Breaking the ice with a guy you like can sometimes be challenging. It can also be tough to break past the typical flirty banter and really get to know each other.
I don’t know about you, but nothing is more painful to me (in a not physical pain sort of way) than awkward silences, especially on a date. And talking about the same old things can get tedious.
A little while back I started keeping a list of cool and interesting questions to ask a guy in an attempt to avoid awkward silences and generic conversation. Early on when I started dating my husband, we had a “questions” date night and it really brought us closer and helped us discover things about each other, and ourselves.
And this is something important to keep in mind about conversations in general. Conversations aren’t meant to impress another person, but to discover them. Most people don’t take this approach and that’s why dating can feel so stressful and overwhelming. You can’t just be, instead you try to be what you think the other person wants. The best approach is to go in without an image of them, and without wanting to seem a certain way in their eyes. It’s to see them as a blank pice of paper and see how they fill in the blanks.
MORE: 20 Questions to Ask a Guy to Get Closer
And with that, here is my ultimate list of questions to ask a guy to bond, connect, and just have a laugh! Some are silly and lighthearted, others are deep and serious and will really force him to step out from behind the mask and share his true self… and that is what creates a connection and real intimacy.
I gave a little bit of explanation for the first 50 questions, just to show you why they are such good questions to ask and what they will reveal about a person. For the remainder, I just listed everything out.
All of these questions will open the gates to a deeper connection and bond, something so many people struggle with in this day and age. So enjoy the list, jot down your favorites, and have fun going through them with a guy you like.
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Amazing Questions to Ask a Guy:
1. What’s one thing you always procrastinate on?
This is a really good way to gauge how efficient someone is, and what their priorities are. We all procrastinate on some areas of our lives, and most of us feel guilty about it. The things we just can’t seem to summon the strength to hunker down and get done can be very telling. People who are more floaty types usually procrastinate on practical, day-to-day matters, while Type-A people will procrastinate on mundane tasks that won’t help achieve a goal.
MORE: How to Never Run Out of Things to Say on a Date
2. What is the best way to end a long day?
We all have a happy place we like to go into after a long hard day, and that place says a lot about who we are and what makes us happy.
3. If you inherited a billion dollars, what would you do with your life?
Most of us are confined by our lives to a certain extent. We need to work to pay the bills and we don’t really have a choice. We try to choose a job we’ll like, but not working just isn’t an option. Where we live, where we go, what we wear, what we eat … all of these things are governed by how much money we have. But what if money was no option?
Our lives would look totally different, and we would be totally different. This question will show you what he really values in life. Is he a hedonist who would live a life of pleasure? Or an activist who would pursue change? Or something in the middle?
4. If you could choose one movie character to marry, who would it be?
This is a great question to know what his dream girl looks like, and see how closely you stack up! Granted, no man expects to find a movie character in real life, and if he does then he’s seriously deluded, but it will be interesting to learn what his “ideal woman” would be like.
MORE: 103 Sexy Texts That Turn Him On
5. What is your favorite quote or expression?
What a person remembers and holds onto can tell you a ton about them. Our minds filter through so much information every single day and hold onto a small selection of relevant, important pieces. A person’s favorite quote can be a line that keeps them motivated, something that inspires them, something that reminds them that everything will be OK. No matter what, it will tell you a lot about them.
6. What is always worth the wait?
Delayed gratification is a sign of emotional maturity. What is he willing to wait for and work for?
MORE: 5 Telltale Signs He Likes You
7. Do you believe everything happens for a reason?
Does he believe in destiny or think life is a series of random events? This thought-provoking question will reveal a lot about how he processes the things that happen to him, and will also show what his outlook is in general.
You’ll also learn if he’s an optimist or pessimist, and this tells you how he navigates the world. Does he fall into a pit of despair when things go wrong, or is he able to see the silver lining?
8. How would you describe yourself in three words?
Does this question make him a little bashful, or is he more than willing to share? Does he reveal positives, or are his answers self-deprecating? How we see ourselves can also be a reflection of how we’d like to be seen, so pay attention to this answer.
9. What would you immediately do differently if you knew no one would judge you?
We all hold back for fear of judgment (which is rampant in this day and age of social media!), and to abide by social rules and standards, but what if we could just be? Now there’s an intriguing question…
MORE: 26 Goodnight Texts That Will Melt His Heart
10. What’s one thing you have never been good at?
This is just a fun, lighthearted question. Some of us just suck at things, and it can be fun to bond over them, and laugh about it!
11. What activities make you feel most like yourself?
This is a great question to show who he is … who is his true self and how does he tap into that person?
12. What is your favorite childhood memory?
Anything related to childhood is bound to open up from wellsprings of information! Our childhoods essentially shaped who we are, and those memories are with us for the long haul, both good and bad. This question is sure to bring him to the happiest, most innocent time in his life, a time he probably doesn’t talk about or think about very often, and doesn’t share with many people.
MORE: 10 Signs You’ve Found Your Future Husband
13. Who would you cast to play you in the movie of your life?
This is just a fun question that can show you how realistically, or unrealistically, someone views themselves! Does he cast Brad Pitt or Jonah Hill? He may aim really high, but either way, it’s a fun topic to talk about.
14. If you woke up tomorrow with no fear, what would you do first?
Pretty much all of us are held back by certain fears. Fear of failure, fear of embarrassment, fear of losing money, fear of making the wrong decision. But what would life look like if we let go of all that? The answer can be very telling.
15. What is your strangest pet peeve?
We all have pet peeves, some make sense, some are just silly and totally random. By knowing his, at least you can avoid doing whatever random thing drives him up all wall!
16. If you had to lose one of your five senses, which would you give up?
This may seem like an easy question, but it’s pretty tough when you really think about it and consider the implications. It will also show you what’s most important to him. Does he love music? Does he loves taking in beautiful sights? Is he a foodie who loves delicious tastes and smells? What could he absolutely not live without … and conversely, what would he be willing to give up?
17. If you could make one wish, what would it be?
World peace, or a million dollars? Hmm … which will he choose?
18. What do you consider to be the most difficult period of your life?
This is a pretty personal question, so definitely don’t start with something like this. We’ve all had our rough stages. For most of is, it was middle school and adolescence. For others, it was early adulthood. Or maybe his life was charmed through those typically tumultuous years and he didn’t really start to struggle until later in life. Either way, this question is bound to tell you a lot about him.
19. What is one thing you’re most proud of?
We talk a lot on this site about how every man has a mission… has things he wishes he were achieving. When a woman taps into those things, a man feels incredibly bonded to her and he wants to share himself with her. This questions will show you what means the most to him in life.
20. What is one behavior that makes even the hottest girl instantly unattractive?
This is just a very useful thing to know about a guy you like … lest you accidentally do the very thing he can’t stand!
21. What’s the most embarrassing moment of your life so far?
This will show you how comfortable he is with you so far. If he really likes you, he won’t reveal the most embarrassing, he’ll probably give you something that was mildly embarrassing. Or he might just be a really bold guy with no shame!
22. Finish the sentence: the world would be a much better place if people ___
This is just a fun thing to consider and will show you what traits he considers the most positive and valuable in our society
23. Do you believe in soulmates?
Is he a realist or a romantic? This question is a good way to find out!
24. If you could trade lives with one person for a day, who would it be and why?
This will show you who he admires, and what he hopes his life might look like someday. Who we look up to says a lot about who we are.
25. What is the nicest compliment you’ve ever received?
This question will show you who he wants to be. When we feel good about a compliment, it’s because we want to be a certain way, and the person complimenting us is letting us know we’ve achieved that thing. If you really want to be beautiful and someone says you’re beautiful, you are happy because they are validating the very thing you want. So who does he want to be? And what makes him feel good to hear about himself?
26. Would you rather be happy or successful?
Another great question to find out what he values in life. A type-A goal-oriented type of guy will probably choose success … and this will show you that he will chase success at any cost, even his emotional wellbeing. A more balanced guy who just likes to enjoy life will probably choose happiness. But most people will probably say both!
27. What always makes you smile?
This is a key thing to know about someone you’re dating, or want to be dating!
28. What always makes you angry?
They say alcohol, anger, and how someone handles money tells you the truth about who they are. We have some money questions on this list, and how someone behaves when drunk is really something you’ll have to observe, so now comes anger. What makes him angry? You can use this question to really dig into the topic and get a sense of how easily his angry switch gets flipped.
29. What’s one mistake you will never make again?
Mistakes are what shape us and help us grow. But some are best to never, ever be made again. So what shaped him … and what has he vowed never ever to do again? The answer can reveal a lot.
30. What was the worst part of your childhood?
Childhood is a minefield, so proceed with caution. This question is bound to rouse up some untouched hurts and heavy emotions. Or maybe he had an amazing childhood and really has no complaints. Either way, you will learn a lot about him.
31. When making decisions, do you follow your head or your heart?
The world is divided into thinkers and feelers. It’s not black and white, of course, but all of us predominantly make decisions either with our heads or our hearts. This question will show you which category he’s in and will tell you if he’s a cerebral, practical type of guy, or a sensitive, emotional guy.
32. Does spending time with other people make you feel energized or drained?
This question essentially reveals if he’s an extrovert or an introvert. People often make the mistake of thinking extroverts are outgoing and friendly and introverts are shy and withdrawn, but that’s not actually what distinguishes the two.
What makes a difference is how you feel when interacting with others. Extroverts feel charged up by being around other people, while introvert feels drained after heavy socializing.
33. What’s one thing you do as often as possible to feel alive?
We all have that something that puts us in touch with our essence and reminds us why we were put on this earth. Some people are lucky enough to have a job that allows them to do that thing, like write or paint or dance, other people need to actively carve out time to go to their passion place. Either way, we all have one and it says a lot about who we are, about our core essence.
34. What is something that happened this year that you are most thankful for?
This is a simple, sweet, and telling question. It’s the kind of question that shows genuine interest in someone else and allows them to share something personal and meaningful.
35. If you could re-do one moment in your life, which would it be and why?
Would he leave everything as it happened because that’s what made him who he is today … or maybe there were some mistakes that would have been better left unmade? Now there is an interesting question to think about …
36. What will you never allow someone else to do to you?
Our boundaries are a huge part of who we are. Some people have no boundaries and that’s equally telling of who they are. This question will show you his biggest boundaries, and he may even reveal important events from his past that caused said boundary to develop.
37. How has your sense of right and wrong evolved?
Hopefully, it has developed over time and he doesn’t still operate under the same code of rules that he did as a teenager! We’ve all done things in the past we’re not proud of, we’ve all been wrong and had a hard time admitting it until we grew up and knew better.
38. What would your perfect day look like?
I remember discussing this question with my husband when we were on our third date. I was describing my perfect day and he just looked at me with his mouth wide and said, “That’s my perfect day!” And well, the rest is history!
39. What has been the biggest blessing in disguise in your life?
Life can only be understood looking backward. And in the moment something can feel like the worst thing, but in time it can actually turn out to be the best thing. These kinds of stories are the ones that really shape and define our lives.
40. When was the last time you had a good cry?
Sometimes you just have to let the emotions out, even guys! Men don’t usually openly talk about their painful emotions, so it might be a little uncomfortable for him to share this, but if you can listen without judgment, and without making him feel like a sissy, he will come to care about you even more, and feel closer to you.
41. Do you believe love conquers all?
Is he a romantic idealist or a down to earth realist? This question will tell all.
42. Is there anything you consider absolutely unforgivable?
This is another question that will reveal his boundaries, and as I mentioned, boundaries reveal a lot about a person. Also, when he tells you what he considers to be unforgivable, you can make a mental note never ever to do that thing.
43. What’s something you’re glad you’ll never have to do again?
Most of us have gone through something that totally changed us and made us better in the end. But going through that thing was brutal and painful. We look back and are happy we had that experience, but definitely wouldn’t want to go through that again. So what’s his story? What is the hurdle that he had to overcome to make it to a better place? This question can really take you to some deep and interesting places.
44. What do you wish you could remember more clearly?
This is a deep question most people don’t think about very often. We all have fuzzy memories we wish we could see more clearly, but the information just isn’t there. What are his?
45. What makes you feel accomplished?
This varies wildly from one person to the next. Some people feel accomplished when they get a lot of work done, others feel accomplished from doing errands and other mundane tasks. And others feel accomplished through spending time with others and connecting. The point is, the answer to this question will reveal a lot.
46. What is the biggest lie you’ve ever told?
This will kind of show you if he’s a sociopath or not! Just kidding, but it will be interesting to hear…
47. What do you like most about yourself?
This can often be a tough question for many people to answer because sadly, most of us spend time ruminating over what we don’t like about ourselves, and can’t as easily access what it is we do like about ourselves.
48. What is something you always look forward to?
Concerts? Kisses? Dates? Football season? This question can have a million different answers, all fun to talk about.
49. What keeps you going during really difficult times?
Is it faith? A quote? His family? A positive attitude? How does he keep going when the going gets tough?
50. Where do you hope to see yourself at this time next year?
Now, this is a great question to ask a guy to see how serious and settled he is in life. If you want a committed relationship, then you need to pay attention to this answer. If he says he hopes to be traveling the entire world, he probably isn’t looking to be tied down. But if he hopes to be more established in his career, to have his life more in order, to hopefully be with the right person, then you know you’re on the same page.
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Now here are over 150 additional questions to ask a guy:
What did you want to be when you grew up when you were a little kid?
What is one thing you do now that your younger self would be ashamed of?
Which historical figure would you like to have lunch with?
What is one thing you worried and stressed about that ended up being no big deal?
What is something you wish people would stop talking about already?
What is something you always doubt about yourself?
Which do you prefer: a good book or a good movie?
What is one subject you wish you knew more about?
If you could be fluent in one language, what would it be and why?
What was your favorite toy as a kid?
What was your biggest childhood fear?
What is a random thing that reveals a lot about a person?
What is one book you could read over and over again?
What skill do you wish you could master?
Would you rather have three horrible years followed by the best year of your life or four mediocre years?
What is your biggest irrational fear?
What is something you’re embarrassingly bad at?
What is your most prized possession?
Do you have any feminine qualities?
If you could only eat one food for the rest of your life, what would it be?
What is one thing you never get bored of?
What is your earliest memory?
What is one thing you wish you could remember more clearly?
What topic do you have a lot of useless knowledge in?
Is social media bringing us closer together, or making everyone more isolated and alone?
When was the last time you cried?
What is something that never ends well?
What is one thing you’re judgmental about?
If you had 1 million dollars to donate to a charity of your choice, which would it be and why?
What is something you think should be illegal?
If you had one month to live, what are 5 bucket list items you would do?
What is one thing no one realizes about you?
What are people always surprised to discover about you?
What is your favorite part of the day?
What has been your favorite age so far?
What is something that happened to you that’s so absurd you wouldn’t have believed it if you weren’t there?
If you could go back and re-do one moment in your life, what would it be?
What is your spirit animal?
Do you believe in zodiac signs?
What is one temptation you can never resist?
What is the absolute worst quality a person can have?
Finish the sentence: When the going gets tough, I get _____
Is there anything you’re superstitious about?
Do you think it’s important to keep up with the news?
What is one story you tell that always makes people laugh?
Do you believe in past lives?
What is something that happened in your life that felt like the worst thing at the time, but was really the best thing in the long run?
What is one thing no one will ever know for sure?
What song always takes you back to your teenage years?
When is the last time you laughed so much it hurt?
What is one thing you can never get enough of?
What is one thing that always cheers you up?
What should a healthy relationship provide for the people in it?
If you could only listen to one song for the rest of your life, what would it be?
If you could re-live one year of your life, which would it be and why?
If you could write a note to your younger self, what would you say in three words?
What is one thing that never ends well?
What is one thing you wish you knew as a child?
Which former president would you want to have drinks with?
What would you do differently if you could relive the last three years of your life?
What is an opportunity that came your way that you regret not taking?
What is something that makes you feel like a kid again?
The house is on fire, which three things do you grab?
Have you ever dreamed of being famous?
What is one thing standing in the way of you achieving a goal?
What is your favorite memory?
Who is one person you admire the most?
Did you have a happy childhood?
How would you describe yourself in five words?
What helps you stay positive when everything seems to be going wrong?
What is the best and worst part about being a guy?
What’s your biggest guilty pleasure?
When was the last time you used YOLO as an excuse to do something?
If you had three wishes, what would they be?
Have you ever had your heart broken?
Have you ever broken someone’s heart?
What would your dream job be?
What are you insecure about?
Do you want kids someday?
Do you believe in the paranormal?
What’s your favorite ice cream flavor?
What is your least favorite ice cream flavor?
Do you believe in any conspiracies?
Is all this technology making us smarter or dumber?
How do you deal with people you really dislike?
Do you think some people really have psychic abilities?
What absolutely terrified you as a kid?
What is the scariest movie you have ever seen?
What is the funniest movie you have ever seen?
What is the worst movie you’ve ever seen?
If you could change anything about yourself, what would it be?
Have you ever broken the law?
What is one thing you can’t live without?
Do you enjoy small talk with strangers?
Why do you think the divorce rate is so high these days?
Have you ever been addicted to something?
Are you usually ten minutes late, or ten minutes early?
What is the best prank you’ve ever pulled?
Do you like schedules, or going with the flow?
Do you think it’s better to be honest or kind?
Do you have a mantra you live by?
Do you believe love conquers all?
What is your favorite time of year?
Do you have any recurring dreams? What are they?
Is there anything you wish you could change about your family?
Is there any memory you wish you could erase?
What was the last show you binge-watched?
What is your favorite holiday?
What is the worst lie you ever told your parents?
What emoji best represents you?
What is your proudest accomplishment?
What are you most ashamed of?
Are you a spiritual person?
Do you believe in the afterlife?
Is there a fictional character you identify with?
Are you a suburbs person or a city person?
Do you believe in soul mates?
Have you ever been arrested?
Would you rather be smart or happy?
How old were you when you had your first kiss?
What movie have you seen more times than any other?
Are you a morning person or a night owl?
If you could go on a date with any female celebrity, who would it be?
If you have the power to read someone’s mind who would you choose?
Have you ever cheated on a test?
Have you ever cheated on a significant other?
Have you ever told a big lie and gotten away with it?
Have you ever told a big lie and gotten caught?
What are you most thankful for?
Can you tell me something you’ve never told anyone else?
What is something your parents gave to you that you hope to pass on to your kids?
What is your favorite physical feature?
Who is the one person you go to when you need advice?
What has been your hardest physical challenge?
What has been your hardest mental challenge?
How would you describe me in three words?
What is one place you’re dying to travel to?
What is your favorite memory from college?
Have you ever made a decision that changed the course of your life?
If you had the chance to do it all over again, would you?
What is the most addicting site on the internet?
Do you prefer to stay in on Saturday night or go out?
Have you ever been in love?
What keeps you up at night?
Have you saved any items from your childhood?
Have you ever had a near-death situation?
If you could live anywhere in the world, where would it be?
Do you have any useless skills?
Who is the most overrated historical figure?
Who is the most underrated historical figure?
How well do you cope under pressure?
What three events shaped who you are today?
Have you ever made a huge impulse purchase you now regret?
What do you daydream about?
What food grosses you out?
Do you have any phobias?
What do you refuse to spend money on?
What is something you’re terrible at that you wish you were good at?
What movie always makes you cry?
When was the last time you got really angry?
What is something that really annoys you when other people do it even though you also do it?
Has there been someone who completely changed your life?
What movie do you quote the most often?
What is something that most people don’t appreciate even though they should?
If you could be the best in the world at something, what would it be?
What is something you’ve been wanting to do for a long time but never seem to get around to doing?
What qualities make someone a genuinely decent human being?
What is one topic that always sparks a heated debate between your family?
What was the worst part of high school?
Do you believe in karma?
Is it better to be liked or respected?
What do you consider to be the greatest TV show of all time?
What do you dislike most about dating?
What is the first thing you notice about a woman?
Who was your first crush?
What is your favorite family memory?
What is your favorite family tradition?
If you loved this article, then check out these other must-see related posts:
50 Great Questions to Ask a Guy
How to Talk to a Guy and Make Him Like You
Break the Ice: How to Talk to Girls and Guys
I hope this article gave you some good ideas for questions to ask a guy to really develop a connection. Now I have a question for you. Do you know what inspires a man to commit to a woman? Do you know what makes him see you as a rare gem that he can’t let go of, a woman he wants to be with forever? If not, read this next: The #1 Things Men Desire in a Woman
And now another question. Do you feel like he might be losing interest? Does he seem to be pulling away? If so, you need to read this too: If He’s Pulling Away, Do This...