101 Deep Questions To Ask A Guy You Are Dating

Dating experience | | , Writer
Updated On: April 17, 2024
20 questions to ask a guy you are dating
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You need to always revamp dating with new elements to change things up and keep the spark alive. It could be new types of double dates with friends, adding a dash of romance to your everyday encounters, or even deep questions to ask a guy you are dating to get to know him better.

More often than not, we are so swept up in the glee and excitement of a new relationship that we overlook the core qualities of a person that make them desirable to us. You’re so busy laughing and wiping the ice cream off his face, that you perhaps realize only much later that you may not know him all that well as a person. You know his favorite ice cream flavor and that he’s a clumsy mess but you do not know anything about his past heartbreaks and how they changed him.

Now, dating someone new should obviously not be like some kind of job interview where you ramble off of a list of personal questions to ask a guy to get to know him. But a few pivotal questions and conversations are indeed necessary when you are falling in love with somebody and could even see a long-term future with them someday.

101 Deep Questions To Ask A Guy You Are Dating

Table of Contents

What are some deep questions to ask a guy you just started dating? We’re here to tell you all about it. It takes time to peel somebody’s layers and get closer to them but this list can surely expedite that process for you. Men usually like to hide behind their tough exteriors and don’t give away much, too easily. They prefer to convey their feelings through their actions rather than words and most are ill-at-ease with going all mushy with their emotions.

Once the honeymoon period is over, everything suddenly gets real. You realize that you have landed in a full-fledged boyfriend-girlfriend situation. You can no longer hide behind the infatuation phase. The guy you are dating is now an actual part of your life and you need to get to know and love him for who he truly is.

Knowing the right questions to ask a guy can help you do just that. Don’t make this a rapid-fire round over coffee one day, because you do not want to scare him off. Spread them out over several dates and your man will reveal a whole new side of himself to you! To that end, here are the 101 best questions to ask a guy you are dating to know him better.

Related Reading: 18 Tips To Ace Dating In College

Fun Questions To Know Him Better

There are always conversations that tickle our funny bones or invoke a little excitement. From the most embarrassing moments of life or talking about the most prized possession, here is a set of fun questions to know him better:

1. What’s your favorite party trick?

Most guys have a go-to party trick they use to stand out in the crowd. And they’re usually very proud of it. He will instantly answer this question with great excitement and enthusiasm.

2. Which is your all-time favorite cartoon?

This is definitely one of the most fun questions to ask a guy you are dating. Sharing things like your all-time favorite cartoon shows or movies adds a sense of nostalgia to the conversation. You don’t need to stop at cartoons, you can also ask about his favorite movie, book, fictional character, or childhood memory.

3. Tell me your funniest travel stories

Still, looking for good questions to ask a guy you are dating? Then, definitely use this one. Travels are filled with secrets, stories, and gossip. Each one of these experiences enriches us in different ways. To truly get to know your man better, you need an insight into his travel experiences. Also, imagine all the travel gift ideas you can get from his stories.

4. What is your guilty pleasure?

Such flirty questions are a safe bet, with a hint of fun. He can simply say, “It’s you”, and we know that a part of you is even rooting for that response.

5. What’s the worst date you’ve been on?

Now there are two kinds of dates you can never forget – your best date and your worst date. Add this to your list of good questions to ask a guy you are dating and you won’t regret it.

6. Which is the best one-liner you have used on a girl?

This is one of the good questions to ask a boy to find out how smooth he is with the ladies. And also sneakily check whether he has used his go-to line on you.

7. What song could you listen to on repeat for the rest of your life?

You can ask him to share his all-time favorite songs and listen to them with him. I’m sure he will consider that a truly special moment.

8. Would you rather go to the mountains or the beach?

This is a simpler one in the list of best questions to ask a guy you are dating but will go a long way in helping you plan your travel for two.

9. Who is a celebrity you wish to meet?

Or you could ask about a historical figure as well. The people we idolize or respect tell a lot about the qualities that we admire and aspire to imbibe. This is certainly one of the deep questions to ask a guy. Don’t be jealous if he says Jennifer Aniston, because who wouldn’t!

10. If you were a superhero, what powers would you have?

All of us have wished for superpowers at least once in our lives. Finding out what powers your boyfriend secretly wishes for will certainly give you a unique insight into his mind.

Stories about love and romance

11. What is the best gift and the worst gift you have ever received?

This is one of the intimate questions to get to know someone better. The kind of gifts he appreciates tell you a lot about who he is as a person. Not to mention, make it easier for you to pick out gifts for him. One of the perfect questions to ask on a date night.

12. What song would you sing at a karaoke night?

We all have that one song that we can sing to perfection. Find out what that song is for your boo. Definitely, one of the good questions to ask a boy you’re just getting to know

13. Which fictional villain do you really hate?

If he says Joffrey Baratheon or Cersei Lannister from Game of Thrones, he sure has a good taste.

Related Reading: What You Should Do When Your Partner Flirts With Others At A Party

14. What’s the weirdest phone call you’ve ever gotten?

This is definitely going to be one fun story. That’s what makes it one of the best fun questions to ask a guy on a first date.

15. If you could change your first name, what would be the most epic name you could choose?

Constitutes as small talk but is still a fun question to ask a guy and watch him get creative. You could also come up with adorable pet names for each other

16. What do you always lie about on your resume?

Most people exaggerate a little on their resumes. You could also ask him how is he going to save face if he ever gets caught.

17. What about a woman impresses you instantly?

This can certainly be one of the flirty questions to ask. Just pray his answer doesn’t reveal a misogynistic side to him. If you’ve grown to like him, this can be a bit of a bummer.

18. What about a woman is an immediate turn-off?

It is one of the most interesting questions to ask as well as an important one. You should know what buttons to press and what not to so that you don’t inadvertently end up pushing your guy away.

19. Would you rather go camping or clubbing?

There are two kinds of people, those who like to party and those who like a quiet adventure. Which one is his happy place?

20. If you were stranded on a deserted island for a month, what are the three things that you would take with you?

If he says you, then, I guess, you are the practical one in this relationship.

21. What is your dirtiest fantasy?

This is one of the bolder flirty questions to ask your guy to spice things up. Before you ask it, make sure you’re ready to partake in whatever the fantasy might be or at least open to the idea. Because that conversation is unavoidable after you open this particular can of worms.

Related Reading: Top 10 Hollywood Movies About Cheating In A Relationship

22. Have you ever had an inappropriate crush?

It’s ok if he says his first crush was a school teacher or his mother’s best friend. As long as he draws the line at incest, it’s nothing to be bothered about.

23. Have you ever had the hots for your friend’s girlfriend?

It happens more often than you’d think. After all the heart wants what the heart wants, even if it is the girlfriend of a best friend.

24. What did you think about me when you first saw me?

Definitely, one of the flirty questions to ask your guy. This one can come in handy when you’re looking to be showered with compliments.

25. When was your first kiss?

Won’t blame you for wanting to know how soon he started out and how much practice he’s had. Especially if he is a pro at different types of kisses.

Random Questions That Are Secretly A Big Deal

There are certain questions that don’t seem very consequential when asked, however, their answers help you get to know your guy at a very subconscious level. These random questions to ask a guy hold the clues to what makes your guy tick.

26. Which is your go-to TV/web series?

Everyone these days has their own list of best Netflix series that they’ve either binged-watched over a weekend or have been guilty of repeat-watching. Find out what your guy’s is. There is no better joy than discovering you’re fans of the same shows – it opens up a whole new territory to bond over!

27. What is your favorite food combination?

If your guy is a foodie, you have to ask him this question! If you too are a foodie and on the same page, then you’re going to have a lot of fun exploring food together.

28. What is the craziest thing you’ve ever done?

This is one of the interesting questions to ask a guy. He’s sure to have had this share of crazy adventures that make for the best stories. This is a fun way of getting to know him and his life better.

29. What is your favorite place to hang out?

This is one of the important questions to ask a guy to get to know him deeper because knowing about the little things like his favorite food, favorite place, and preferred hangout is what will make you know and understand him better. Also, the answers to these questions will come in handy in planning surprises for him.

30. What would your gaming room be like?

If there is anything that can beat sex for most guys, it is sports and games. That’s why this is one of the most interesting questions to ask a guy. We bet he will excitedly want to tell you more about it. He’s going to love that he has a gamer nerd girlfriend!

best questions to ask a guy you are dating
Know about his gaming interests and join the fun!

31. What is the worst tattoo you’ve ever seen?

Many guys have a thing for tattoos and have a fair knowledge about them as well. Asking him about something like this can keep him engaged in the conversation. If your relationship has reached that level, maybe you could get matching couple tattoos. The least you can do is compare your worst tattoo stories and have a good laugh about it.

32. What is your biggest pet peeve?

We have already covered what it is that turns him on. Time to flip the coin and get to know what his pet peeves are and what are the things he considers annoying or silly.

33. Who is your hero?

It could be a historical figure or his mother or someone who saved his teddy bear from getting torn to shreds. But that person will surely be special to him.

34. Do you like or dislike surprises?

Some people like spontaneity and some like planning out the smallest details. So which kind is he?

35. What household chores do you hate the most?

This is not one of the flirty questions to ask, but you will now know what chores will he try to get out of if you ever move in together.

36. If you were granted three wishes right now, what would you wish for?

This is one of the deep questions to ask a guy that will actually give you a little insight into what is important to him. Let’s hope he doesn’t respond with “three more wishes” because that’s just boring.

37. If you are in a bad mood, do you prefer to be left alone or do you want someone to cheer you up?

Everyday life has its ups and downs. And there is nothing more annoying than a person not leaving you alone when you just want some time to gather yourself after a long day. Deep questions to ask a guy such as this will help you understand how best to respond when your boo is having a bad day.

38. Are you friends with your exes?

There are some unspoken boundaries for being friends with an ex and as long as your guy honors these, his relationship with his former partners shouldn’t be an issue. However, if you believe that being friends with an ex is never a good idea, then this issue can become a bone of contention between you two.

39. What gross and unhygienic things do people do that bug you?

Maybe it’s biting your nails or wiping your hands on your jeans. It is best to find out early on.

40. What do people really need to chill out about?

And get his honest opinion about today’s cancel culture.

41. What would you do if you found out you were the star of the Truman Show?

If he has not seen the movie, then you could always turn the date into a movie night. Who knew this would turn into flirty questions to ask a guy?

42. What is a waste of money according to you?

How you spend money says a lot about you. That’s why this is one of the deep questions to ask a guy that you just cannot miss out on if you want to understand his relationship with money and how it can impact your relationship with him.

43. If you could teach every girl on the planet one lesson about men, what would it be?

This is one of the deep questions to ask a guy that can reveal a lot about his worldview. Also, take notes.

44. Have you ever ghosted a girl?

Ghosting in a relationship is never okay. However, most of us are guilty of having done that to someone or the other. Is your guy too guilty of it? If so, what were the circumstances that led me to dump someone so unceremoniously?

45. What is the weirdest thing you have done to get someone’s attention?

There is no one in the entire world who has not done something silly in love at least once in their life. Such cringeworthy moments make for great stories. So, go ahead and ask this question to discover a side to him that he may have kept neatly tucked away so far.

46. If you could, would you rather choose a girl with lots of money or a girl with lots of love?

Love is important and so is money. Which one will he choose? The answer can tell you a lot about his priorities in life and whether they align with yours.

47. How would you react to someone hitting on me?

Being a little protective is sometimes sweet. But if he gets easily jealous, then it might be a red flag.

48. Have you ever ignored my text? Why did you do it?

This question is a minefield. Any answer apart from no might blow him up to smithereens. So, if you decide to ask a guy such questions, make sure you’re prepared to deal with whatever his answer is.   

49. Would you rather choose a calm and stable relationship or a hot and wild one?

To each their own, I guess. But this is one of the important questions to ask a guy to assess whether you’re on the same page about what a relationship must look like.

questions to ask the guy you are dating
Know what kind of music he loves

50. Have you ever had sex in a public place?

Sex in a public place can be fun for who those who find the possibility of getting caught in the act exciting. Maybe it’s something your guy is into. Ask and ye shall find out. And if you too feel the same way, well, you now have another way to spice up your sex life.

Serious Questions To Ask A Guy

Some people fall in love at first sight, and some fall in love at the first conversation. And some look for zodiac compatibility. While falling in love can be an instant experience, staying in love needs consistent work from both partners and a strong connection that is constantly nurtured with love and attention. These serious questions to ask a guy will build a deeper connection, which is the foundation of healthy relationships.

51. Who is the person you turn to when you think you have no one?

This is a deep question to ask a man because you’ll get to know who else he considers truly special and close to his heart. Make this one of the important questions to ask the guy you’re dating, so you can ensure you too have a good relationship with the people he loves and trusts.

52. What is your biggest regret?

This is one of the best questions to ask a guy you are dating. It will help foster vulnerability and deeper emotional intimacy in your relationship.

53. Where do you see yourself in 5 years?

With a new guy in your life, it’s important to gauge and get an idea of what’s on the horizon for the two of you as a couple. Your goals don’t have to be the same, but they should intersect. That’s what makes this one of the important questions to ask a guy you’re dating.

54. Do you believe in marriage?

This is both a serious and flirty question to ask. Marriage is not something that everyone believes in. Thus, if you are somebody who is serious about marriage and settling down, it can be helpful to know how your boyfriend feels about it.

55. What’s your most controversial opinion?

This is one of the common and well-known online dating questions to ask him. No, we don’t mean for you guys to start a debate but having something thought-provoking to talk about is always good for your relationship.

56.  What motivates you to work hard?

Each of us has days when we don’t have the strength to get out of bed. It’s good to know what keeps your guy going on those days.

57. If there was anything in your life you could re-do, what would it be?

There is not one person on the planet who doesn’t have regrets. That’s precisely why this is one of the serious questions to ask a guy to get to know him on a deeper level. Maybe you could help him feel better.

58. Do you believe in God?

A person’s concept of a higher power is an important and intimate question to ask to get to know someone. Especially if spirituality is important to either one of you.

59. Do you believe in love at first sight?

There are two kinds of people, those who believe in love at first sight and those who don’t. Which one is your guy?

60.  Would you rather win the lottery or work at your dream job? Why?

While winning a lottery does feel good, for many people, it lacks a sense of fulfillment. On the other hand, a dream job can put you on a career path that will keep you happy almost forever. What is your man’s take on this? It can be an interesting discovery about his character, goals, and ambitions.  

61. What are your top 3 favorite animals and why?

How he describes the qualities of the 1st animal is how he sees himself, the 2nd is how the world sees him, and the 3rd is what he truly is. Hard to believe but deep questions to ask a guy such as these can offer a lot of insight.

62. If you had all the resources that you needed, what would you do?

Watch his face light up as he explains what he has always wanted to do. This is one of the questions to ask a guy to get to know him deeper.

63. What do you think of best friends of the opposite sex?

If either of you thinks a man and a woman cannot be just friends, then this is one conversation you should have.

64. Does your job make you happy?

Unfortunately, a lot of people are in their current job because it affords them their lifestyle. However, being in a job that makes you happy is a whole different level of satisfaction. Is your guy lucky enough to experience it?

Related Reading: 50 Best Speed Dating Questions To Start A Conversation

65. What is a relationship deal breaker for you?

It is very important to know your partner’s relationship deal-breakers before you get into a relationship with them so that you can make an effort to avoid doing things that could jeopardize your entire relationship.

66. What’s the one thing people always misunderstand about you?

Even our closest people tend to misunderstand us once in a while. What’s the one thing you man feels misunderstood about? Ask this question and give him a chance to lay his heart bare to you.

67. What are the two biggest lessons you have learnt from all your past relationships?

Relationships have the power to change us. We don’t come out of a relationship as the same person that went in. Every relationship teaches us something, and being aware of that is a sign of self-awareness.

68.  What do you consider a wasted life?

Everyone’s purpose in life is unique. Ask him this question to get to know him deeper.

69. How big of a deal are special occasions for you?

Mostly women are accused of obsessing over dates, but sometimes men do it too. Better find out before you miss a special occasion and disappoint him. On the other hand, if he doesn’t like to make a fuss about special days, at least you’d know it’s best to keep things low-key.

how well do you know your partner quiz

70. Have you ever cried because of me?

If he says yes, this is the perfect opportunity to make things right and help him feel better.

71. Do you let your friend’s opinions get in the way of your relationship?

Friends are the family we choose, so it is understandable that their opinions matter. However, it is important they don’t run your life for you.

72. Do you think you could be in a long-distance relationship?

Long distance is not everyone’s cup of tea and if there is a possibility of it in the near future, then it is better to talk this out and make a plan.

73. What is the best part of being in a relationship?

This is one of the most flirty questions to ask. For some, it is companionship and cuddles, and for others, it is the feeling of loving and being loved. What is it for your guy?

74. Do you think it is okay to keep secrets in a relationship?

Does your partner equate secrets to cheating or lying? Sometimes you need to draw a line between love and privacy. It is something you should talk about early on in your relationship.

75. Is there something you have done in the past that you can’t forgive yourself for?

He may or may not want to talk about it. If he doesn’t, don’t push him. If he does, let him know that you’re there for him.

Intimate Questions To Ask A Guy

All of us have a side to our life and personality that we share with only the most special people. If a guy answers these questions for you, then it is a sign that your man considers you as his special someone.

76. Have you ever been heartbroken?

His first breakup or his first love is likely to have impacted him in a big way. He could share his heartbreak story if he is ready to let you into the deepest recesses of his heart because he may not be comfortable opening up like this to everybody.

77. What is the weirdest habit you have?

Maybe he likes to dip his omelet in tea. Or put ketchup on his pancakes. Whatever it is, try not to judge him (not blatantly anyway).

78. What is it that instantly turns you on?

There will be instances when you will have to turn up the heat a little. Having some knowledge about what makes your man tick will definitely help you go a long way. Certainly, one of the flirty questions to ask your man.

79. What is the one rule you hated to follow but had to follow anyway?

On the side of more fun questions to ask a guy you are dating. The rule can be a family tradition or a disciplinary rule at school that he had to follow. It is sure to bring up some interesting stories that will give you a glimpse into his life before you.

80. Have you ever broken someone else’s heart?

A truly self-aware guy will go one step ahead and tell you much deeper truths about his past relationships. It’s possible that you’ll open a can of worms though, so ask this question only when you are ready to hear whatever the answer may be.

Related Reading: 25 Questions To Ask Before Marriage To Be Set For The Future

81. What is your biggest fear?

Public speaking, snakes, water, or just clowns – you should definitely know what are the things that make your boyfriend frightened or uncomfortable. The sooner you know them well, the better girlfriend you will be.

82. Do you see a future with me?

Important questions to ask the guy you’re dating and a disaster if he blurts “no” in response to this question. To really get an idea of whether he loves you or is lusting after you, pop this question so you can adjust your expectations and feelings accordingly.

83. If you have the power to stop time for 24 hours, what would you do in it?

This is one of those questions to ask a guy to bring out his creative juices. Also perfect as one of the online dating questions to ask him. He could talk about robbing a bank or living in the most luxurious house. You could add to his imagination and make it into something more sensual and sexy.

84. If you died today, what would your greatest achievement be?

One of the personal questions to ask a guy. He will be thinking long and deep about this one. His answer could be funny, sarcastic or even philosophical, depending on the kind of person he is.

85. What is your biggest complaint about your job?

Even if it is a dream job, you do hate it sometimes……

86. What was the worst phase in your life?

Struggles maketh a man, sometime man maketh the struggle. One of the deep questions to ask a guy that will help you understand him better.

87. What qualities do you admire in your parents?

Family values are very important. They play a major role in a person’s personality in the future. The qualities that he admires in his parents are the ones he will try to imbibe if and when he becomes a father.

88. Which parent are you closer to?

It’s a well-known secret that parents have a favorite child. Children also have a favorite parent. It’s quite fair really…

89. Would you ever take back someone who cheated?

Sometimes it is easy to forgive but difficult to forget. Ask your man’s views on infidelity so that you know where he draws the line in the sand.

important questions to ask the guy you're dating
Make sure you know well who is in his close circle and who he trusts

90. Who is that one person you can talk to just about anything?

Be prepared that person may not be you, but it is also the person whose opinion matters the most to him.

Related Reading: 33 Questions To Ask Your Significant Other To Know Them Better

91. What would you do if your parents didn’t like your partner?

Now, this is one of the interesting questions to get to know him deeper. Family members are important and you will find out exactly how important they are to him.

92. What is a life lesson you had to learn the hard way?

That’s the thing about life lessons, you usually learn them the hard way.

93. What is your opinion on having children?

This is an important question to ask a boy. If you are planning to have kids of your own someday, then you must have this conversation before marriage or before you become to invested in the relationship

94. What is the most sensitive part of your body?

The answer could surprise you. That’s why it is so important to ask such questions to foster deeper intimacy in the relationship. Not to mention, you can use this knowledge to your advantage in the bedroom.

95. What is something that is completely off-limits in the bedroom?

Consent is queen. And such conversations go a long way in helping you understand your partner’s sexual boundaries.

96. How are we positively affecting each other’s life?

Deep questions to ask a guy, like this one, are worth a million dollars if you want to know what you mean to him.

97. What is one thing you took for granted in your last relationship?

Knowing where you went wrong and admitting it is an important component of being self-aware. If your man is self-aware, he is going to make a conscious effort to improve his relationship with you – and that’s quite an admirable quality to have.

98 What is the biggest doubt you have about me in this relationship?

Every relationship has these moments of insecurity. It might disturb his comfort zone a bit, but it is best to clear things out as soon as possible.

99. Do you still have feelings for someone in your past?

This is certainly one of the deep questions to ask a guy. It is difficult to get over someone you love. However, he should’ve gotten closure before he started dating someone else. If he says yes to the question above, then you better run.

100. What is the best thing you have done just because you were told you couldn’t?

We all love a little rebellious streak and this one story is sure to let you know how much of a badass he is.

Bonus Question

101. What is the darkest thought you ever had?

It takes a lot of strength to be this vulnerable to someone. If he does answer this question, then it is a good sign for your relationship.

Getting to know your new boyfriend is very important because when things get serious and it is time for you to put both feet in, you need to know him inside out. Ask him the right questions without being too clingy to make sure you truly know the man you’re with. Falling in love is beautiful but it’s better to act with caution and get to know your partner well. Enjoy your relationship, go with the flow, have fun and make the most of it!

The article has been updated in October, 2022.

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