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24 First Date Questions to Ask the Guy You Like: Deep First Date Questions

24 First Date Questions to Ask the Guy You Like: Deep First Date Questions

24 First Date Questions to Ask the Guy You Like
  1. What is your unique trait?
  2. If you could only eat one dish for the rest of your life, which would you choose?
  3. If tomorrow was your last day on earth, what would you do during those 24 hours?
  4. If you could make three wishes, which would it be?
  5. What are some random fun facts about you?
  6. What is the thing you are most passionate about?
  7. If you were to lose one of your 5 senses, which one would you choose and why?
  8. What’s your idea of a great date?
  9. Would you rather…?
  10. Do you have favorite people?
  11. Do you have a favorite place?
  12. What’s the most embarrassing event you’ve ever been through?
  13. What is your favorite thing to do on weekends?
  14. What is your guilty pleasure?
  15. What is the thing you are most proud of?
  16. What helps you truly relax when you are stressed?
  17. What makes you laugh the most?
  18. What is the scariest thing you have done?
  19. If you were forced to eat in a Fast-food Restaurant for the rest of your life, which two places would you choose first?
  20. What is the thing you are most grateful for?
  21. What is the thing you are most afraid of?
  22. What is the best thing in your life right now?
  23. If you could only watch a movie for the rest of your life, what would it be?
  24. What is your favorite social network?

So you’re finally going on a first date with the guy you like. Girl, that’s one tremendous feat you’ve accomplished. Congratulations! Now, let’s get down to real business.

You have probably picked out the best dress and shoes that will completely leave him breathless, at least for a while. That’s good thinking. But when it comes to the actual conversation, our tongues become tied. All that is about to change with this article. Here, I’ll be revealing to you great first date questions you can ask the boy you like. Not only will you impress him with your soulful eyes and amazing personality, but you will also show him how incredibly beautiful your mind is. Let’s go!

24 First Date Questions to Ask A Guy

24 First Date Questions to Ask the Guy You Like
1. What Is Your Unique Trait?

This is a great conversation starter. Get him to talk about himself and what he considers a unique trait or talent. Get ready with your own answer too because he might decide to ask you the same question. From this question, you would discover what his hobbies and talents are. If played very well, it could even lead to making plans for a second date.

2. If You Could Only Eat One Dish For The Rest Of Your Life, Which Would You Choose?

Instead of just asking him what his best food is, add a little spice to the question by putting it this way. Most people never have one real answer to this question, but if he does, then it’s good information. Might come handy in the future.

3. If Tomorrow Was Your Last Day On Earth, What Would You Do During Those 24 Hours?

This is another great question that would help you understand what is most important to him. Usually, people would use the last 24 hours of their lives to do something they’ve always wanted to do, or spend time with the ones they love the most. It is a fun question that might lead to others. Don’t forget to make mental notes of these answers. They could come in handy if there are future conversations.

4. If You Could Make Three Wishes, Which Would It Be?

The three wishes question is an old-time classic and it helps to reveal what your date’s greatest wants are. This could be a great conversation starter and might also help when you need to get gifts for him in the future.

5. What Are Some Random Fun Facts About You?

Simply asking him “Tell me what I do not know about you?” is plain and uninteresting. It leaves too much room for so many answers and could be a conversation killer. Framing the question in this manner will help him think and come up with some weird and fun details about his life.

6. What Is The Thing You Are Most Passionate About?

This is a very deep question, one you should ask when you’re certain that he is comfortable in your presence. Most people are reluctant to reveal the things they really care about, so you might want to save this question for much later during your date.

7. If You Were To Lose One Of Your 5 Senses, Which One Would You Choose And Why?

This is a tricky question. It will require a lot of thinking and will lead to fun bouts of laughter.

8. What’s Your Idea Of A Great First Date?

It’s quite obvious that you both are on a date, but asking this question will help you understand what his values are. In answering this question, he will tell you the things he thinks are more important and the ones he could care less about. Hopefully, your tastes align. Does he prefer outdoor dates to indoors?

9. Would You Rather…?

This kind of question will have you making him choose between one thing or the other. They are great ice-breaker questions and would help you discover what he likes and what he doesn’t. This sort of question can range from sports to movies and even food. An example of a ‘Would you rather…’ question is, “Would you rather drink only water for the rest of your life or live on only french fries for five years?” You can come up with so many others on your own.

10. Do You Have Favorite People?

Find out more about your date’s social relationships with this question. Through this question, you get to know his relationship with his parents, siblings, grandparents, and those around him. Also, pay rapt attention to how he responds to this question because a great way of determining a person’s character is by hearing the person talk about other people.

11. Do You Have A Favorite Place?

Find out what his safe space is. He might reveal his vacation destination, a cool spot he knows, or even a place where he goes to relax. This is great information that will inform most of your decisions in the future if you decide to continue dating him.

12. What’s The Most Embarrassing Event You’ve Ever Been Through?

Hopefully, the whole conversation has made him comfortable enough to reveal such information. But if you notice hesitation, no matter how slight, quickly let him know it’s okay to not answer and jump right into the next question.

13. What Is Your Favorite Thing To Do On Weekends?

This is just another question that would help you understand what he likes to do to cool off. Hopefully, some of your weekend activities align, which will then lead to you two making other future plans.

14. What Is Your Guilty Pleasure?

Everybody has that one thing they thoroughly enjoy even if it might not be the best thing for them. It could be a snack, a drink, a movie, a TV series, or even a particular activity. With this in mind, asking him this question will help you understand him better.

15. What Is The Thing You Are Most Proud Of?

Most people have specific accomplishments that they are really proud of. Remembering it alone gives them a sense of achievement. It could be something as simple as scoring a desired grade on a particular paper or even being congratulated by your mentor for a job well done on a project. Have him talk about what qualifies as his proudest moment and that would help you understand his values and the things he holds dear.

16. What Helps You Truly Relax When You Are Stressed?

Stress management is a skill that greatly determines the disposition of a person. Whether he is able to manage his stressful moments well or not, it will reflect in his character. Find out how he manages to unwind under stress. Most people decide to take long periods off work while some others only opt for a relaxing bath. Find out what his is.

First Date Questions to Ask the Guy You Like

17. What Makes You Laugh The Most?

If you are nervous or feel the tension increasing between you too, this question will help break the ice. In the process of answering this question, he will remember those things that make him laugh. And a smile is sure to break out on his face.

18. What Is The Scariest Thing You Have Done?

This is one of those questions that reveal the character of the guy you are on a date with. Knowing what scares him and how he was able to go through it regardless reveals certain things you need to know about his character.

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19. If You Were Forced To Eat In A Fast-food Restaurant For The Rest Of Your Life, Which Two Places Would You Choose First?

On the other side of this question, this is a great way to hint at a second date. Hint-dropping is a skill the female gender has mastered with finesse, you no longer have to leave all the work to the guys. Once he tells you his favorite places (and they somehow align with yours), you can subtly hint at meeting up in that spot at a specific time. That’s if you want to, of course.

20. What Is The Thing You Are Most Grateful For?

Ask him what events in his life he is most grateful for. This is a deep question and he would only answer it if he is comfortable speaking to you. If he hesitates, ensure you let him know it is okay to not answer and move to the next question.

21. What Is The Thing You Are Most Afraid Of?

Knowing and understanding a person’s fears is a great step in building any relationship – whether platonic or romantic. It is a deep and very important question. Remember, if he hesitates, move on. It’s the first date, you’re trying to know him better, not be his therapist.

22. What Is The Best Thing In Your Life Right Now?

This is a very personal question, but still, it is a great conversation starter. By answering this question, he would be revealing the things that matter to him most. This would help you understand where his heart is, in case you need to make a decision in the future.

23. If You Could Only Watch A Movie For The Rest Of Your Life, What Would It Be?

Great question. Also a great conversation starter. Hopefully, this could lead to cute movie reviews that would leave you both howling in laughter. Is he more into romantic movies or horror?

24. What Is Your Favorite Social Network?

In this day and age, this has become a very important question. Find out what platform will aid communication and get right in on it.

First Date Questions to Ask the Guy You Like

Since it is the first date, you want to show your interest in getting to know him better, but also, you are not supposed to ask him to divulge his life’s secrets. There is a thin line between being a great conversationalist and crossing a line. These questions are great conversation starters and in some cases, you might only get to ask 2 or 3 of them. But the bottom line is that, at the end of the date, the prospect of a second date must be set in stone!

Do you know any other questions girls could ask the boys they like when they are on a first date? We would love to know what they are, so please share in the comment section.

Keep winning, girl!

All pictures are from Pexels and no attribution is required

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