20 Questions to Ask on First Date

“Ten Things I Hate About You” is a cute and funny movie. We all want our dates to sweep us off our feet. But, we don’t want a date with 10 things we hate about them. That’s why it’s important to ask the right questions on the first date. You want to learn about your date but you don’t want to sound like a detective. So, how do you keep it light and fun but also learn about your date? Here are 20 questions to ask on a first date!


What’s your favourite cuisine? What do you love to eat?

As creative as initial dates can be, sitting down for food is universal. You want your date to plan a fun activity or a romantic walk, that’s for sure. But, you want to be able to sit down and have a conversation with your date as well. Do you love the same foods? Brilliant, you can know what to cook to impress your date or where to take him/her if you want to see him/her again. 


What was the highlight of your week so far?

While it may seem random, asking about the highlight of someone’s week is not the same as talking about the weather. It is the first date, you want to keep things light; but, you want to know if you connect with your date, if you have the same likes and dislikes. By asking about the highlight of their week, you learn about what they value most without having to directly ask! Does your date love basketball a lot more than you do? Is you date a big foodie like you? Is your date really extroverted and you are not? 


What’s your dream vacation destination?

It might give you something mutual to talk about if you have the same dreams. Or, talking about different countries and cultures might be a gateway into your date’s life and yours. The most important thing is to get to know your date in an organic way without sounding invasive or rehearsed. 

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What’s an embarrassing thing about you…something you don’t share with others?

Laughing connects people. Laughing helps us kick back and relax. When we kick back and relax, we can be ourselves. First dates are often awkward when we are too wrapped up in what our date thinks of us. Listening to a silly confession will help you and your date remember that your date is trying to impress you as much as you are trying to impress them. 


Why did you go on this date with me?

While this is not a conversation opener on a first date, there is nothing wrong with understanding your date’s plans and making sure they align with yours. Maybe they simply want to get to know you, maybe they are looking for something serious or maybe a friend of yours mentioned how great you are. Whatever the reason is, make sure you are both on the same page. 


When was the last time you went on a date?

Is your date into serial dating? Have they been in a serious relationship before? Are they still hung up on an ex? This question can help you segue into their dating history without coming off to strong. 


What was the worst date you’ve ever been on?

It’s easy to pretend that you are having a good time on a first date when you don’t want to hurt your date’s feelings. Asking them about his/her worst date will show you what not to do if you want to win a second date! He hated going bowling, don’t ask for a bowling date. She hates waiting and unpunctual guys, don’t be that guy! 

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What’s your favourite book of all times?

Keep simple questions coming, but questions that help you learn about your date. Don’t ask about their favourite colour or their favourite store- not very informative in the dating world. But, what they like reading most will give you a peek into their mind. 


What’s your favourite season?

It’s easy to imagine 15 more dates in your head when you are having a good time. But in reality, you don’t know enough about the person to know whether they will enjoy what you enjoy or not from the first date. Are you crazy about skiing and skating? Are you planning all these dates in your head and fantasizing about all the fun you are going to have only to find out that your date hates the cold? 


If you could be an animal, what would you be?

Sillier questions will help you and your date be comfortable and be yourselves. But, by asking your date to elaborate on the why, you will get to know a little bit more about the traits they value most in a less staged way. If you date says he/she would want to be a horse because they love green pastures and the farm life, then know that your date values a quiet and quaint life above most else. 


What are your top 3 pet peeves?

It is harder to talk about what we love. But, people usually know what annoys them most. Asking your date about their biggest pet peeves can help you understand whether you see eye to eye or not. 


What are your hobbies?

You want to know your date’s hobbies, what he/she does in his/her free time. The first few dates can be exciting when you are getting to know someone new. But, what about later down the line? Do you enjoy the same things? Will you enjoy doing the same things together? 


Did you grow up in the city?

If the answer is yes, maybe you have the same favourite restaurant or coffee shop? Maybe your cousins know one another? And if the answer is no, you can get to know your date a little bit more. Why did you move? What do you miss about where you grew up? When people talk about personal experiences, they connect more, especially when they are not talking about a topic where they need to impress. 

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If you win the lottery tomorrow, what would you do?

This is another casual way to know about your date values most in life. Will they donate some money to charity? Do they want to travel the world? Do they want to go back to school for more education? They will essentially tell you about some of their dreams. And who knows, maybe you guys share the same dreams! 


What music do you listen to?

Not a dealbreaker in any shape or form. But, it is nice to know if you have the same taste in music. Maybe you can plan a road trip down the road or maybe you can go to a concert together in a week or two. 


Do you have any siblings?

You might want to learn a little bit more about your date’s family and personal life. But you can’t outright ask them about their upbringing. Asking about siblings can help you share stories about your upbringing and it might invite your date to divulge a little without you having to pry. 


Do you have a lot of friends or a trusted few?

It is good to set your expectations and know if you and your date lead the same lifestyle. If you are very extroverted with a lot of friends, you want to make sure your date will enjoy the same lifestyle before you start seeing him/her for a second, third and fourth date. Friendship and what a person values in friendship can be a good indicator about how they behave in relationships too. Does your date value his/her alone space and time? Do they think they are too busy to have many friends? 


What is the most romantic thing you’ve ever done?

It’s nice to get a glimpse into your date’s relationship style without asking too much about the past, especially on the first date. If you love roses and candlelit surprise dinners, it might be nice to know what your date is capable of from the first date. 


Would you rather cuddle and watch a movie or bar hop around town? 

There is nothing more disappointing than expecting your date to plan an elaborate adventure when all you keep on doing is going out for dinners, coffees and movies. This could simply mean that one of you is more of a homebody than the other is. You can both be great people, but with completely different lifestyles. Ask from the first date before you go any further. 

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If you could meet one dead person, who would that person be?

Open ended questions are good for conversation flow. Everyone hates awkward silence. When your date digs deeper into who they want to meet and tell you the why story, it will allow him/her to speak freely and it will give you both more topics to discuss organically. 

Keep it casual and effortless. But, don’t shy away from getting to know if your date is worth your time. Give these questions a try and go enjoy your first date!