50 Flirty Questions To Ask On Your First Date

First date is so much fun! 

But they can also make us super nervous. All kinds of thoughts rush through our minds: What if the other person doesn’t like us? What if we do something extra silly? 

What if there are lots of awkward silences? 

One of the easiest ways to avoid awkward silences so that the conversation runs smoothly is to ask flirty questions. 

A flirty question must either be fun, light, or a little bit naughty – or even all three simultaneously. 

Either way, it needs to capture their attention and raise their interest levels in you.

In this article, we’ll be going over the top 50 flirty first-date questions you can ask. 

Flirty Questions To Ask On Your First Date

1. So, cards on the table: Are you actually married?

This is a fun question that’s perfect for breaking the ice. Don’t ask it straight away, of course. Maybe ask it when the date seems to be going too well. Ask it in a kind of, “this is going so well that something isn’t right here,” kinda way. 

2. What makes you fall in love with someone?

Ask this to find out what you need to do! 

3. What gets your adrenaline pumping?

Find out what kind of thrill-seeker you’re dealing with. 

4. If I was to check your internet browser history now, what kind of person would I think you are?

I love this flirty question because, while it could easily be taken as too serious in the wrong context, as long as you ask it with a grin and a wink, it should draw out a potentially naughty and mysterious response.

5. Lay your best dad joke on me.

You’re really putting them on the spot with this one. But, hey, everyone has a dad joke!

6. What word can you never pronounce?

I remember being on a date once with a girl who pronounced the “H” in the word “hours.” We laughed about it, and she asked what word I’d pronounced wrong my whole life.

And you know what? It was a great question!

7. Were you excited about our date?

Come on, they had butterflies, right? 

8. Would it bother you if I told you I talk in my sleep?

Test the waters to see how they react to the idea of the two of you sharing a bed. 

9. Fancy sharing your worst photo with me?

Will they actually comply?

Very possibly!

As long as you guys are already in rapport by now, this could be a fantastic way of growing closer on a first date. 

Just make sure not to make too much fun of them when you see the pic! 

10. What would be your superhero name?

And what kind of superpower would they have if they could have one? 

The most extravagant superhero name wins, by the way. The person who loses has to do a forfeit … 

11. What book have you said you read to people … but never actually read?

Everyone has a really famous book they’ve pretended to have read!

Ask this flirty and fun question to find out what secret your first date is hiding.

It would be hilarious if they claimed to have read Harry Potter without reading it, but obviously, we’re all rooting for War and Peace. 

12. If you could get your own personalized number plate, what would it say?

Their answer to this question will actually reveal quite a lot about their personality. 

13. What type of massage do you like best?

This is another flirty question you can ask to test the waters to see how they react. Plus, it puts intimate ideas into their heads and perhaps causes them to picture you giving them a message!

14. Be honest, how many hours a day do you spend on social media?

Who doesn’t spend a lot of time on social media? 

That said, this is both a flirty and serious question. Not only will you see who spends more (or less) time on social media, you might also find out how compatible the two of you really are. 

15. What’s the worst kiss you’ve ever had?

We’ve all had a terrible kissing episode, whether it be the kiss itself or the context. And relating it to a first date can be a whole lot of fun! 

Just remember, though, that if they share theirs, you have to share yours. 

16. How much do you spend a year on shoes? Answer honestly.

Sometimes, what makes a question flirty is the way you ask it.

For instance, this question is probing away at how much a girl spends each year on shopping. It’s a useful question because it shows you how good or bad she is with money and how compatible the two of you are. 

But you’re not just going to be direct and crass by asking, “how much do you spend a year?”

Instead, you’re going to make it a little bit flirty. 

17. What’s the clumsiest thing you’ve ever done?

Hasn’t everyone at some point done something really clumsy?

Find out if you can trust this person with a vase of flowers or not. 

18. What’s the silliest lie you’ve ever told?

We’d all be lying if we said we’d never lied. This question should yield a super funny answer that you can both laugh about before you say to them, “oh my god you are so bad at lying! Never lie again please.”

19. Tell me something about yourself that would surprise me?

Maybe they’re really kinky in the bedroom?

Maybe they’ve got a collection of sex toys?


 20. What’s the grossest thing you did this week?

If they can’t think of anything gross they did this week, how about this month? Or this year? 

Come on, no one’s perfect – they definitely did something gross!

21. Are there any cartoon characters you were sexually attracted to?

Make sure you don’t ask this in a weird way! Timing and context matter, as does your delivery.

Other than that, it’s the kind of question that should get them giggling. 

22. Which celebrity crush do you seriously regret now?

Maybe they crushed on a faded movie star who’s gone really fat now? 

Let’s just hope it wasn’t Santa Claus. 

23. What’s your naughtiest secret?

I mean, the thing with this one is that they probably won’t tell you their naughtiest secret – but whatever they tell you should be pretty damn naughty.

24. Describe yourself in one word

You’ll be really putting them on the spot with this one! 

25. What do you like the best about me

This is a cheeky question, but go for it if the moment feels right!

26. If we went on a second date, where would we go?

The first date would have to be going very well before you asked this one.

27. Do you kiss on a first date or do I need to see you again?

Hey, you may as well ask this if the two of you have been getting along really well. Don’t ask it if you haven’t been getting along (it will sound creepy). 

28. Hey, wanna know a secret

Ooh, this is a great way to pique their interest.

29. What do you like the most about yourself?

Indeed, many people don’t like talking about themselves, but maybe after a few drinks, they’ll loosen up a bit?”

30. What was your first impression of me?

Direct their mind back to when the two of you first talked (or met) and find out what they thought of you.

31. How would you feel if we never saw each other again?

This is another cheekily flirty question, but be warned – they’ll expect you to answer it, too.

32. How would you describe me in three words?

Maybe “flirty” would be one of them?

And what’s a word for “asks tricky questions”!?

33. What turns you on?

Again, this one requires the moment to be just right. Only ask it once the two of you are in rapport. 

34. Do I make you smile?

Surely the answer is “of course”!?

35. What’s the sexiest thing you’ve ever done?

Find out what makes them feel sexy!

36. Are you going to ask me out on a second date or what?

Who said patience is a virtue? Find out how they feel about you right now!

37. Are you a good kisser?

The thing with flirting on a first date is that all modesty goes out of the window. If they’re a good kisser, they will tell you so!

38. If you could take me anyplace right now, where would it be?

… And what would the two of you do there? 😉 

39. What turns you off?

This one might not be super flirty, but it’s still important that you find out what they find unattractive. 

40. Have you ever had sex in public?

When you want to seriously turn up the heat a bit, this is a question to ask. 

41. What’s the naughtiest thing you’ve ever done?

Same as the above question! Ask it when you want to ramp things up a bit. 

42. What’s the craziest thing you’ve ever done?

Find out how adventurous and reckless they are!

43. What is it you like about me so much?

Ask this in the right way (obviously jokingly!), and it won’t sound arrogant at all!

44. What’s the most romantic thing you’ve ever done?

Asking this question is hugely suggestive of your intentions, which itself is essential for flirting. 

45. Have you ever kissed another person of the same sex?

And did they enjoy it? 

And would they try it again? 😉

46. What do you think is my best feature?

Hey, there’s nothing wrong with inviting them to make you feel good!

Don’t repay the compliment, though – just accept what they say and keep the conversation going. 

47. How on earth are you still single? Maybe there’s something you’re not telling me..

This super flirty question encourages them to give you insights into their more mischievous side. 

48. What are you doing for the rest of the night?

Ooooh, this question is a GREAT way to end the first date, IF it’s gone well. 

49. If you could do one thing tonight, what would it be?

Maybe it will involve you? 

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About Mary J. Gibson

Mary J. Gibson, director of DatingXP.co, is a renowned love and relationship coach whose expertise is widely acknowledged across the industry. Her insightful guidance and profound understanding of romantic relationships have earned her features in prestigious publications including Bustle, AskMen, Cosmopolitan, and Elite Daily. Committed to staying ahead of trends, she continually broadens her knowledge by conducting incisive interviews and forging dynamic relationships with emerging dating services, ensuring her advice remains relevant and impactful.