20 intelligent and interesting questions to ask your crush

It is not always easy to have a first date with someone you have a crush on. Whether you know them from school or you’ve just met them in Tinder, a crush is fun and new. Although we like the person very much, it is easy to lack topics of conversation, either because of shyness or because we know very little about the person standing in front of us. It is then easy to talk about the temperature or worse, to fall into an embarrassing awkward silence. Fortunately, it is possible to avoid these unwanted situations by preparing a few questions to ask your crush before your first date. Without memorizing them, you can keep them in mind before your date so you don’t miss any interesting topics of conversation. Do not hesitate to modify the questions as you wish; after all, they should represent you!

“Do you plan your holidays several months in advance or are you more of the spontaneous vacation type?”

Although this question may seem trivial, it can reveal a lot about a person. Indeed, for some people, organizing a trip (and even organizing in general) can be very stressful and can be very distressing. Lack of planning can also create this kind of anxiety in others. If you are one of those people who need a lot of structure and organization and who doesn’t like to be too adventurous, you should probably avoid seeing someone who is running away from agendas.

“Have you ever done anything completely “crazy” for a person when you were dating them?”

It may be interesting to ask the person you are seeing, especially on a first date, about their past relationships. You will learn more about their personality, but also about their love history. Was he/she a person in a long-term and loving relationship or was he/she rather a person who was constantly in short-term relationships? You may find out soon enough!

“How would you like to be remembered later?”

If you see that the conversation with your date is going well and the topics are flowing one after the other, you can always ask them this question. Not only is it original, but it also allows us to learn a lot about the other. Indeed, you will know what is really important for this person, namely their values.

“If you could travel back in time, what advice would you give yourself?”

By asking this question, you will be able to learn a lot about the past of the person you are dating, but also about how they perceive their past. This will give you a good indicator of how they have matured through their different life experiences. You will also know how your date faces the obstacles that scatter its path. This question is therefore interesting in several respects!

“In your opinion, is it better to communicate by text message or verbally?”

Again, this simple question can say a lot about a person. Although we are in an era where technology is omnipresent, some people barely use text messages to communicate and are more likely to discuss verbally to avoid misunderstandings. It will also allow you to know which method of communication to use with your date, which can always be practical.

“What is the date of your dreams?”

By asking this question, you will learn more about each other’s tastes and be able to plan an outing much more easily if necessary. In fact, if you know that the other person prefers Japanese restaurants to French-inspired ones, you are one step ahead, aren’t you?

“Can you name one thing that makes you a little anxious?”

If you are really comfortable with the person, you can always ask them what makes them anxious or shy. Sometimes, revealing part of one’s vulnerability helps to create a certain understanding and, eventually, intimacy.

“Have you experienced anything embarrassing recently?”

Again, you must be comfortable enough with your date to ask him/her such a question, as it exposes them directly to their vulnerability. Of course, you will immediately see if the person you are dating is humble and has a good sense of humour, which is not something to be overlooked!

“What do you like most about your friends?”

This is an extremely interesting question to ask your crush. You will learn about the people around them and the importance that their loved ones have in their lives. This is another good way to find out what the other person’s predominant values are, as they are most often found in his or her friends. Do they spend all their free time with their friends? Questions about their friends will help you learn more about them.

“If you had the opportunity to invite anyone, dead or alive, to a dinner at the restaurant, who would you choose?”

While this may seem like a crazy question at first glance, it is very telling. It reveals a lot about a person, including their interests, their vision of life and their political opinions, depending on who they decide to invite. This is, without a doubt, a question that can open up a wide subject of conversation, provided, of course, that you answer it seriously!

“What’s your favourite hobby?”

Take the time to ask your date if they have any hobbies. You may be surprised by their answer and find even more in common with them. It is also always pleasant to know how the other person’s daily life is structured.

“If you could fly to any destination with an unlimited budget, where would you go?”

It is obviously unrealistic to fly out on a whim without taking your budget into account. At least, few people can afford to do so, but it is certainly pleasant to imagine that it is possible. To ask this question is to let the other person tell us about their dreams of travel and surprise them in a spontaneous way!

“What has changed your life the most and why?”

This question to ask your crush will tell you a lot about them. Indeed, you may discover that a significant encounter has helped them through several difficult ordeals or that the loss of a loved one, although stressful, has made them feel better about everything else. Otherwise, maybe a solo trip in their twenties has completely changed their life!

“What would you do if you won the lottery?”

Some people would be inclined to spend their wealth quickly while others preferred to invest the amount earned in a bank account. In any case, this question can reveal a lot about a person’s values and priorities.

“What do you think is the most beautiful compliment to give or receive?”

By asking a question like this, you will know if the person in front of you is more interested in the external or internal qualities of others and if their values are consistent with yours.

“Do you have a good relationship with your family?”

This might sound like a very personal question but it is also an important one. You want to know whether your crush has a good relationship with their parents or not, if they had a nice childhood, etc. If you’d like to have a long term relationship with this person, you need to know how they treat their family members. Are they close to their siblings? You’ll find out a lot of things about them by asking this good question.

“Is there something that can always make you smile, no matter how sad or mad you are?”

It might be their favourite food, funny habits they have, their wildest night, or some fantasies! This is the type of fun questions you can ask once you’ve both answered the basic questions. Dating questions don’t have to be serious all the time, even the less serious ones can give you insight into your crush’s true self. The answer to this question could decide whether there is a second date or not!

“How do you unwind?”

If they answer “I never unwind” then you’ll instantly know they might not end up as your significant other. Would you really want to be with someone who is always working and never takes any free time for themselves? They might have their dream job but that shouldn’t result in living a boring life.

“Do you have short-term and long-term goals?”

What if your crush has no goals in life? Can you see yourself with some who has no ambition? They might be very attractive and be the funniest person you’ve ever met but one day you might get annoyed and not feel attracted to them anymore if they are happy with a boring life with no meaning.

“What do you choose between love or money?”

A bit flirty, a bit silly but always fun to ask, this question can tell you a lot about someone. Some people don’t mind knowing their crush cares more about money than love.

These simple questions to ask your crush on your first dates can, therefore, help you have an interesting conversation with your date while allowing you to get to know them well. However, don’t forget to adapt the questions to the discussion and your personality!

Cover photo: @ourbackpackjournal | Instagram