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The Best First Date Questions Dating Experts Recommend For Great Conversations

He's asking her some fun first date questions

Few things are as nerve-racking as going on the first date with someone you like. You’re both a little shy and a little nervous about making a great first impression. So uncomfortable silences feel like a death sentence for any future romance. The cure? Some first date questions that will spark the attraction!

Nothing is quite as wonderful as an amazing first date. Whether you’re getting back out there after a breakup or are tired of your single status and are looking for a relationship, making a connection with someone new can be exhilarating. So you always need to have a mental list of fun things to ask on a first date.

To help you through those awkward getting-to-know-you moments, we’ve compiled a list of questions to ask your date that will not only get the conversation rolling but will spark attraction between you as well.

Read on for our list on what first date questions to ask and why they are so effective at taking your date to the next level.

The Best First Date Questions To Try

Having some interesting questions up your sleeve can help you keep the conversation flowing when you’re on a first date.

Just remember, asking clever questions alone isn’t enough. You also need to listen well to your date’s responses and be prepared to either ask follow-up questions or to share your own point of view on the topic. When you not only listen but offer your own thoughtful responses, your date will know you are truly engaged and interested in what he or she has to say.

Here are 25 great first date questions to get you started:

1. What are you most passionate about?

Showing an interest in your date’s passions never fails to jump-start a conversation. Not only does it give you the opportunity to learn more about your date, but it also gives you a chance to share your own passions. And when two people can share their passions, it never fails to forge a connection between them.

2. What would your ideal weekend look like?

This is a great question for finding out what things they value and activities they enjoy. This query can launch a good back-and-forth dialogue, especially if you share some of the same interests.

3. What is a typical day like for you?

If you want to avoid asking the same boring questions to ask on the first date, this is a clever way to learn about their career without actually asking about it. But you’ll also get the chance to learn what else they do each day. Do they go to the gym? Walk their dog? Volunteer? Binge-watch Netflix? No matter the answer you get to learn about their job and how they spend their time away from work.

4. What would your dream vacation be?

Rather than asking what their last vacation was, this question has the ability to launch a passionate discussion about the future. It’s also a safer question to ask. What if your date isn’t well-traveled or hasn’t been on vacation in years? This helps to avoid those awkward silences that can really kill the vibe.

5. What was the most interesting part of your day today?

Far better than the standard “how was your day” questions, this dating question will force your date into more than an “it was fine” response. It also gives you some insight into what interests them most. Be prepared to relay something interesting from your day as well.

6. What’s your biggest pet peeve?

Maybe you can bond over your shared disdain for people who text at the table or chew with their mouths open. Whatever their pet peeves, knowing them will ensure you don’t commit them!

7. What’s the best advice you’ve ever received?

This might be a question your date will have to think about for a minute — or maybe they’ll be able to answer immediately. Either way, learning what kind of advice they value will help you get to know them better. Be prepared to share the best advice you’ve ever received too!

8. If sleep wasn’t necessary, how would you spend that extra time?

What would your date do with an extra eight hours a day? Share with each other what you’d do with all of that extra time. If the date is going well, you can even make a list of things you’d do together. (This is a great first date question to ask toward the end of your date when you’re both thinking about date No. 2).

9. If you had so much money that you didn’t need to work, what would you do with your time?

This is one of those insightful yet fun things to ask on a first date. It’s a great way to find out what’s important to your date. If you find out you have similar ideas and values, it will definitely deepen your connection.

10. What are the top three things on your bucket list?

This is another excellent way to find out what matters most to your date while also giving you valuable insight into their personality. If you’re vibing, you can even suggest tackling some of your bucket list items together.

11. If you could sit down for a face-to-face chat with anyone, who would it be?

Would it be a family member, a friend they’ve lost, someone famous or maybe a historical figure? There are so many choices. Be prepared to share your own choice as well.

12. What are your top three favorite movies?

Finding out what kind of movies your date enjoys is a great way to bond over favorite genres or individual films. If you haven’t seen the movies your date likes, suggest watching them together some time.

13. Have you read any good books lately?

If your date is a reader, this should launch a lengthy discussion over favorite books. (Hint: Only ask this question if you actually enjoy reading). You can also ask your date for their top recommendation on what you should read next. Then make sure you read the book so you can discuss it on date No. 2.

14. What’s the best gift you’ve ever received?

This question can lead to a lot of shared memories both from childhood and adulthood. You may find yourselves talking about favorite childhood toys, surprise family vacations or thoughtful gifts from past relationships. If your relationship progresses, it also gives you insight into the types of things they appreciate most.

15. What’s the best gift you’ve ever given someone else?

This is a great follow-up question that allows you to reminisce together over times when you’ve done nice things for the people in your lives. This first date question shows you their idea of good gifts to give. It will also reveal part of your date’s personality. Are they creative? Or are they more of a cash in an envelope sort of gift-giver?

16. Who is the most interesting person you’ve ever met?

This is a first date question that will help you learn more about your date and who and what they value most. If they say a parent or grandparent, for instance, you’ll know family is important to them.

17. Are you a planner or do you prefer to be spontaneous?

This is another great question for getting to know your date. Even if you differ on this one, remember, opposites often attract.

18. What’s your all-time favorite meal?

If you’re not already sharing a meal together, sharing your favorite food is a great way to suggest grabbing a bite together.

19. Who is the most important person in your life?

Family member or friend, learning more about the No. 1 person in your date’s life can lead to some really personal and intimate discussions.

20. Would you rather give up dessert or alcohol for a year?

If you want to keep the mood light, would you rather questions are a great way to have a lot of laughs while still learning about each other. Obviously, you don’t want to ask anything too suggestive or weird on a first date, so choose a topic that’s interesting but tame.

21. If you could immediately become fluent in a new language, which one would you choose?

This is one of those fun date questions that invariably leads to a discussion about other countries as well as past and future vacations. Be ready to answer when your date asks you too.

22. What is your favorite type of music? What’s your favorite song?

Few things bring people together like music. Even if you have different tastes, you can try introducing some of your favorite songs to each other.

23. If you won the lottery, what’s the first thing you’d buy?

First date questions that get people dreaming are always great for strengthening the connection between you.

24. Tell me two truths and a lie. (You have to guess the lie.)

This is another super engaging verbal game that is a lot of fun while still helping you to get to know your date. This can go for several rounds back and forth.

25. Have you ever had a life-changing experience?

While not everyone will have an answer for this, those who do will have an amazing story to tell. (Tip: It’s probably best to ask this one only if you have a story of your own).

First Date Questions: More Things to Talk About on a First Date

Need some more inspiration? Whether you want to talk about deep topics with your date or you just want to get to know them a little better, here are some more questions to ask:

26. Are you a morning person or a night owl? What’s your favorite time of the day?

27. Do you believe in New Year’s resolutions?

28. If you could live anywhere in the country, where would it be?

29. What’s your favorite season?

30. What was your favorite cartoon when you were a kid?

31. What’s the most important life lesson your parents taught you that you’d pass on to your own kids?

32. What talents do you have? Do you wish you had any others?

33. If you could invite any five people to a dinner party, who would you choose?

34. If you could have a superpower, what would it be?

35. Would you rather go skydiving or bungee jumping?

36. What three adjectives would you use to describe yourself?

37. What is your favorite way to unwind after a hard day?

38. What’s your guiltiest pleasure?

39. What always makes you laugh?

40. Do you have any unusual hobbies?

41. What’s better, watching the sunrise or the sunset?

42. Which do you prefer, calling or texting?

43. If you could live in another time period, which one would you choose?

44. How do you hope people will remember you one day?

45. What’s your favorite ice cream flavor?

46. What three apps do you use the most on your phone?

47. Have you ever done anything ridiculous to cure your boredom?

48. What topic are you an expert on?

49. What’s worse, showing up super early or being late?

50. If you were going to star in a reality TV show, what would it be about?

First date questions can help break the ice as well as highlight the things you have in common. You can learn so much about each other when you ask the right questions. So the next time you’re wondering what to talk about on a first date, try asking one of these questions!


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