57 Best First Date Questions to Get the Conversation Flowing in 2025

First dates can be stiff at times, which is exactly why having good first date questions ready can make all the difference. We’re not talking the generic "What do you do for work?" interrogation that feels more like a job interview, but rather conversation starters that actually take you below the surface. We’ve got a mix of great first date questions to ask a girl or a guy you like that’ll make you look confident and charming without coming off as pushy. If you’re wondering, “What are 20 flirty questions?”— we’ve got you more than covered. Transform that awkward first date energy into chemistry with these great first date questions.

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• Interesting Questions To Ask on a First Date
• Good First Date Questions
• Cool First Date Questions
• Good Questions To Ask on a First Date
• First Date Questions FAQs

Interesting Questions To Ask on a First Date

Even the most confident among us can get tongue-tied when trying to make a good first impression. Add the challenge of figuring out if this person is worth a second date and it can feel even trickier. That's where cool first date questions like these come in. These first date questions will take you beyond the usual chatter so you can dig into who someone really is and figure out if the two of you really click.

1. Has anything surprising or interesting happened today?

2. Who is someone you really look up to?

3. What kinds of trips do you enjoy taking the most?

4. If you could live anywhere in the world for a year, where would it be?

5. What's a book you think everyone should read at least once?

6. What do you love most about your work?

7. Do you have any side projects you're passionate about?

8. What's the most meaningful gift you've ever given someone?

9. How do you usually spend your days?

10. If you didn't have to worry about money, what would you choose to do?

11. What do you do to relax when life gets overwhelming?

12. What's your favorite and least favorite thing about living here?

13. What's something people often get wrong about you?

14. What's something you believed as a kid that you later found out was completely wrong?

15. If you could have dinner with any fictional character, who would you choose and what would you want to ask them?

16. What's the weirdest compliment you've ever received that actually made you feel good?

17. If you had to teach a class on something you're not an expert in, what would it be?

18. What's a small thing that happened recently that made you unreasonably happy?

19. If you could instantly become fluent in any language, which would you pick and what's the first thing you'd want to say?

20. What's something you do that you're pretty sure no one else does quite the same way?

21. If you could swap lives with any animal for a day, what would you choose and why?

22. What's the most useless skill you have that you're secretly proud of?

23. If you had to create a new holiday, what would it celebrate and how would people observe it?

Good First Date Questions

Research shared by Psychology Today has shown that asking questions can strengthen relationships, build trust and even help you uncover the other person’s values. This is especially important for a first date, where first impressions often rely on superficial details rather than who someone really is.

With good first date questions, you can break the ice, spark genuine conversation and create a more meaningful connection. Plus, asking the right first date questions can reveal compatibility early on, so you both know whether there's potential for something deeper.

24. What's something most people think is boring that you find absolutely fascinating?

25. What's the most spontaneous thing you've ever done and do you regret it?

26. What's a skill you wish you could download into your brain instantly?

27. If you had to describe your personality using only movie titles, which would you pick?

28. What's something that always makes you laugh, even when you're in a terrible mood?

29. If you could have a 30-minute conversation with your past self, what age would you visit and what would you talk about?

30. What's the strangest rabbit hole you've ever gone down on the internet?

31. If you had to pick a theme song that plays every time you enter a room, what would it be?

32. If you could relive any day from your life exactly as it happened, which would you choose?

Cool First Date Questions

Once you’ve gone through a few first date ideas and picked something that feels fun and natural, it’s time to bring your A-game, conversation-wise. And nothing says 'I'm genuinely interested in getting to know you' better than asking thoughtful and cool first date questions.

It’s all about exploring the quirky, unexpected corners of someone's mind that reveal their true personality. A bunch of these will clue you into what the other person actually cares about and where they're trying to go in life, so you’re not stuck talking about the weather or how bad traffic was. 

33. What's the most interesting place you've ever stumbled upon by accident?

34. If you could learn any creative skill overnight, what would you choose?

35. What's a conspiracy theory you don't actually believe but find entertaining to think about?

36. If you had to pick a superpower that's completely useless in daily life, what would it be?

37. What's the best piece of advice you've ever ignored, and why?

38. If you could be famous for 15 minutes, what would you want to be known for?

39. What's something you collect without really meaning to?

40. If you had to live in any decade other than this one, which would you choose and why?

41. What's the most ridiculous thing you've ever done to avoid an awkward conversation?

42. If you could have front-row seats to any moment in history, what would you want to witness?

Great First Date Questions

Want to take your first date banter from good to great? We’re not all smooth talkers and sometimes, a good question can go a long way on a first date. These are some of the very best first date questions to ask when all else fails, whether you’re looking for first date questions to ask a guy or a girl. We’ve also included a couple of flirty questions to ask on a first date to keep the conversation playful and maybe even spark a bit of chemistry.

43. What's something you're currently learning that has nothing to do with work or school?

44. If you could solve one problem in the world, big or small, what would it be?

45. What's the most beautiful thing you've seen recently?

46. What's the best decision you've made in the past year?

47. If you had to give a TED talk tomorrow, what would your topic be?

48. If we got stuck in an elevator together, how would you keep us entertained?

49. If you had to pick one age to be forever, what would it be and why?

50. What's the kindest thing someone has ever done for you?

Good Questions To Ask on a First Date

At this point, you might be asking yourself: “What are some fun first date questions I can ask?” Well, we’re turning up the heat with even more flirty questions to ask on a first date, as well as some deeper conversation gems.

Keeping this mental list of good questions to ask on a first date can lead to genuine chemistry and connection, thanks to easier, more free-flowing conversation. We’re not saying you’ll end up in a dramatic meet-cute straight out of a romantic movie, but you will have a far more engaging and memorable time.

51. What's something you believe that goes against popular opinion?

52. What's the most spontaneous adventure you've ever been on?

53. If you could know the absolute truth about one thing, what would you choose?

54. What food could you never get tired of?

55. So, what’s your idea of a perfect date — and am I getting close?

56. If we had to sneak out of here for an adventure, where would you take me?

57. Do you believe in instant chemistry, or do you think it has to build over time?

First Date Questions FAQs

How To Be Playful in Conversation?

A first date is not a place to solve world peace or debate every serious topic under the sun. The goal is to create a fun, relaxed vibe where both of you can feel comfortable being yourselves. One of the easiest ways to be playful in conversation is by mixing lighthearted teasing with genuine curiosity.

For instance, when crafting first date questions to ask a girl, think beyond the standard interview-style inquiries. Instead of asking "What's your favorite movie?" try something like "If you could live inside any movie for a week, which one would you pick and what would be your first move?" This type of question invites imagination and often leads to amusing scenarios you can both explore together.

Playfulness also comes through in your delivery and follow-up responses. If she mentions she's afraid of spiders, you might playfully ask, "On a scale of one to ten, how likely are you to burn down your house if you found a spider in your shower?" This shows you're listening while keeping the mood light and engaging.

And don't be afraid to be a little silly or share quirky observations. Comment on the interesting things around you, create funny hypothetical scenarios or playfully tease in a gentle, good-natured way. Playfulness is about showing your personality, keeping things spontaneous and inviting your date to do the same.

What Should I Ask on My First Date?

One of the best first date questions to ask when you’re just getting to know someone is “What’s something you’re really passionate about?” This gives you insight into their life, what they like and just their personality as a whole. Of course, if you prefer to keep things casual, you can ask something light and fun like “What’s your go-to comfort food?”

Or, you can add a flirty twist to the conversation with a question like ‘What’s the most spontaneous thing you’ve ever done?’ Even playful Would You Rather questions can work wonders for breaking the ice and getting past small talk.

First dates can feel like walking a tightrope. On the one hand, you want to make a good first impression without coming off as rehearsed, but you also want to show interest without sounding like an interviewer. The secret to success here is to ask the right questions. While there is no one perfect formula that’ll give you instant chemistry, having a few good questions to ask on a first date can make things a little smoother.

Whether you lean toward funny questions that get them laughing or deep questions that open the door to vulnerability, these first date questions will help you connect on a real level. They'll also make you stand out as someone worth talking to instead of just another boring date. 

For even more ways to get to know your date, check out other experiences happening on Classpop!