55+ Flirty First Date Questions | Jaw-Dropping List of 2023

Dating experience | |
Updated On: February 13, 2024
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When you are on a first date with someone, flirting can actually turn out to be more fun than you’d expected. It is a great way to get to know your date a bit better, and indulge in some flirty banter. For the most part, the conversation will flow effortlessly, but at times, truth be told, it will not. And that’s where flirting comes into play. You like this person sitting in front of you, and you want to get to know them. What can get better than a list of flirty first date questions to amp up your date?

We know first dates can be intimidating, and you’re lost about where to begin. But the love guru that we are, we have come to not only guide you out of such sticky situations but to help you leave impressive first impressions as well. So, if you need a little something (or a lot) to get you started, we have compiled a list of 55+ flirty questions for you that you can ask on a first date and make sure to get the sparks flying.

55 Flirty Questions For A First Date

Table of Contents

So you are all set to go on your first date having picked up the most trendy outfit from your closet, and looking your best. But have you thought of what you are going to talk about? What if there is an awkward pin-drop silence throughout? What if the spicy first date questions you prepared end up offending them? You sure don’t want that. Asking some fun flirty questions can help you break the ice on a first date and you can even get to know if you and your date are on the same page. But before we begin, here is a quick pro tip for you: Keep the questions simple, fun, safe, and of course, flirty.

Flirty first date questions

1. What’s the most romantic thing that someone has done for you?

Their idea of ‘romantic’ will tell you how much effort they expect in the relationship while also tipping you off on their past relationships.

2. Do you believe in love at first sight?

Is he the Romeo to your Juliet, or is she the Rose to your Jack? Their belief in love at first sight can really tell you if they are the ‘one’.

3. Can you name three things which always make you smile?

Need we even mention that these three things will now make their way to your to-do list?

4. Are you a texting or a calling kind of a person?

Irrespective of the answer, it will give your date reasons enough to expect the same after the date. And, if everything goes well, you can actually schedule your next one over a call/text, whatever they prefer.

5. How is this date going so far according to you? 

Are they taken by surprise or is it going as expected? Is the date worth repeating or one of those where they would rather lock themselves up in the bathroom than go out to meet their date?

6. What is that one thing that you could talk about forever?

If you see yourself in a long-term relationship with your date, then having an answer to this will keep you in the know of things they are most passionate about. And who knows, this could lead them to show off their oratory skills!

7. What is going on in your mind right now?

Are they nervous about the date or are they thinking of their favorite cartoon character? Are they already imagining their longest relationship ever with you or are they just waiting for the food to be served? We don’t know. We can’t read their minds, but we sure can ask them upfront. Be prepared for a funny answer!

8. Where did you learn to smile that million dollar smile?

Talk about being flirty without going over the top. Compliment them on their smile and see them smile a little more, even as they melt into a mush.

9. Do you think there’s a chance you could fall in love tonight?

Not for the faint-hearted. We’d recommend you to ask this flirty first date question only if ‘you’ are ready to fall in love.

10. Do you know you are driving me crazy already?

Being flirty and coquettish at its best!

11. Have you noticed yet that I am too busy noticing you tonight?

Not only expressing your interest in your date but making sure that they notice it as well.

Related Reading: 100 Questions To Ask Your Boyfriend

12. What’s the secret behind that sparkling look in those eyes?

If only there was a smoother way to drop a compliment!

13. Are you always this much fun to be around?

Throw compliments around like confetti and tell your date you are beginning to love them without saying it.

14. I would like to know a great deal about you. Where would you like to begin?

You know your date wants to take things slowly and steadily if they begin with their celebrity crush. But if they start rattling off their secret fantasy and how many kids they’d like to have, you’ll know where this date is going!

15. Is it too early to ask this: How are you making me feel so amazing already?

You think you both are better together, but what is their take on this? Before you jump to testing your compatibility, see if you two complement each other.

16. What’s your type when it comes to dating?

A relationship can flourish when both of you are either like-minded or when you can mutually respect each others’ views. This seemingly trivial question is in reality a deep flirty question to ask a guy/girl. Find out what dating means for them and if it lines up with your ideas to ensure a happy and lasting relationship.

17. You are making me smile quite a lot tonight, can I return the favor?

See your date grin from ear to ear on hearing this. And if the sparks aren’t flying already, they will now.

18. Do you want to know a secret of mine? And then you can tell me one of yours

When you are enjoying your date and are ready to take things further, you can drop this question to suggest that you are moving on to the next stage — of being each others’ confidant. Gain each others’ trust, confide in each other, and let some skeletons tumble out of the closet, you might be in for a surprise!

19. Are you a ‘party till you drop’ or a ‘Netflix and chill’ kind of a person?

Would they they prefer staying in watching Netflix series for couples or going out to party? Are your preferences similar? Get this matter sorted so that once you start seeing each other, you’d know what to expect over the weekends.

20. Do you want to get out of here and go on a drive?

Feeling like you’re stuck in a rut on your date? Jazz it up a little with this flirty first date question. If it’s a no, then your date is possibly enjoying the evening and wouldn’t want it to spoil the experience. In case it’s a yes, then it’s time to get up and close with them. Either way, it is a win-win for you.

Related Reading: 100 Romantic Questions To Ask Your Girlfriend And Make Her Heart Melt

21.  If a movie was to be made on your life, who would you want to play you?

One of the safest and most fun first date question would be to interrogate them around a hypothetical situation. How they perceive themselves and how they would like to portray themselves will tell you a lot about them.

22. What was your first love like and what did you learn from it? 

Getting to know your date better starts from the matters of heart. Their past relationships and the lessons they’ve learnt will tell you a great deal about them. Are they still clinging to their ex? Are they ready to move on? This probe into the past will keep the conversation going.

23. How would you describe yourself in one word? 

This can introduce you to some hitherto unknown aspects of their nature and personality, giving you a fresh perspective.

24. Are you generally a positive person or do you think the world is doomed?

You might be optimism incarnate, they might be the leader of the pessimism movement. Find out. Similar views can attract, but so can diametrically opposite.

25. Can I click a picture of you so that I can show Santa what I want for Christmas this year?

Or better still wrap them up as a present and carry them home? Well, if only. Sigh!

first date questions
Pick the right questions on a first date

26. Do you like people who ask a lot of questions?

While you might be just trying to engage in some fun and healthy banter with your flirty first date questions, your date might be really annoyed being bombarded with quizzes.

27. What is that primary thing which attracted you to me?

Weave this question in your conversation to find out what they like the most about you and if they are interested in you.

Related Reading: 51 Deep Relationship Questions To Ask For A Better Love Life

28. What are the first five places on your travel bucket list that you’d go with me to? 

Are they a beach bum or a mountain person? Do they like a long, relaxed vacation or an adrenaline fill? A person’s travel bucket-list has more to say than what meets the eye. Also, you’ll find out the odds of you two ending up together.

29. Can you tell me about the best friend you have? 

Knowing about an important person in their life will help you understand them on many levels. If they name their family/sibling/friend, that’s great. If it is an ex, then that might not be a good news for you.

30. Are you a hopeless romantic? Because I definitely am!

Needless to say, it would be a perfect match if the answer is in the affirmative. Exactly what every hopeless romantic dreams of.

31. When was the last time you felt butterflies in your stomach?

Knowing what gives them jitters or makes them nervous is a really intimate piece of information which not many would be aware of. Having an access to such nuggets will indeed bring you closer.

32. Do you have a nickname or am I allowed to call you mine?

Cutesy, cheesy, flirty, and oh-so-adorable, this one takes the cake for being one of the best flirty first date questions.

33. What is your take on the idea of love?

Is it playful and flirtatious, unconditional and selfless, deep and passionate, or lustful love that they believe in? A question that can touch the bottom of their heart, it will help you gauge your compatibility.

34. Did anyone tell you how sexy you are?

No matter what their answer to this is, you’ve made your point!

35. What’s your biggest turn-on?

Ahem, ahem. Now this one is for the dare-devils who are not shy of trying every method to woo their first date. Even if that includes attempts to ask their biggest turn-ons.

36. What are your three favorite things in this entire world? 

Food, music, books, friends/family, art, work/profession, there are so many possible answers to this. But you have to find out which of these is the closest to their heart.

37. You know you are the prettiest person in the room, right?

We know that you know this, but do they know that you know?

Stories about dating

38. Are you feeling adventurous tonight?

Anyone who pops this question at a first date is sure feeling adventurous. But what matters here is how willing they are to go on an adventurous night with you. *wink*

39. What is your favorite thing to do with your date for fun?

Get to know their concept of a fun date only to replicate that later. Or take some inspiration from our list of awesome date ideas to impress them with. Talk about smartly making your way to their heart!

40. What is the most romantic thing you have ever done?

How far can they go in love? Are they willing to take efforts in the relationship? Or are they too full of themselves, expecting you to shower them with all the love and care?

Related Reading: What Does A Third Date Mean For Guys? Third Date Conversation

41. Would you kiss someone on the first date?

This can either bring out a hilarious response or an awkward silence. Either way, popping this question is as crazy and fun as kissing someone on a first date is.

42. Can I plan a crazy next date with you already?

For the ones who aren’t afraid of calling a spade a spade. If you have already planned the next date in your mind, go ahead and ask them straightforwardly if they are up for it.

43. Do you like it when I flirt with you?

Pair it up with a sheepish grin or puppy eyes and you have a heart-winning combo.

44. Will you swipe right on me again?

Basically, it is like asking if they are liking the time spent with you and if they would like to repeat this date.

45. How does a person get to know if you develop a crush on them?

Note down their answers, cross-check after a few dates to see if you can pick up similar cues, and finally figure out if they are interested in you or not — purpose of the question served.

46. What quality do you find the most attractive in a partner?

Is it their looks and personality or the way they talk? Is it their intelligence or their innocence? Things that they find attractive can speak a lot about what they look for in a relationship.

47. What color are my eyes?

If there ever was an award for a spicy first date question, then this one deserves it the most. Get your date to lock eyes with you on the pretext of testing them. Smoothly flirtatious and clever, isn’t it?

48. What are you like when you really let go?

What are they like when they shed their inhibitions? Get an idea of their wild and carefree side which only their close circle knows about.

49. Do you like hugs as much as I do?

Get a hug from your date as bonus to this answer. Are you able to tell if the hug is romantic?

50. Do you think that guys should always make the first move?

Is your date a self-proclaimed ‘modernist’ with age-old beliefs in gender norms that confines expression of love to guys? Or are they the ones who believe in love, irrespective of the gender roles? Find out which category they fit into.

Related Reading: 21 Questions To Ask On A Second Date

51. What is the most daring thing you have done on a first date?

Now this one might turn out to be either downright hilarious and adventurous, or boring and mundane for you. Moreover, you will get to know them better as a person. Are they bold and audacious or cautious and practical? Are they confident and self-assured or self-conscious?

52. Do you have plans this weekend or want to make some?

Do they want to take things up a notch or are they calling it quits already? Put forward this question to gauge their interest in you and who knows, they might already have the next date planned out!

53. What is your take on an ideal relationship? 

This is definitely one of the best deep flirty questions to ask a guy/girl. Their answer will provide you with an understanding of their expectations from the relationship which you can then compare with yours and see if both of you are on the same page. Their perception of ‘ideal’ might turn out to be the biggest relationship deal breaker for you. So, it is better to understand their priorities and preferences to see if they align with yours.

54. What do you consider a perfect date to be?

Is it a romantic candlelight dinner date that they prefer or a casual, more relaxed one? Make a note of what an ideal date is for them so you can plan the next one accordingly. *wink!*

55. How would you react if I tell you that I like you?

A smart question to get them to spill the beans, this one is like proposing to them without actually doing so. Time it well like a trump card and you could be in for a surprise sneak peek into their inner feelings for you.

Flirty first date questions
Make the first date memorable

So, before you go on a date with the next potential suitor, make sure to make a mental note of all these fun, flirty questions that you can actually ask your date and bring a smile on their face in the process. These questions will help you strike just the right kind of conversations you would want on a date instead of making it feel like an interview for the role of your future soulmate.

Key Pointers

  • Asking flirty first date questions can help the conversation going even on dull and awkward first dates
  • Know your date better with questions that can get them to open up about themselves, their feelings, and thoughts
  • Engage in healthy flirtatious banter to keep the sparks flying

So, engage yourself in these flirty conversations and you both can get a clear insight into who you have come on a date with, without feeling the heat. However, the one thing to be kept in mind is no matter how many spicy first date questions you have lined up, do not forego the art of listening. And please, make sure you do not scare away a perfectly good date with your over-inquisitive nature and awkward questions.

This article has been updated in January 2023.


1. What should you not say on a first date?

Serious topics like exes, past relationships, idea of marriage, or asking the person about going back to your place, losing a few pounds, or even ordering their food without asking them etc. are strict no-nos during the first date.

2. How should you end a first date?

You should end the first date on a positive note unless the experience was abusive/toxic/shady. Being polite and gentle is the key. However, it is also advised that you don’t lead your date on by giving them false hopes. It is really unkind to set up a specific time, date, and location for the next date only to cancel it later. Instead, try complimenting them for the time you’ve spent together and tell them politely that you do not believe you two to be compatible.

3. What is the best time for a first date?

As per us, the best time for a first date is midweek-from Tuesday to Thursday, especially during happy hours. Dinner dates may be too heavy for first dates, so you should opt for more ‘casual, chill, and drink’ happy hour dates.

4. Should you hug on the first date?

Mostly, on a first day, the classic handshake is the best option. You can give a ‘hello’ hug if you feel comfortable enough and even hug them goodbye if things went well. However, make sure to have a friendly, side hug first.

5. How soon should you message after a first date?

If your first date already texts you on their way home, it means they really like you. You could wait till the next day to call them up. But don’t wait for more than 2 days.

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