20 First Date Questions That’ll Help You Both Feel Comfortable

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.

Meeting up with a person for the first time honestly isn’t that fun. I mean it can be, but then you have to overcome the nerves and overwhelming thoughts of, “What if this is awkward?”

And I feel like this gets even worse when it comes to dating someone for the first time. 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 have the right ones, and sadly, there are so many bad ideas online that don’t help the situation.

I get so tired of hearing ideas for conversation starters that make me think:

  • “Why would I ever bring that up?” 
  • “That’s so awkward, who asks that?”
  • “I would have to be a middle schooler to start a conversation like that.”
  • “If I asked that person that question, I’m pretty sure they’d cut the conversation short, then immediately get on Facebook and block me.”

So, I’m here with an actually useful list of questions for your first date that will help ease your anxiety before you meet up with this person.

Oh, and I also have two good posts that will help you on your first date as well!

The first one is on conversation topics and conversation advice, and the second one is on tips on how to make friends as an adult. Both give good guidance on how to make this first meeting flow without the anxiety that awkward moments might happen.

Also, before we begin, I think it’s important to know that before you go into this date, people take more of an interest in you than you think. In a study done by the American Psychological Association, it showed 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.

So in the end, things aren’t always going to be as bad as we make them out to be, and people really do want to know more about you! I think that’s incredible. ❤️ 

Now let’s get into the questions for a first date. 🙂


A Helpful List of First Date Questions

A photo of a girl putting her hands on the back part of the guy's neck and the guy has his hands around her back. They're on a date and looking romantically at each other as the sun sets. The text for the girl has her asking a first date questions and it says, "If you could be any insect, what would you be?" And the text for the guys says, "I wanna go home."

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

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!

Related: 13 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 like 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 for the both of you to know that instead of wasting more of each other’s time.

I know saying, “Wasting more of each other’ time” sounds harsh, but it’s honestly true. If you’re not compatible, then you’re not compatible. 🤷‍♀️ 

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

A photo of a couple on a date at a cafe. She's looking at him and the guy has his back to the camera.

Whether it’s a project or even a financial goal, this is a great conversation starter on a 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! 🙂


4. 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 personally think it might be insignificant or silly (if they’re already feeling insecure of course).

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.

5. 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 it also helps you 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.

6. 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 from the job they already have. It gets them thinking and shows that you’re actually interested in what they want with their future.

Or if they are 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 allows you to get to know them better. 👍 


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, their grandmother, it’s just a great way to get people to open up, feel good, and have fun.

8. So where did you grow up?

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 for you?”

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 and they have a history worth knowing about.

Related: Two Thoughts on Keeping Romance Alive in a Relationship

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

A photo of a couple on a date, sitting at a table with hot drinks and chocolate muffins. You can't see their faces, but you can see part of their arms. The girl is holding a partially eaten chocolate muffin, while the guy has his hand on a hot drink. There's a plate of four extra chocolate muffins in between them. There's also a plant by the big window where the table is, and the window is letting in a lot of light.

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 what 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).

10. 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 get to know more about their interests and what kind of direction they want to potentially take in life. 

Also, if there is something they open up about, you can either see if that’s a similar interest to you or it could be something you find an interest in as well. And if you do, you can talk to them about it and if things do work out, you both can pursue it in the future! 🙂

11. 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.


12. 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. 😂 

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

A photo of a couple on a date. They're both sitting next to each other in a field on what looks like very old wooden train tracks. They're both laughing a lot about something together.

Honestly a great place to both laugh on your date, open up about your embarrassing times, and talk about what you would have done or felt in their exact situation.

Also, everyone has had embarrassing moments, so it’s a good place to relate and know that the both of you are humans. 🙂

14. 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 closest family members or friends, they also love to talk 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 you want to talk to them about in the next few dates (if the first one works out). That sounds so petty, but sometimes some people own certain animals that aren’t always safe around children, for example. Or they might have something that makes you feel uncomfortable like snakes. You never know! 🤷‍♀️ 

15. 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. 


16. 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 experience or not experience?

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 do things differently.

And lastly, if you’ve been there before too, then you can open up, relate to them about it, and swap stories! ✈️ 

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

A photo of a girl in a white blouse sitting at a white marble countertop at a hip looking restaurant. She's looking at her date as he's talking. The date is off camera, but you can kind of see his hand. She also has her hand on a cup of coffee, and the other hand looks like it's slightly playing with her hair.

All of us have moments or accomplishments that we’re proud of and it feels so good when someone takes a real interest in us and what we’ve done.

You want to give and make this person feel good. 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.

18. 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. 🙂

19. 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 one makes the other person think and you might get to know something about your date that a lot of others don’t. 🤷‍♀️ 


20. So what’s your favorite type of genre for movies, music, and books?

Ok, I need to say, this one is IMPORTANT.

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

He answered, horror. 

I can’t do it guys. 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. 😂 

First Date FAQ’s

An overhead shot of a table at a restaurant where people are probably eating on a date. On it is a menu, two drinks, and two main dishes. One dish looks to be a healthy bowl with many colorful ingredients, while the other is a steak, with a salad, fries, and dipping sauces. There are also napkins, a plant, silverware, salad dressing, a candle, and salt and pepper on the table. The table is also a light wood.

Ok, so now that we have some super major and helpful questions listed, I think it’s important to answer some questions before you go on this first date.

We need to make sure you’re prepared. 💪 

You don’t need to be going into this all nervous. You’ve got this and I’m gonna help! 👍 

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

The best place to take your first date is a coffee shop.

Here’s why:

  • It’s easy going. Less formal and nerve wracking.
  • There’s a low investment. If the person isn’t very nice, then you didn’t lose a lot of money. 🤷‍♀️ 
  • If the person is a jerk, you can just walk out. No need to stay around. The coffee has already been paid for. 

Now I’m not saying you have to do this, but it is a thought!

How Long Should a First Date Last?

Honestly, this is one you play by ear. I wouldn’t stress out about it too much, but there are some important things to think about.

Things to consider:

  • Is this person making you feel uncomfortable? Don’t stick around because you feel bad; it’s ok to not prolong the date longer than you need to.
  • Is your date making hints that they need to leave by saying they have to be up early for work (as an example)? Then it’s ok to stop the date there.
  • Are you and your date both enjoying your time? Then it’s ok to go longer, but just be intentional to watch for any cue they might give that they need to head home.

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 will like you more. I promise.

Don’t make it weird or cheesy, keep it simple and sincere. That’s how it works, I promise.

Do You Kiss on a First Date?

Photo of a teenage boy and girl on a first date. They're both sitting by a small lake in a park and facing each other. Their backs are to the camera. It's also a sunny day and they're sitting in the shade.

I wouldn’t kiss on a first date.

It gets you emotionally involved too quickly with someone 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?

Depends, but here’s a general guideline:

  1. 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 say something like, “Hey, I just wanted to check up and see how you’re doing. Do you need to start heading home? It’s not that I don’t want to talk more, but I know we’ve been together for a few hours already and I want to respect your 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 compatable with for the rest of your life.

Just focus on making them feel good, and if they don’t return the same kind of energy and don’t want the same from you, then don’t waste your time on them. 🤷‍♀️ 

How Do I Know if a First Date Went Well?

You can tell if a first date went well in a couple of 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.

And that’s it.

Of course, there are obvious signs that the person might not like you, and you should be looking out for them. Example: looking at their phone repeatedly, being dismissive of your answers, etc. etc.

But in general, if one or both of those two things happen, then I think you’ll know that it went well. 🙂

Now, these are just a few good ideas for questions for first dates, but I hope they help 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 bit easier.

Also, if things don’t go well, then don’t be hard on yourself! You’re figuring things out and you are going to find the right person for you. ❤️ 

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

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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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