Questions To Ask On A First Date

Off on your first date? Congratulations (for now)! 

We all know going on a first date can be exciting and nerve-wracking at the same time, especially if you’re dating a Gen Zer – Young adults in their 20s. Gen Z people are overly cautious yet anxious, according to the Pew Research Center. This makes many youngsters wonder what questions to ask on a first date. 

Yes, dating isn’t easy, and the worst is if you’re dating for the first time or if you’re an introvert, it can feel like a job interview for both of you.

This can make asking first-date questions challenging, never mind directing those dreaded awkward silences. So what can you do in this situation? 

Luckily, there are some open-ended questions available online that can help you break your awkwardness on your first date. 

Not sure where to start? This blog has a list of 16 interesting questions to ask on a first date, which will definitely help you break the ice and get the conversation going. 

16 Questions to Ask On A First Date

Dating is not just about you. It’s a two process. 

Let’s face it. Getting to know someone through questions can look tricky without feeling like a job interview. But with a list of a few first-date questions in mind, you can make it go smoothly. Here are some interesting questions to ask on a first date. 

1. How do you like to spend your free time?

By asking this question, you can determine what the person is most passionate about and what they enjoy doing for fun.

It could be painting, spending family time, attending clubs, reading a book, cooking, playing with pets, or even walking. Never say sleeping; it could be a red flag, and the other person may not like it. 

If their interests don’t match yours, it is better to know now than later on down the road.

2. How close are you with your family?

Another way to get the scoop is to ask about their family life and how close they are. 

This is a must-ask question to ask on a first date as some people believe it’s important their families get along with each other. Ask about their background, siblings, where they grew up, and how close they are as a family. 

Try not to judge them quickly since people come from all walks of life. The first date is the perfect time to get to know each other’s family and help you realize the potential a relationship has and the way your date relates to the people closest to them. 

3. What’s the best book you’ve ever read recently? 

If you’re a bibliophile, you can start asking about your favorite books, fiction, novels, romance, authors, etc. If your date turns out to be a book lover, conversion may get more interesting! 

But, if you’re concerned that the conversation will be forced, you can always frame it around favorite books, podcasts, music, or cuisines. Soon, you’ll be engaging in a talk while also discovering more about each other’s likes and dislikes. 

4. What’s your favorite movie or show? And why? 

They say people’s interests are reflected in what they like to watch. 

This is an easy question that is not too deep or intense. Ask about their favorite movie or TV show and what made them like it. This will give you an idea of their viewing tastes and their perspective based on that movie.

Believe it or not, you’ll learn a lot about the other person by asking this simple question.

You can also talk about a recently released movie and share your views. And if neither of you has seen anything new in a while, you might have a great second-date idea! 

5. What’s on your bucket list?

Speaking of going deeper, asking about a bucket list is a good way. In fact, talking about a bucket list may turn out to be a brainstorming session!

Finding out their goals, dreams, and plans can tell you a lot about who they are as a person. By asking this question, you can easily figure out if you have a future that aligns with theirs. 

6. What are you looking for?

This question is to assess what they are looking for. It doesn’t have to look like an interrogation. It only makes logical sense to ask about each other’s dating intentions.

You won’t waste time going on the second date once you realize this from the first one. 

Casually ask them what brought them to the dating site you might have met on or what type of relationship they are looking for. Are they doing this to get married in a short time or just a casual relationship? 

While it may sound like a risky question to ask on a first date, it’s important to get an idea of where your date sees themselves in the future. If they are fairly unwilling to open up about this, then it’s surely a red flag. 

The same goes for your case. If they ask you, be open about your response and unapologetic about what you’re looking for. After all, you want to make sure you’re on the same page! 

7. What makes you happy? 

Okay. A Pause. 

This may look like an easy question, but it is quite tricky to answer. When you ask this question, there will definitely be brief silence. 

However, asking your date what genuinely makes them happy is helpful in understanding the way they think and live. They may respond with things like family time, playing sports, some kinds of jewelry, or simply sleeping.

8. Are you a cat person or a dog person? And why? 

Some people love cats, while others like dogs. Some love both. This is a good way to initiate conversation without being awkward. Ask them why they would prefer dogs/cats. 

This classic conversation can tell you a lot about their personality, emotions, and lifestyle. 

If they are a dog person, that means they have a kind, loyal, and playful personality. If they are a cat lover, then they seem to have a loving and interesting personality. 

9. What caught your eye about my profile?

This is a good question to ask on a first date as it gives your date the perfect opportunity to compliment you. The same goes for your case. Moreover, the conversation will likely lead to other topics. 

Let’s say you have a mutual interest in a particular singer; you can bond over that. Asking in this way is just a more thrilling and flirty way of bringing up the topic. 

10. What’s the most embarrassing thing that’s happened to you?

Ah! This question may sound odd. But try it out; it’s a fun way to pull out if there’s silence in your conversation. If you talk about awkward moments, it shows modesty, vulnerability, and a sense of humor. 

But yeah, firstly, you must check if they’re comfortable sharing some embarrassing moments. Read the room and try not to laugh hard at his story, as it may make them insecure. 

 11. Who are your best friends/closest people?

There is a popular saying that you are the sum of five people you spend the most time with. That’s why it’s important to ask about their closest friends, even if they have just one best friend. This will give you a decent idea as to what type of person they are. Pay attention to how they talk about other people.  

This could be an eye-opening question and one that gets a conversation going about the value of friendship in your lives. It’s very pleasing to listen to someone describe the people they love and care about. 

12. Where would you like to travel first and why?

This is a very common question among people who go on first dates. If you’re a keen explorer or traveler, it’s obvious that you will want your date to have the same interest.

Start asking about their favorite vacation spot and where they would like to travel.

By leading with this question, you may better understand your compatibility in a more discursive way that doesn’t put them on the spot.

13. What’s something you’re really proud of lately?

This may sound a little sheepish or job interview-y, but it’s a great question. Ask them what decisions they have made that they are genuinely happy about. Maybe they are proud of landing their dream job, hitting a goal, or learning how to make lasagna! 

Again, it can give you insight into what is meaningful for them and might show their values. And you can share yours, too! 

14. What’s your hidden talent? 

Less talk, more actions. Everyone has a hidden talent, and some of them can be pretty funny. Ask this question to give the other person a chance to surprise you. Also, be prepared to show off your talent, too. 

Maybe they are secretly good at something like solving the Rubik’s cube or baking, anything weird that not many people are aware of. This will definitely help you have a great time with your date.

15. What’s your pet peeve? 

We all have pet peeves – little things that annoy us. Ask them about the things that get on their nerves and what bothers them. Are they getting laid back and easygoing, or do they tend to be easily stressed? 

Learning about pet peeves gives a better understanding of some of the things that make a person tick. Besides, it’s a good way to be open and honest with each other from the beginning. 

16. Would you rather…?

This is the best and most fun way to spark your first date. There’s a chance your fate might get bored answering too many questions.

If such is the case, you can start playing this fun game. Would you rather questions will help you both open up to each other – even if it’s in weird and quirky ways?

Questions like Would you rather… eat pizza or ice cream for the rest of your life? Go to the mountains or the beach? Watch horror movies or Anime? Would you rather be a dog or a cat? Go scuba diving or bungee jumping?

What Not to Ask on a First Date?

When listing down the questions to ask on your first date, it’s also important to be aware of some juicy questions that you must avoid asking at all costs. 

Apparently, first dates should be all about getting to know the person on a lighter note. It’s your first meeting, after all! Hence, there are some questions you should never ask on your first date.  

  1. Why are you single?
  2. Do you think your parents will like me?
  3. What qualities are you looking for on a date?
  4. What dating apps are you on?
  5. Are you seeing anyone else?
  6. Do you want to have kids in the future?
  7.  Why did your last relationship end? 
  8. How many people have you slept with? 
  9. Do you have your own house?
  10. Do you normally eat this much?
  11. How much do you weigh?

Final Reflections!

The truth is you can literally talk about anything you’re in the mood to make conversation on your first date. That said, having a list of questions to ask on a first date beforehand will help you break the ice, get to know the person, and develop a connection with them.

First, go for open-ended questions that start with what, how, and when to keep your conversation engaging.  

It’s important to keep in mind that it’s not just about knowing the right questions to ask on a first date but also how you engage with the person, how you respond, and how you carry yourself. Be confident and ask the bare minimum questions! 

Another important note to consider is that your first date isn’t for you to decide if this person is “The One,” and the topics discussed during this first meeting should reflect this. 

Good luck! 


1. What is the most important question to ask on a first date?

Ans: The first and most important question to ask on a first date is about their interests, hobbies, likes, and dislikes, such as favorite food, sports, destinations, movies, etc. Talking about such topics is the best way to connect with your first date. 

2. What flirty questions to ask on a first date? 

Ans: Some of the flirty questions you can ask on a first date are:

  • What is your funniest dating story?
  • What is your favorite romantic movie?
  • What is your love language? 
  • What are your biggest turn-ons?

3. Should you ask serious questions on a first date? 

Ans: No. Your first date is just a meeting to see if there is chemistry. It shouldn’t be too intense and serious. So, asking serious questions wouldn’t be appropriate. Otherwise, it will feel like a therapy session. 

4. Is it bad to kiss on a first date? 

Ans: There’s no definitive answer when it comes to kissing on a first date. It all depends on your instincts, the vibe, the connection, and how comfortable you are feeling with them.  

5. What are the biggest red flags on a first date?

Ans: It’s important to notice the red flags when you’re on a first date. If they frequently keep checking their phones, talk only about themselves, bring up sex talks, or are rude to others, it’s a sign your date isn’t compatible. 

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