49+ First Date Questions to Help KILL Long Silences


Silas & Grace

A black and white photo probably taken back in the 1940s or 1950s. The man and woman are both sitting at a cafe table on a date and they look like they're having a great time.

Finding the right first date questions is kind of the worst.

I mean, meeting up with a person for the first time honestly isn’t that fun. It can be, but then you have to overcome that overwhelming thought, “What if this gets weird?”

And I feel like this gets even worse when it comes to first dates. You want to make a good impression, and you really don’t want there to be long silences.

But that’s where knowing good first date questions comes in handy. You have to know the right ones, and sadly, there are so many bad ideas online that don’t help the situation.

I get so TIRED of hearing conversation starter ideas that make me think:

  • “That’s so weird, who asks that?”
  • “I would have to be a middle schooler to start a conversation like that.”
  • “If I asked that questions, I’m pretty sure they’d walk out, and immediately block me on all social media accounts.”

So, I’m here with an actually useful list of questions for your first date, to help ease your anxiety.

So let’s get rid of that anxiety. 👍

Related: 10 Conversation Topics That Are Actually Useful

A Helpful List of First Date Conversation Starters

A girl and guy being affectionate with each other. The girl is asking him a first date question.
Photo by Jonathan Leppan via Unsplash – Edited on Canva

These ideas for first date questions are here to help you:

  1. Level up in your life: I’m all about helping you to level up in almost every part of your life. And making sure your first date goes amazing, is one of them. You deserve to actually find the right person, and be happy doing it. Not be stressed out.
  2. Have follow up questions and extra ideas: A lot of these questions have follow up questions + tips to make it work for you. I don’t wanna leave you hanging with just a simple list of questions.

So let’s get started!

Related: 279 Love Quotes That Are [Seriously] Share-Worthy

Questions for the Beginning of the Date

1. Hey, how has your day been? Anything interesting happen?

I feel like this is a very easy going way to start a conversation, if you’ve both just met up.

You’re making it about them, which is great, and giving them the opportunity to relax, and get rid of any nerves they might have.

Also, if something interesting did happen, you can ask them more on the topic:

  • What did they do?
  • What did they think?
  • How did they react?

There are so many places to take this!

More Good Reading: 19 Ways to Make Friends as an Adult (And How to Keep Them)


2. So tell me, what are you looking for right now?

I’m not saying you have to ask this right away, but I feel that it’s one of the most important questions on a first date.

It could be that you’re both not right for each other, and it would be good to know that early on. Then you’re not wasting each other’s time.

3. What made you take an interest in my profile?

Make sure to let them know that they’re not pressured to give a specific answer, you’re just genuinely curious!

Was it something about your appearance, interests, job, and/or a hobby?

It’s a great way to get a little bit of insight into the other person.

First Date Questions for Dreams & Passions

A breakfast date, where a couple can ask first date questions.

4. Are you working towards any big or small goals right now?

Whether it’s a project, or even a financial goal, this is a great conversation starter on a first date.

You’re getting to know what drives them, what kind of ambitions and dreams they have, and then you can of course follow it up with more questions.

This leads you both away from awkward silences, but also helps you know if you’re compatible.

And if you are, then it’s an exciting way to get to know how this person works! 😊

More Good Reading: 127 Positive Affirmations You Can Use Every Day

5. What’s Your Dream Job?

I think this is a great first date question to ask, if they’re in a spot in their lives where they’d like to move away from their current job. It gets them thinking, and shows that you’re actually interested in what they want with their future.

Or if they’re happy with their job, they probably still have a dream job they might prefer. So in the end, it’s just a fun question to ask, and it helps you to get to know them better. 👍 

6. Is there anything you’re really passionate about?

Follow up question: Could you tell me more about {insert passion}?

Almost everyone has something they’re really passionate about, so you can’t go wrong with this question.

Take an interest in what they’re passionate about, see if it interests you, and get to know them better. See what makes them excited and happy in life. See what they love!

It’s a great question that helps you make the most out of the first date.

Related: 39+ Love Poems That Are [Undeniably] Share-Worthy

First Date Questions About Friends & Family

7. I’d love to hear all about your family. What are they like?

Follow up question: If they mentioned someone that they’re especially close to, you can ask, “Tell me more about {insert family member}.”

People love talking about someone they’re close to.

It doesn’t matter if it’s their sister, their kids, or their grandmother, it’s just a great way to get people to open up, feel good, and have fun.

8. Among your friends, what are you best known for?

It’s a simple question, but it gets them thinking!

It’s easy to talk about yourself, and who you think you are. But when it comes to what others think about you, it makes you a lot more thoughtful.

So when you ask your date this, you might get answers that others wouldn’t have gotten. You might get to know a side of them, that other don’t.

9. If you could go on trip with anyone right now, who would you go with, and where?

This is a great way to see…

  • What kind of friends they have.
  • What kind of experiences they want to have.
  • What their friendship network is like.

Also, beyond just getting to see what kind of person they are, it’s a fun question that can help get rid of any tension that might be there.

10. Tell me about your friends, what are they like?

Follow up question: How did you guys meet?

This is such a great question to ask because it does 2 things:

  1. It shows them that you genuinely care about them, and their personal life.
  2. You get to see the kind of people they let into their life.

It can be fun to see someone open up about their friendships. Also, it’s great to know what kind of people they like hanging out with.

Maybe they’re the kind of people you’d be interested in as well, or not. It’s just a bit of exploration into who they are, and the kind of people they put around themselves.

Questions About Hobbies and Interests

A coffee date, with two cups of coffee on the table. It's a great place to ask first date questions.

11. What kind of hobbies or interests do you have? 

Follow up question: Could you tell me more about {insert hobby/interest}?

Everyone has hobbies and interests, and I think it’s ok to encourage them to share, even if they think it might be insignificant or silly.

Also, if you both have the same hobbies and interests, then this is another great places to take the conversation as well.

You can both discuss your thoughts and feelings on the shared interests, and see where the conversation goes.

Maybe your second date could be the both of you doing that hobby/activity together?

12. So what do you like to read or listen to lately?

Follow up question 1: If it’s a book, you can then ask, “Tell me more about it! I’d love to hear.”

Follow up question 2: If it’s a podcast, Youtube channel, or something similar, you can then ask, “Oh interesting, what kind of topics do they all discuss?”

This is just another great first date question to ask if you want to…

  1. Show them that you take a real interest in them.
  2. Know more about the kind of person they are.
  3. Know if you both have any shared experiences in reading certain books, or listening to any similar podcasts (as an example).

More Great Reads: 30 SMART Goal Examples for Almost Every Part of Your Life

13. What’s something you’re learning right now, or want to learn?

I promise you, this one is so interesting.

You have no idea how many times my significant other has told me about the things he’s wanted to learn, or improve in.

This kind of question helps you to know more about their interests, and what kind of life direction they potentially want to take.

Also, when they tell you, you can either see if that’s a shared interest, or it could be something you find an interest in as well. And if you do, and if things work out, you can both pursue it together. 🙂

14. What’s something you want to do, or try, but you’re a bit too scared?

Honestly, the answers for this question could be anything.

They could say:

  • Paragliding
  • Quitting their job to work their online business full-time.
  • Getting their masters.
  • Actually putting their art online, and building a following.

Any of the things they say could turn into a good jumping off point for a deeper, and/or more fun conversation.

15. What’s your favorite type of genre for movies, music, and books?

This one is IMPORTANT.

I remember talking to this guy on Facebook years ago. I was kind of interested in him, and when I asked the very sage question, “What kind of movies are you into?” 

He answered, horror. 

I can’t do it. I’ve binge watched movies like Zombieland, but at least that was funny.

If that’s your favorite kind of movie genre, I just can’t do it. 😂 

More Good Reading: 267 Good Morning Texts to Make Their Day [So Much] Better

16. If you didn’t have to work to support yourself, what would you do with your time?

This is the kind of life we ALL want. 👌

Also, it’s a fun first date question to ask! It helps them to open up, and talk about something they haven’t processed before. Or maybe they have, and they have a TON to share!

17. What hobbies would you get into if you had the time and money?

Follow up question: What do you like about {insert hobby}?

Having the right amount of time and money to go after anything, is always an interesting question.

So while their work might allow them to pursue certain hobbies, you get to learn about the ones that are currently out of reach.

Also, they might be shared interests, and this could spark some good conversation. 🤷‍♀️

18. What do you like to do in your free time?

A couple enjoying some coffee and sweets on a date.
Photo by Priscilla Du Preez via Unsplash

It’s a very easy and simple question, and it helps the conversation flow a bit better.

Also, you can see if they’re the kind of person you’d like to spend time with.

Maybe they like to hike, and do other outdoor activities in their free time. And maybe you do too! Or maybe you don’t, and you like to read books in your free time.

It’s just some good insight.

19. What are some obscure things that you’re (or were) really into?

I love learning about all the tiny personal details.

And this question is great for showing you the kind of person they used to be, or the person they are now! They’re fun details to know, and they might have the exact same obscure interests that you have.

20. Who is your favorite author?

Remember how I said it was important to ask someone what their favorite movie/music/book genre was?

It’s the same for this question.

While it can be interesting to learn about a new author, or find that you both share a favorite writer, it helps you to see what kind of things they’re into.

So maybe they like reading books by a controversial author, or they like a genre that you’re not too crazy about. It’s good to know!

21. What was the last book you really got into?

Follow up question: Tell more more about the book, what’s the plot?

This is a fun question for a first date, and you get to see what excites them.

What was it about that book that really got them hooked? And maybe you might like it too. Who knows!

First Date Questions About Childhood

22. So where did you grow up?

A couple on a coffee date.

Follow up question 1: If they said a hometown that’s different than where you’re both living right now, you can ask, “Tell me more about your hometown. What was it like growing up there?”

Follow up question 2: If they said a hometown that’s the same as where you’re both living right now, you can ask, “How do you feel about growing up in {insert town or city name}? What was your experience like?”

This one is simple, but it’s a great way to show that you care about the other person, and where they came from. You’re not just making everything about yourself, but being mindful that they’re a person too. They have a history worth knowing about.

Related: Two Thoughts on Keeping Romance Alive in a Relationship

23. Do you still keep in touch with childhood friends?

It can be fun to learn more about a person’s life, and their memories.

You get to know more about their past, and the kind of people that shaped them.

Also, it’s fun to learn about the people who have stuck it out with them over the years!

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

This first date question helps you to see:

  1. What they were like when they were a kid. Were you guys similar?
  2. How their interests have changed over the years.
  3. If their interest and passion has stayed the same.

Also, if they’re actually pursuing what they wanted to do as a child, then this can spawn so much more great conversation.

What made them hold onto this dream? Were their expectations from childhood realistic? It could go so many directions!

25. What were you like when you were a kid?

With this question, you’re showing them that you want to learn more about them, not just talk about yourself.

Also, it can be fun to learn about their past, what their childhood was like, and how they’ve changed as they’ve gotten older.

And lastly, you can get some fun stories from this question!

First Date Questions About Accomplishments

26. What are some cool things you’re proud of?

You probably have plenty of moments, or accomplishments, that you’re proud of. And it can feel so good when someone takes a real interest in you, and what you’ve done.

So you want to give, and make this person feel good too. When you go into a relationship with the mindset of giving, that’s how you grow something beautiful.

Also, it helps you see if this is someone who has, or has tried to, accomplish things in their life. Or you get to see if they’re someone who just doesn’t have a lot going on, or motivation.

27. What are some things you’ve achieved over the last year?

Whether it’s something big or small, it’s a great way to hear about what they’re proud of.

And you get to see what they’re doing with their life, their passions, and what they’re focused on.

Also, are they currently trying to better themselves, not just holding onto achievements from 7 years ago?

Personal Opinion First Date Questions

28. What are some things everyone should try at least once?

Another great first date question that shows you what what they’re into, and then you can ask them more about it.

What makes this hobby, or interest, important or exciting?

29. What fad did you never understand?

You’ve probably been there many times.

You see a clothing style, a hairstyle, or a music trend, and then think, “I don’t get it.”

And chances are, they’ve been there too.

Also, if you’ve been confused about the same fad, then it can be fun to rant together. Or if it’s not, then you just get to see how they think, and that’s fun too!

Travels & Experiences First Date Questions

A photo of a travel experience in Mexico. A great conversation starter for a date.

30. So what are some places you’d like to travel to in the next year or so?

Follow up question: Tell me about it? What would you do there?

People love talking about travel, it’s a given. But again, you’re also getting to see what kind of person they are.

Are they more adventurous? Or are they more laid back? Both are fine, but I think it’s interesting, and good to know. 🤷‍♀️ 

Also, if you’ve been there too, then can tell them about the place they’d like to visit, and give them some advice. 


31. Where have you traveled to before?

Follow up question 1: What stories do you have from when you visited {insert location}?

Follow up question 2: How did you like {insert location}?

Follow up question 3: What would you do differently if you went back? What would you do, or not do?

This is a great first date question to ask if you want them to open up a bit more. It’s a good talking point since they can start telling stories, and experiences.

Also, travels are full of regrets and surprises, so it’s kind of fun to see how they would have done things differently.

And lastly, if you’ve been there too, then you can both relate, and swap stories! ✈️ 

32. If you could travel anywhere, right now, where would you go?

Follow up question: Tell me more! Why that location, and why right now?

A super simple question, but it’s fun to see what travel location pops up in their head first.

Is it the food, the people, the scenery, or a mix? Are their sports or activities they’ve been wanting to try forever? It could go so many directions!

33. So what’s the best thing that’s happened to you this year?

If you’re talking about what’s been going on in your lives, then I honestly think this question makes a lot of sense.

You get to see what they’ve been up to, what their life is like, and it’s just kind of a fun question!

They get to talk about something amazing, and if you want, you can do the same. 🙂

34. What’s the most spontaneous thing you’ve ever done?

Hearing fun stories about other people’s crazy experiences, will never get old.

You get to hear about a 2 AM trip with friends, a crazy last minute experience while visiting another country, or even something they did to help another person.

It’s also a great way to see if they’re the kind of person who likes to have a bit of fun!

35. What amazing adventures have you been on?

Follow up question: What was the craziest part of that adventure?

Whether they’ve traveled to another country or not, this is a great one to ask.

You’re getting them to open up a bit more, and keeping the conversation light and fun.

Also, it’s a great question for connecting, and sharing your own experiences as well.

36. What’s your favorite international food?

Follow up question: What’s a {international food} dish I need to try?

Trying different cuisines, like Greek or Thai, can be very fun (and tasty).

And this question helps you to see what they’ve experienced, if you both have similar taste in food, or if they’re someone who’s up for trying new things.

37. What would the perfect vacation look like?

Now that you know where they’d like to visit, this is a great question for understanding what that trip would look like.

This kind of question helps you:

  • See if you both like to travel in the same way.
  • See what kind of travel activities they like doing.

Maybe you’re both very similar in how you like to vacation, or maybe not. Either way though, it’s a fun question!

38. What’s Your Favorite Place on Earth?

Whether it’s in Japan, or in the city right next door, you get to know a bit more about them.

It helps you to see what makes them excited, and happy in life. And you get to know more about their personal life experiences.

I promise you, this is more than just a question to get rid of long silences.

39. What’s your favorite memory?

I love questions like this.

It shows them that you actually care about them as a person, and take a real interest in their life.

Also, you could make it specific to the conversation. So for example:

  • What’s your favorite travel memory?
  • What’s your favorite memory with {insert friend name}?
  • What’s your favorite memory with {insert family member name}?
  • What’s your favorite memory from when you were in high school?
  • What’s your favorite memory from when you were a kid?

Learning More About Them Questions for a First Date

A couple talking on a coffee date.

40. So what are some of your pet peeves, or things that frustrate you?

Ok, this one feels a little random if it’s not done in the right context, but I think it’s important to know.

You get to know:

  • What makes them tick
  • The kind of people that frustrate them
  • Their personality type (and if it is or isn’t compatible to yours)
  • How forgiving, or not forgiving they are, etc.

Also, it can just be interesting. 😂 

41. What’s one of the most embarrassing things that’s happened to you?

Honestly, this is a great place for humor on your first date, to open up about your own embarrassing times, and talk about what you would have done (or felt) in their exact same situation.

Also, everyone has had embarrassing moments, so it’s a good place to relate, and know that you’re both human. 🙂

42. Do you have any pets?

Follow up question 1: Can I see photos?

Follow up question 2:  What’s it like to raise a {insert breed name if they have a specific breed}?

Why is this one important? Two reasons:

  1. People don’t just love talking about their favorite people, they also love talking about their pets. This is a great question to ask if you want them to warm up to you more. Also, it’s just good to take a sincere interest in another person’s life. 😊 
  2. If they have a certain type of pet that your’e not crazy about, then it might be something to talk to them about in the next few dates (if the first one works out). That sounds petty, but some people own certain animals that aren’t always safe around children (as an example). Or they might have a pet that makes you feel uncomfortable… like snakes. Who knows! 🤷‍♀️ 

43. So what kind of work do you do? 

Follow up questions 1: What all does a {insert job position} do?

Follow up questions 2: How do you feel about your work position (and/or workspace)?

Each of these questions not only makes the potential for a good conversation, but also help you to see what kind of person they are.

Are they ambitious? Do they have a good mindset about things? Do they complain a lot?

There is so much to learn from questions like these.

44. What’s something about you that would surprise me?

Ok, I’m gonna be honest, this one is a bit cheesy. Sew me.

But I think it’s still worth it!

I feel like this first date questions makes the other person think, and you might get to know something about your date that a lot of others don’t. 🤷‍♀️ 


45. What Makes You Unique?

This gets them to open up, and be more thoughtful.

It can be easy to get stuck in the rut of the basic first date questions. So questions like, “What do you do?” Or, “What’s your favorite hobby?”

But asking them what they personally think makes them unique, helps them to give you an answer they would never have thought about sharing.

46. What’s the worst pickup line you’ve ever heard or given yourself?

A couple on a date at a cafe, talking and probably asking questions.

First dates need humor!

Things are already stressful enough, so questions like this are neccessary.

Also, you’ve probably heard your own share of bad pickup lines (or said one yourself), so it can be fun to swap stories!

47. Who is the most fascinating person you’ve met?

You never know what kind of people they’ve met.

They could be famous, and even if they’re not, you might also find this person extremely fascinating. You get to hear their story, and be inspired yourself.

Also, it helps the conversation to go much deeper than the surface level questions you might have been asking.

Fun Fact About Going Deeper in Conversations:

I think it’s important to realize that before you go on this date, people take more of an interest in you than you think. In a study, it was shown that people actually enjoyed having deeper conversations with complete strangers. They had less awkwardness, and better experiences, when they were given deeper questions (as opposed to the group who had small talk questions).

48. Who’s been the most influential person in your life?

Follow up question 1: How did you guys meet?

Follow up question 2: What other ways has this person changed, or shaped you, in X way?

Again, if you want to take the conversation deeper, then this is a great question to ask.

You get to know how they’ve grown and developed as a person, and who’s helped get them there.

49. Who is the kindest person you know?

This could be a family member, a really great friend, or an adult that stepped into their life when they needed it most.

And then you can ask questions, and for more stories about this person. How did they show them kindness? What kind of impact did that have on them, and how they think?

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

I know what you might be thinking, “Ok, this is pretty basic.” But here me out!

This question is great for two reasons:

  1. If you’re both the same type of person, you get to hear about the kind of indoor, or outdoor, activities they do. Then you have something new to try together, or alone.
  2. Even if you’re the opposite, they might share an indoor, or outdoor, activity that might spark your interest. Who knows?

First Date FAQ’s

A tasty brunch date at a cafe. Another great idea for a date, and a good place to comfortably ask first date questions.

Ok, so now that you have some super helpful ideas to use, I think it’s important to answer some questions before you go on that first date.

I need to make sure you’re prepped. 💪 

What’s the Best Place to Take a First Date?

The best place to take your first date is a coffee shop. It’s easy going, and less formal and nerve wracking. Also, there’s a low investment. If the person isn’t very nice, then you didn’t lose a lot of money.

How Long Should a First Date Last?

You have to play this one by ear. So for instance, is this person making you feel uncomfortable? Are they making hints that they need to leave, by saying they have to be up early for work? Are you both enjoying your time? It’s ok for a date to go longer, or be cut short; it just depends on the circumstances. No need to stress over a specific amount of time.

How to Flirt on a First Date

The best way to flirt on a first date are compliments
I don’t care if you’re a guy or a girl, compliments matter, and make it specific!
If you say something like, “Wow, your hair looks beautiful,” or, “You look really good in that jacket,” they’ll like you more. I promise.

Do You Kiss on a First Date?

I wouldn’t kiss on a first date.
It gets you emotionally involved too quickly and messes with your judgement on whether this person really is worth pursuing, or not.
Do not get the hormones involved! They are liars.

How Do You End a First Date?

Here’s a general guideline for ending a first date:
. If the person is making you uncomfortable: Let them know that you need to go home, but you appreciate them taking the time to meet up with you. 
2. If you like the person, but you legitimately do need to leave: Let them know the reason why, don’t be scared. They’ll understand, I promise. 🙂
3. If you like the person, but they legitimately need to leave: Either they’re gonna let you know, or you might have to ask them. The reason being that some people have such a good time, but they lose track of how late its getting. So show that you’re thoughtful, and care about their time.

What to Text After a First Date?

Thank them for the date!
Don’t do that thing where you wait for them to text first. This isn’t a game, you’re trying to find someone you’re compatible with for the rest of your life.

How Do I Know if a First Date Went Well?

You can tell if a first date went well in two ways:
1. They say they’d like to meet up again, and they’re up for setting a date and time right then and there (if it’s possible).
2. They’re clearly flirting with you, and text you later that evening, or the same day.

Now, these are just a few good ideas for first date questions, but I hope they helped you out a lot!

I know that it’s not always the easiest when you’re meeting up with a person for the first time, but these ideas should make it a little easier.

PS – Let me know how it goes! I can’t wait to hear about it!

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Chasing Foxes was started in 2016 as a way for Grace and her husband, Silas, to start traveling. However, they started to realize that they had a passion for improving themselves, and wanted to help others level up their lives as well. So whether it's with cooking, travel, or staying healthy, they want to help you better your life bit by bit, as they do the same.

Featured Lifestyle Relationships Wellness

Silas & Grace

Chasing Foxes was started in 2016 as a way for Grace and her husband, Silas, to start traveling. However, they started to realize that they had a passion for improving themselves, and wanted to help others level up their lives as well. So whether it's with cooking, travel, or staying healthy, they want to help you better your life bit by bit, as they do the same.

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