53 Flirty Questions To Assert A Guy You Like In 2023

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?

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 roman

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 romantic 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 romantic novel.


About the Author

A prolific love author who specializes in creating love stories often focused on the romantic connections between people which readers can identify with.