20 Deep Questions To Ask a Guy Before Dating – To Understand Him

If you were looking for deep questions to ask a guy before dating, you are at the right spot. We have written some of the most in-depth questions that will help you to understand and know more about his personality. These questions are not hard and fast rules for judging someone. The questions will help you understand his thinking and mentally about different things, which will help you a lot in your future.

Deep Questions To Ask a Guy Before Dating
Deep Questions To Ask a Guy Before Dating

Question 1: If you get a chance to move elsewhere in the country, which city would you like to move to?

If he is planning to move somewhere in the future, he must have planned it already in his mind. You must ask him this question to know his plans without directly asking him.

Question 2: Do you have any clear childhood memory?

We don’t remember everything while growing up. But some events are so much deep that we can’t forget them.

Question 3: What is your all-time favorite idiom?

If you guys want to smile, ask this question. It’s a light question and easy to answer the question. Also, try these good questions to ask a guy.

Question 4: What was your favorite website when there were no social sites? e.g., Facebook, Twitter, etc.

If he is from the ’90s, he must know the answer to this question. Obviously, the new generation doesn’t know much about Msn, Yahoo messenger or chat rooms, etc.

Question 5: Do you hate any celebrity?

Yes, we do hate people for different reasons. And celebrities are too public, so people often hate them for other things. these are the deep

Question 6: What you notice most in people?

We all observe different things while meeting with someone. But everyone has his own style of observation. You must know this about your guy how he notices people.

Question 7: What specific thing quickly makes you angry?

To know him better in the sense of anger, you must ask this question to your guy. It’s a fundamental question for you, from our list of Deep questions to ask a guy.

Question 8: Suppose you were alone at home, and your home got on fire. You can only save one thing, what would it be?

If you are curious to know the most important thing for him in his house, ask this question to him.

Question 9: What weird food combination you liked the most?

It’s possible because we sometimes make our own flavors in food.

Question 10: Have you ever traveled somewhere outside our country?

Before starting a relationship, you must know his travel history. With this question, you will see if he is a frequent traveler or has not visited anyplace outside your country.

Question 11: What is your favorite mobile game?

It is just a fun question to ask a guy. He’ll also enjoy describing the game to you.

Question 12: What is the Worst Advice you received from someone?

Sometimes people around us misguide us and gave us the wrong advice. We never forget such things and also want to save others.

Question 13: What is the best advice you received from someone?

Like the worst advice, we also get useful advice from people around us or from our friends. We also feel great while sharing that piece of advice with others.

Question 14: What’s the most useful skill you’ve ever learned by yourself?

Guys enjoy learning new skills while they are teenagers. After that, the new learning process slows down, which useful skill he had might help you in the future. You should also try these existential questions if you want to know more about beliefs.

Question 15: What is your favorite trend of all time?

Trends are very common these days due to social networks. E.g., fidget spinners, etc.

Question 16: What was the last stupid thing you heard from someone that made you laugh?

If you guys are in the mood to laugh, it’s one of the best questions to talk about and laugh. If interested, you should try more funny questions.

Question 17:  Do you believe in global citizenship?

Global citizenship means the world as a single country. Global citizenship is giving rights to people to travel or live anywhere in the world. Find out his thoughts on global citizenship.

Question 18: What can you eat best at $5?

Suppose you want to hang out with him and don’t want him to spend too much on you. Ask him this question and let him take you to have that thing in less than $5.

Question 19: Which movie has the best villain portrayed as a hero?

Sometimes movie villains are portrayed as heroes. Ask him this question to know about his interest in movies.

Question 20: If you can go back in the past, which invention would you like to name for yourself?

It’s just a fiction based question to have an interesting discussion with your partner. If you have time, have a look at the questions we have from Reddit.


We hope you enjoyed our prepared list of questions. Thank you for taking the time and reading all our deep questions to ask a guy before dating!

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