The expression ‘first impression is the last impression’ terrifies any girl who just got lucky to go on a date with her dream guy as she doesn’t want to mess it up by appearing too intriguing but at the same time has several questions bombarding in her head to ask to learn more about her potential future life partner.

It takes a great deal of talent to pose right, interesting and engaging questions to extract intact information from the prospect without making him lose his interest in the conversation. Asking question is an art, a skill that every girl must master. Ask questions in a way that you sound genuinely interested in him.

Are you one of those blessed ones who just got a date with your prince charming? Are you racking your brain contemplating what to ask and how to ask? Relax! Here is a list of carefully crafted mix of serious and interesting questions you can pose without running the risk of upsetting him accidentally. There is barely any guy who is not interested in sports, so embark on your question bank with sports, gradually taking it down to more personal ones.

28 Questions To Ask a Guy:

1. Which is your favorite sport? Which is your favorite team and who is your favorite player?

Your objective is to learn more about his personality and his approach in life while engaging him in interesting conversation. Guys can speak endlessly on ‘sports’ so, touch the right chord but be shrewd enough to navigate him towards other questions you have in mind.

2. Do you yourself play any sport?

Ask this question to boost his enthusiastic participation and to learn if he is boisterous or likes engaging in calm games.

3. What do you do when you witness a foul play from one of your teammates?

His answer will reveal if he is generally fair in life towards others or not.

4. Which is your fond memory?

This question may make him candid and he may open more pages of his life you can have a peek into.

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

It’s one question that gives room to many more interrelated questions thereby providing you ample opportunity to know who he really is.

6. Do you like to socialize or mostly prefer ‘me time’?

It’s basically to learn if he is a party animal or a loner. If you enjoy being surrounded by friends and people, you would like your guy too to be same.

7. Where did you spend your childhood?

It will tell you about his past and where he comes from. It’s imperative to know the past of a person to understand him better.

8. Which school did you go to?

You will learn about his foundation and what to expect from him.

9. Which is that one superpower you would like to possess?

You can ask it just for fun but it will also give an insight about his secret desire. You may also ask why he would like to have that particular super power.

10. Are you an introvert, extrovert or an ambivert?

Pose this question to learn about his personality. If he says introvert, be prepared to be a bit more astute in grilling him for answers.

11. What is that one quality you admire in your fast friend? Do you share everything with him/her?

Any quality he mentions, you can be assured that he too has the same or he can get along with you well if you too share the same quality. Even if you don’t have, you can work on it if you really want to be with him.

12. What do you value the most in your friends?

A man is known by the company he keeps. His reply is directly proportional to what he is. Everything he says, is what you can expect to explore in him as a companion.

13. What are the qualities of a person you dislike the most?

It’s a direct probe into his nature.

14. Who is your role model?

Learn about his aspirations.

15. Are you a vegetarian or non-vegetarian? What is your favorite food?

Yes, you know it. Way to a man’s heart is through his stomach. You can tickle his taste bud and he will be all praises for you.

16. Do you enjoy travelling? Which is your dream destination?

This question directly translates in learning about his approach in real life scenarios. An explorer has a strong appetite for challenges and risks and has the ability to wade through tough times with courage.

17. What is your unfulfilled wish list you would like to fulfill?

You may secretly plan to unite him with some of his wishes. Believe me, even if you both don’t end up together, you will still cherish that moment for life.

18. Do you like pets?

If he is an animal lover, you can safely assume that he will never hurt anyone intentionally and that he values life.

19. Which is your worst nightmare?

It’s good to learn about a person’s fears along with his strengths.

20. Do you believe in superstition? Are you superstitious?

It reveals if he is an orthodox or an open- minded guy.

21. What is your career goal?

Well! You obviously want to know if he is ambitious or not.

22. What are your hobbies?

Hobbies tell a great deal about a person’s personality and nature. If you both share same hobby, then nothing like it.

23. When and what was the most embarrassing moment for you?

Its intended for fun but if he is still skeptical about it then make sure you say nice things to him.

24. What are you passionate about?

Passion doesn’t always translate into profession for all. His passion is what he really enjoys indulging into.

25. Do you have siblings? Who are you close to in your family?

It is good to know about his family. His siblings may become your lifelong friends so, plan with him to meet them after you both start gelling well.

26. Do you like to play pranks on others? Which was the naughtiest prank you ever did?

Learn if child within him his still alive.

27. If you spot an unknown damsel in distress and at the same time your best friend needs you desperately, who would you reach to and why?

Ask it only for fun, just to pull his leg. It will also send a message that you are naughty and bubbly too.

28. Will you believe me if I say I really like you and would like to meet you often? Will you meet me tomorrow?

Club this question with a naughty smile at the end of your meeting to know if he is interested in you or not. If he says yes, then that’s your eureka moment. You can dance inside but play calm outside.

Hope you are feeling much more confident to date him after reading this article. These are few questions that can come to your aid. You may add some more open-ended questions for more interaction. Just remember to play your emoticons along when he answers your questions. Exclaim and get surprised at precise moment. Wait for his pregnant pause to add your thoughts.


Anna Perkins is a relationship writer who offers her own forthright opinion over the worlds of dating, romance, relationships , marriage and friendships. She loves cats, traveling, spending time with her son and husband.

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