50 *Amazing* First Date Questions To Spark A Conversation

So, you’re nervous about what you are going to say! Don’t be, we’ve all been there.

The first dates can be a nerve-wracking experience. After all, they say first impressions last a lifetime. In fact, experts say it only takes about 15 seconds to form an opinion of someone

Your natural conversational skills and the topics you choose to discuss may be the final decider between you getting the cut or getting that yearned-for second date. 

So how do you pick what you will talk about? 

Well, there are always typical age-old questions like: “where do you live, what do you do for a living, and what’s your favorite color.”And, while you will always get around to asking these, they all have one thing in common that you want to avoid like the plague on a first date: 

They are not open-ended questions!

“I live in San Jose, I’m a paralegal, I love the color green…” Boom, that’s it. You’re now back to square one, scrambling to find something else to say. 

You need better first date conversation starters to make things interesting.

Sparking a conversation is not easy but get this: it’s necessary. The first date is THE greatest opportunity for you to not only learn more about that person but also show off your own personality. 

Of course, you don’t want to get into anything heavy like politics, religion, or finances. Those are touchy subjects and they might turn off the person sitting in front of you. 

You want to keep things light, fun, and breezy with the occasional subtle questions that open the door to learning more about them. 

So get ready because we have got the 50 best first-date questions for you to get inspired!

50 Psychology-Based First Date Questions

1. How Do You Feel About Going On This Date With Me?

The possible answers to this question are ENDLESS. “I’m excited to be here, I didn’t know if you were going to ask me out, I’m really glad you said yes, etc…”.  

This is a great conversation starter for first dates. It gives you the opportunity to talk about your initial feelings about this date and to measure their level of excitement. 

2. If You Won The Lottery, What Is The First Thing You Would Do With Your Money? 

This is a chance for you to gauge what their interests are and where their priorities lie. For example, if they say the first thing they would do is pay off their parent’s mortgage, you know that person is family-oriented and is close to their parents. And if they say, they would go to Vegas, well now you know that person likes thrill, excitement, and spontaneity. 

3. What’s Your Favourite Season Of The Year? 

Everyone has a favorite season. If the date is happening during the winter, they might tell you they love snow because they love skiing or snowboarding, and here’s an opportunity to connect over activities you might enjoy doing together. 

4. What did you want to be when you were growing up? 

This question is two-fold. You might get to talk about your respective childhoods and you might get to talk about whether you were able to realize your dreams. 

5. Would you go to space?

Space exploration will soon become something that a lot of people can experience but it’s definitely not for everyone. You’ll get to gauge how adventurous they are. 

6. If you could choose any career right now, what would it be?

The jobs we have may not always be our dream jobs. You might get to discover they have a favorite activity that they would love to turn into a career. Or maybe they already love their career. No matter what the answer, you’ll learn a lot about their dreams and ambitions. 

7. If this was your last day on earth, what would you do?

This is perhaps not one of the best questions to ask on a first date but it is a subtle way of asking what is the most important thing to someone. 

8. What is the one destination you have always wanted to go to?

This will help you determine what this person has already seen, where they have already been, and if they enjoy traveling and seeing new places. 

9. Where do you see yourself in five years?

This is a dreaded question for some people but it might be important to ask. If you want to know if they have any direction for their life, you’re basically asking them to project themselves into the future and you’ll find out what their expectations are. 

10. Do you like kids? 

With this question, you are not really asking them if they want to have kids although they might choose to open up about that right away. The first step is to find out whether they even like being around kids or not. 

11. What qualities do you look for in a partner? 

We all have preferences! Get to talking about what you are both looking for in a potential partner, this might turn into a very interesting conversation!

12. What do you want your life to look like when you retire? 

Are they big planners? Do they live their lives day by day? You won’t know until you ask this type of question. 

13. Are you a morning person or a night owl?

You’re almost sure to get an answer for this! We are all one or the other and we all have reasons for this. By discussing this, you get to find out what might keep them up at night or what motivates them to get an early start to the day. 

14. Are you more of an outdoor or indoor person?

Just like the last question, you are asking your date to tell you more about themselves and to open up about their preferences. If you love the outdoors, you’ll both want to know whether this is something you have in common. 

15. Pick one: go parachuting or bungee jumping and why!

Because first date questions don't have to be boring 😉

17. Do you have a favorite book? 

If your date reads, this will be one question they will love to hear. Ask 'em and they might want to talk about what they liked in that book. If they don’t read, then that’s an extra piece of information for you! 

18. Do you like going on dates?

Not everyone is experienced at dating. Heck, this might even be their first date. Find out if they like going on dates and what they enjoy or dislike about it. If you like this person, you’ll want to have this precious bit of information to be more prepared for the next dates. 

19. Do you remember your first kiss? 

Ha! Well, most of us remember our first kiss. This could turn into an interesting or embarrassing story. Nonetheless, it’s always exciting to start talking about any form of physical intimacy on the first date. 

20. Is there a person that you admire? 

This is a great first-date question. Not only does the person get to tell you if they look up to someone but they might tell you why and how their interests align with that individual. This is great if you're looking to learn more about their aspirations!

21. If your house caught on fire, what is the one thing you would save? 

Well, unless that person actually had their entire life destroyed by a fire (the odds of which are pretty low) this is another question where you get to learn what they value the most. 

22. What’s the craziest dream you’ve ever had?

Almost all of us have had a dream once that was so vivid and so crazy, it marks us for life. But hey, they might not remember a single dream but it’s always something fun to talk about.

23. Do you have any tattoos? If so, what is the meaning? 

They might not have a tattoo but if they do, there is usually an interesting story behind this experience which makes it a great question to ask on a first date.

24. What are you watching on Netflix right now?

Find out whether she likes Netflix and what kind of shows she likes watching. It's a good question to ask on a first date.

25. 5-second rule, yay or nay?

This is just one of those fun questions and it reveals more about someone than you might realize. Are they germaphobes? Do they wash their hands five times before eating? Do they pick up every piece of chicken they see on the floor? 

26. Are you a dog person or a cat person?

This is a pretty straightforward question. You get to find out if they have pets or maybe they don’t even like our favorite furry animals.

27. Tell me about your worst date ever.

A horrible date for one might be an acceptable date for another. This could definitely turn into an interesting story or you might learn about the things they really dislike on a date. 

28. What are your hobbies?

This is a really important question. What do you have in common? Are they really into gaming? Do they spend every night watching Netflix? Do they like hiking or cooking? If you want to have a serious relationship, then it's absolutely important to start talking about shared interests. 

29. What is the most expensive item you purchased?

How a person chooses to spend their money can be very revealing of the types of choices they might make. 

30. What is the best piece of advice you have ever received?

It can be fascinating to find out what someone went through and what lessons they took away from these experiences. Its a good question to ask on a first date because you get to see the depth of a person.

31. Do you like sharing your food at a restaurant? 

Essentially, you want to know if they like sharing with others and how they feel about food. 

32. If you were an alien visiting earth for the first time, what would be amazing to you? 

Shift their perspective and find out if they can see the world as an outsider. It’s all about showing you can see things in a different light. 

33. What is your biggest red flag? 

Get them talking about their biggest no-no. 

34. Who are the most important people in your life?

Maybe it’s a parent, a neighbor, or a teacher who had a big impact on their life.

35. Did you play any sports as a child? 

If they didn’t, that’s ok. But if you are an active person, you might want to ask if they like exercising or doing sports. 

36. What was your most embarrassing moment?

They might not be ready to answer this question. It depends on how well they know you and how judged they might feel. But if they decide to answer it, this question could spark an interesting discussion!

37. What is the first thing you do when you wake up? 

Do they need coffee to function, must they brush their teeth before anything else, or scroll through their Instagram?

38. Are you more of a beach person or a lake person?

When picking a destination for a trip, this just might be the determinant factor. 

39. What do you think people like most about you? 

With this question, you’ll get to see how your date likes to talk about themselves. Are they confident or do they lack humility?

40. Given a chance, would you go back in time or go check out the future? 

You can only pick one! Do they want to correct the past because they have regrets or are they simply curious about the future? This will reveal a lot about their personality especially if they choose to go back.  

41. Do you like working out?

Any kind of movement can be a workout. The thing you want is to find something you can both enjoy doing. It might be hiking, or dancing, or swimming. Physical exercise doesn't have to be a workout in a gym, so everyone should be able to find a physical activity they enjoy.

42. Do you have a New Year’s resolution you were able to keep? 

A lot of our resolutions fail. It would be interesting to find out or share if you were able to stick to something. 

43. What’s Something You Wish You Were Really Good At?

See what skills they already have and what they think would be a good addition.

44. What was your favorite subject in school? 

Everyone will have an answer for this. Science might have been their jam. Maybe you both loved history and hated math. Who knows? Talking about favorite subjects allows you to talk about what draws you in. 

45. Have you got something exciting planned for the weekend? 

This is an interesting question because this might give you insight into what a typical weekend looks like for them. 

46. What type of music are you into?

You might be able to bond over the same taste in music. Ask away and you may even want to talk about concerts or music festivals you have been to.

47. What is your biggest pet peeve? 

We all have one. The goal here is to find out if you’ve got it!

48. Do you think that money buys happiness?

Find out what value they place on money and where they place their happiness.

49. What is your biggest fear?

Find out what makes them feel afraid and be prepared to see their vulnerable side.

50. What Are We Doing After This? 

If your date has been going well, you are going to want to ask them if they want to keep the fun going. This is also an opportunity for your date to let you know if they have the intention to return home after this. Use this question to check in with them to see how they feel!

51. Are You Still Close With Your Childhood Friends?

This is a good way to know more about your first date.

52. What's Your Favorite Holiday Of The Year?

It's an exciting question and if you both love the same holiday then its even better.

53. What is Your Favorite Place That You Can't Get Over?

It subconsciously tells them that you want to travel with them.

54. What's The Most Spontaneous Thing You've Done?

You might hear something you totally didn't expect.

If these sound too generic or plain for your taste then you can try these Flirty questions you can ask on your first date

About Mary J. Gibson

Mary J. Gibson, director of DatingXP.co, is a renowned love and relationship coach whose expertise is widely acknowledged across the industry. Her insightful guidance and profound understanding of romantic relationships have earned her features in prestigious publications including Bustle, AskMen, Cosmopolitan, and Elite Daily. Committed to staying ahead of trends, she continually broadens her knowledge by conducting incisive interviews and forging dynamic relationships with emerging dating services, ensuring her advice remains relevant and impactful.