt now – how would you like to go into a new relationship now? How do you think you would act / be?

23) What do you miss most about being in a relationship? (Which only makes you more excited to find that special person again?!)

24) Are you looking for a relationship now? Where’s your head at? What are your intentions? Just perhaps phrase this a little more casually, and be SLIGHTLY less direct with it! 😉

Questions about dating

Questions About Dating YOU!

Shall we mix it up a little bit? Okay, let’s mix it up a bit! Here’s some (potentially risky!) questions about dating you. See exactly what your date thinks about you… with no holding back!

25) What was your (honest!) opinion of my dating profile?!

26) What was your first impression of me, before you met me?

27) How about your first impression of me once you then first met me?

28) Why did you decide to go on a date with me? What was it that appealed to you, about me?

29) How confident was you that I’d want to go on a date with you too?

30) Was you nervous to ask me on a date? / Was you surprised when I asked you on a date?

31) What’s your favourite thing you’ve learnt about me so far?

32) Is there anything surprising you’ve found out about me so far?

33) What things do you think we have in common? And what things are you liking about how we’re getting on?

34) What’s one thing you still really want to know about me? (Ask me ANYTHING!)

35) What do you think makes me a great date?

36) How do you think I could be a better date? Be honest – I won’t take offence!

37) What’s been your favourite part of this date so far?

38) What’s one thing we could do to make this date even better?! Warning: they may say, have a kiss! [Answered: Should You Kiss On A First Date?]

39) If we went on another date, what would you want to do?

40) Did you expect us to get on in the way that we are?

Questions About Dating THEM!

Let’s spin it around to finish, with some final questions about dating them – to get their opinion, on, well, themselves! There’s also some great questions in here to lead to more “heart to heart” chats, so don’t be shy to ask them when the time is right.

41) What do you think makes you a great date?

42) What do you think are your best “selling points” when it comes to you – as a potential partner?

43) How do you think you could be better when dating? (And what’s stopping you from being this way?!)

44) How do you think you come across when dating? 

45) Do you feel like you’re able to totally be yourself when dating? How so and how not?

46) What kind of people do you think you click most with, and why?

47) What misconceptions do you think people have about you before they get to know you properly?

48) How difficult do you find it to let your guard down and truly let people in when dating? Are you scared of feeling vulnerable, getting hurt, or being rejected at all?

49) What’s one thing you wish people knew when dating you?

50) “Do you have any questions about dating that you’d like to ask me?!”

That’s All For This One

So there we have it – 50 questions to ask about dating, to find out how well you and your date can relate when it comes to your love lives!

Remember, when it comes to asking questions about dating, it should be a two-way conversation, sharing stories, thoughts, feelings and experiences both ways.

Don’t quiz your date! Just use these questions about dating as different and interesting conversation starters.

Have fun. Best of luck!


questions to ask about dating
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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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