17 flirty first date questions that will make them love you

Dating Expert David Hall November 15, 2023 • 10 minutes read

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First dates, what would they be without lots of questions? Weird ones, funny ones, romantic ones, and flirty ones. Asking the right questions will help you get to know your future partner better and make you appear likable to them. ¹

If you are looking to spice up your first date with some fun and flirty questions, then look no more! In this article, we’ve collected a few examples of the flirty kind that will definitely make your date a success.

1. Have you ever been to a nude beach?

A question like this spices things up and gets your date thinking about you in a new light. It’s definitely a flirty question that will get the conversation going!

And don’t think that this question is too daring; most people would probably laugh when hearing it! But don’t ask it in the first ten minutes, of course. Your date should have progressed a bit first so that they don’t think you’re only interested in one thing.

2. What’s your biggest turn-on?

This is definitely a flirty question, yet it’s still respectful. It shows that you’re interested in learning more about what turns them on. Flirting is essential on the first date as it shows interest and builds attraction towards your person of interest. ²

It also opens up the conversation for discussing sexual fantasies and new ideas –which can be very hot. But again, don’t ask this question too early and only if they seem to feel comfortable around you.

3. Which fictional character did you have a crush on as a child?

Probably everybody had a childhood crush on a fictional character, didn’t they? Asking this flirty question is sure to reveal some unexpected answers that can spark an interesting conversation. You could also ask them if they still like that character a lot or if they have no idea why they found them hot.

So the next time you’re out on a first date, don’t forget to ask your partner about their favorite imaginary boyfriend or girlfriend from their youth – it might be quite entertaining!

4. With characters from which genre would you rather fall in love: fantasy or sci-fi characters?

This question is great for finding out more about your date’s taste in love interests. It might also give you some insights into their personality.

If they choose fantasy characters, it might mean that they’re romantic and dreamy. If they pick sci-fi characters, however, it could reveal that they’re more analytical and down-to-earth.

5. Who’s your celebrity crush?

This is another fun and flirty question that’s sure to get the conversation going. It’s also a great way to find out more about your date’s taste in celebrities. Do they like traditional Hollywood heartthrobs or are they more into alternative hotties?

You can also ask them about their celebrity crushes from the past and see how their taste has changed over the years.

6. Would you rather kiss in public or in private?

A question like this is not only a great way to gauge their comfort level with public displays of affection, it is also bound to get your date thinking about kissing you. It’s a minor manipulative trick, but not a bad one!

If they choose public, it means they’re probably comfortable with PDA and are up for some fun. If they choose private, it might mean that they’re a little bit shyer – but that can be quite attractive, too.

Who knows, maybe the two of you will end up kissing tonight?

7. What made you interested in me in the first place?

This is a flirty question that’s also quite bold. It shows that you’re confident and interested in finding out more about why they were attracted to you. It might also give you some insight into what they find attractive in a partner.

This question can be hit or miss, though. Be prepared for a frank answer – and don’t get too offended if they don’t answer the way you hoped for.

8. If I invited you to go sky diving tomorrow, would you join?

A question like this not only shows you how spontaneous and adventurous your date is but also if they’d like to see you again soon. If they say yes, it means they’re probably up for anything – which can be a lot of fun. If they say no, it doesn’t necessarily mean they don’t want to see you again. They might just not be into extreme sports.

Alternatively, you can also add that this is just a hypothetical question if your date seems a bit uncomfortable with the idea of skydiving.

9. Do you like getting compliments?

This is a flirty question that’s also a great way to find out more about what makes your date happy. If they say yes, it means they probably appreciate being complimented and feel good when they receive them. If they say no, it might mean that they’re not used to getting compliments or that they don’t really care about them.

Either way, it’s an interesting question and a good thing to know if the two of you see each other again. And don’t forget: if they said yes, follow up with a great compliment that isn’t too superficial!

10. What’s the best pick-up line anyone has ever used on you?

This question is bound to get a few laughs and maybe a great story, too! And it might also give you some insights into what your date finds attractive. Do they like cheesy lines, or are they more into flirty banter?

It’s also a great way to test out your own pick-up lines on them to see how well they work. And don’t forget to ask if the other person succeeded with their pick-up line!

11. What’s your sexy spirit animal?

This is a fun and flirty question that’s sure to get the conversation going. It’s also a great way to find out more about their taste in animals.

By their answer, you can also tell what kind of person you’re dating – are they fierce and confident, or do they prefer a cuddlier or even fun approach?

Will their sexy spirit animal be a fiery fox or a cuddly manatee? Just make sure you have a great answer to this question as well!

12. What’s your secret fantasy?

This is a great question for many reasons! First of all, it’s a fun and flirty question that will definitely get the conversation going.

They can answer it however they like. Their answer can be naughty, but also very wholesome! It’s also a great way to find out if your date has any secret fantasies they want to explore or share – and who knows, maybe you’ll be the one they do it with!

But depending on who they are, they can also answer in a way like: “I always wanted to be a baker.” So don’t expect them to be naughty or anything if they aren’t into that! Just go with whatever answer they give you.

13. What’s your favorite thing to do when you’re alone?

This question is a great way to find out more about what they like in their downtime. Are they into reading or traveling? Do they love catching up with friends and family, or are they more of an introvert at heart?

You’ll also get a sense of how they like to spend their free time and if they’re the kind of person who likes to be always on the go or if they prefer a more relaxed lifestyle.

14. Did you at any point in life like the idea of having a sugar daddy or sugar momma?

Not every person would answer this question truthfully, but if they do, it can be a great way to find out more about their preferences. Do they like the idea of dating someone older whose wealth allows them to indulge in all sorts of luxuries? Or maybe they’re more into the sugar baby role – getting spoiled by an older, sugar daddy-like figure and living a life of luxury.

But the best part of this question is the past tense: they can tell you the truth without giving away if they would still be down for something like that.

Just keep an open mind when you ask this question and see what kind of answer you get. Whatever their answer is, just go with it and enjoy learning more about your date!

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

Attention: this question has the potential to ruin your date and make it very uncomfortable. Only ask this question if you’re sure that your date is flirting with you and if you think they would be down for a little bit of fun.

But if they are, then this can be a great way to find out! And if they answer that they would love it, you could let them dangle a little bit and see if they make the first move. Building up anticipation is a great way to make it extra hot!

16. What’s your favorite thing about your body?

This is a great question for two reasons. First, it’s a fun and flirty way to find out more about their confidence and what they like about themselves.

Second, it’s a great way to compliment them! By asking this question, you’re telling them that you find them attractive and that you appreciate their body.

Whatever their answer is, just go with it and add your own compliment to make them feel good about themselves.

17. Are you free on Friday? (or any other day)

This is a great final question to end on! Not only does it check in about whether or not your date is available to go out with you again, but it’s also a nice and flirty way to signal that you’re interested in hanging out again and enjoyed your first date.

If they are free on the night you suggest, then hopefully they’ll say yes! And if they say no, you can always try for another night or ask if they want to do something during the day.

But regardless of their answer, just remember to be respectful and understanding – after all, they might have other plans or commitments that they can’t change!

We hope you enjoyed our article on flirty first date questions. Good luck on your next date, and remember to always be yourself!

If you need even more help, you should check out these links:

How to flirt: The ultimate booklist for men and women

Flirting is an essential part of any relationship. It's the way to test the waters, to see if there's potential for something more. If you're looking for some guidance on how to flirt like a pro, look no further than this list of books. From books that teach you the basics of body language to books that delve into the psychology of flirting, these are the best resources out there.

Huang, K., Yeomans, M., Brooks, A. W., Minson, J., & Gino, F. (2017). It doesn’t hurt to ask: Question-asking increases liking. Journal of personality and social psychology, 113(3), 430–452. ↩︎
Feinberg, S. L. (1996, May 1). Teasing: Innocent Fun or Sadistic Malice? (First Edition). New Horizon Press. ↩︎

Dating Expert

David Hall

David Hall is a self-taught dating expert who works as a freelance writer to help people improve their love lives. He has always been interested in dating, physical attraction, and …

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