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Up Your Dating Game With These 53 Flirty Questions To Ask A Guy You Like

Happy, laughing man and woman standing together in front of a blue-painted wall while the woman tries out some flirty questions to ask a guy.

Trying to come up with flirty questions to ask a guy on the spot can be tough. So often, ahead of the date, it’s easy to conjure up tons of questions, only for them to completely disappear from your brain as soon as the first date nerves start to kick in. We’ve all been there.

So, where do you start when it comes to upping your dating game with some of the best flirty questions for him? To help get you started, we’ve put together a list of 53 of our favorite flirty questions to ask a guy you like. From the funny flirty to the romantic flirty, there’s something here for everyone!

What Are Some Flirty Questions to Ask a Guy? 53 of the Best Examples to Choose From

The best flirty questions to ask a guy are all about bringing something different to a date night. They’re a great way to show off your personality and create a more meaningful connection with the person sitting opposite. Below, we’ve laid out 53 of the best flirty questions to ask a guy that you can try!

23 fun and flirty questions to kick things off

To start things off with a bang, these fun and flirty questions to ask your crush are perfect. They’ll bring the laughs, and allow you to chat freely about a wide range of subjects in a chilled, laid-back way.

1. Which high school cliques were you in?

High school stories are usually great to bond over – and very funny.

2. Which series are you binging at the moment?

Who knows? Maybe it’s something spicy that you could watch together…

3. Who’s your celebrity crush?

Hopefully, they’ll say someone who looks just like you!

4. Are there any red flags you watch out for?

This is a great way to establish early on if you’re on the same page, while also sharing funny stories.

5. What’s your worst dating story?

Everybody has at least one ridiculous dating story. Sharing yours and listening to theirs is a great way to have some fun and break the ice. 

6. PDAs: yes or no?

It’s always good to know in advance, just in case.

7. If you won the lottery, how would you spend the first 24 hours?

If you’re looking for things to talk about on a first date, this is a top choice! You can learn a lot about a person by how they’d react to winning the lottery.

8. And what about the first year?

Maybe they’d invest it wisely? Or maybe they’d just blow it all and live like a King!

9. Do you have a go-to karaoke song?

Fingers crossed it’s a classic duet like Islands in the Stream.

10. Which dance moves do you bust out at a party?

And after, you can always ask them for a first-hand demonstration.

11. Can you name the last film you cried at?

Maybe he’ll be as much of a fan of romantic movies as you are!

12. Is there any type of food you could eat every day?

Your follow-up question, of course, should be asking them to cook it for you.

13. Have you ever been backpacking?

Travel stories are always fun to share.

14. Do you play any sports?

This question can lead to great stories and give you a little more context to their personality.

15. Can you describe your perfect vacation?

You can get a real feel for someone’s personality by their answer to this one.

16. Is there any other country you’d like to live in?

Maybe one day you could live there together.

17. If you could have any job in the world, what would it be?

Maybe they’d love to be a lumberjack, or they’re hankering to be a banker.

18. If you were a girl for twenty-four hours, what would you do?

Expect some very silly answers to this one.

19. Is there anything that gives you the ick instantly?

Worth knowing so you can avoid doing it!

20. What are your turn-ons when dating?

This one is sure to turn up the heat.

21. Who was your first-ever crush?

A question that’s silly and flirty in equal measure.

22. What did you think when I first arrived for this date?

This question’s a gamble, but it just might pay off.

23. What would you do if I kissed you right now?

The perfect question to finish a romantic first date and maybe even lead things on further….

Combining flirty and romantic: 11 questions to try 

These next few questions are perfect for when the candle on the table is burning low, and you want to add a little extra amour to the atmosphere.

 24. Love at first sight: do you believe in it?

Hopefully, they started believing in it right after they met you.

25. Can you talk me through your perfect day?

Keep mental notes of this one – maybe you could recreate it for them one day!

26. Do you have a favorite romantic movie?

Let’s see if they can name as many Oscar-winning romance movies as you!

27. What’s something that instantly makes you fall for somebody?

*takes mental notes*

28. When you fall for somebody, do you get butterflies when you see them?

Hopefully, they say yes and experienced it when they saw you.

29. Do you have a favorite romantic story?

It could be how their grandparents met, or it could be their favorite romance novel.

30. Who, in your opinion, is the ideal couple?

Depending on who they say, you’ll have a pretty clear idea of what to expect in a relationship with them.

31. What would your perfect relationship look like?

Then again, this is a more on-the-nose way of finding out what they’ll be like in a relationship.

32. Do you believe that fate is real?

You should be able to crowbar a cheesy response in there somewhere.

33. Which love languages do you prefer?

It doesn’t need to be a deal breaker if your love languages don’t match – but it certainly helps.

34. Do you have any passions?

Seeing somebody get all excited talking about their passions is always a treat.

9 flirty questions to ask a guy over text

Knowing how to flirt over text can feel a bit daunting at first. But, oftentimes, texting can be properly flirtatious. It can be also easier to flirt when you’re not staring into someone’s eyes too, so be confident and have fun with it!

35. How’s your day been?

Okay – it doesn’t sound like the most thrilling question. But it’s always nice to know someone’s thinking of you and cares about your day. This one can always lead to more spicy topics!

36. Can you send me a voice message?

Voice messaging is fast, flirty, and often very funny.

37. Which emoji makes you think of me?

As long as it’s not the poop emoji, you’re all good.

38. Want to hear about the really special dream I had about you last night?

Knowing you were a big part of someone else’s dream can be pretty exhilarating!

39. What things really turn you on? 

Properly one send once you’ve got to know each other a bit better.

40. What about your biggest turn-offs?

Another one to keep a mental note of!

41. Do you think alien life exists?

An interesting text conversation is bound to follow.

42. Do you have any secret talents?

This could be a flirty question or a sensible one depending on what stage your relationship is at.

43. Have you ever been naked in a public place?

Everybody ought to have been naked in public at least once in their life.

Change the pace: 10 deep questions to ask

Sometimes it can be good to change the pace a bit. Below, we’ve laid out some deeper, slightly more subtle flirty questions to ask a guy. These are great for learning more about his personality, allowing you to foster a more meaningful connection.

44. Are you more introverted or extroverted?

If you’re on the same page, great – but then again, opposites attract…

45. Do you have any quotes that influence you?

It’s always good to have a couple of your favorite quotes up your sleeve too.

46. Do you believe in marriage?

Worth knowing early on…

47. Do you know if you want children?

…And even more so!

48. How would you like your life to be in ten years?

Maybe they’d like to be living on an island somewhere, or maybe they’d prefer a penthouse in the big city.

49. Do you believe there’s one perfect person for everybody?

This gives your date a chance to show off their romantic side – or not!

50. What’s your greatest fear?


51. What are your hopes for life when you’re old?

Maybe they have wild career ambitions, or maybe they’re more family focused.

52. What in life do you value the most?

If you’re dating a guy with kids, hopefully, they’ll be the most valuable part of his life.

53. Is there anything that gives you a feeling of purpose?

Because we all need something to drive us.

Be Confident, Be Flirty!

So there you have it! Memorize five of these flirty questions to ask a guy ahead of your date, and you should be able to keep a lively conversation going well into the night. Remember – have fun, relax, and enjoy yourself!

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