207 questions to ask a guy that’ll bring you much closer

If you’ve been in a relationship with your boyfriend for a while and are looking to learn more about him to help you decide if he’s the one for you, asking lots of questions can either prove informative or annoying – so approach with caution.

Rather than just grilling him with all kinds of questions to ask a guy, try approaching with some classic questions that will make him feel comfortable and open up a bit more.

Getting to Know People is Harder These Days

Despite having a great deal of access to people through technology, it is actually harder to get to know someone now because we are all so distracted by the same technology that is supposed to bring us closer.

In order to connect with guys on a deeper level, sometimes you have to put in more of an effort, and asking these questions to a guy is a great way to get the information you want to help you decide if he’s the right guy for you.

Questions to Ask a Guy to Get to the Root of His Thoughts

There is no right or wrong way to ask questions of people. However, there are a few things you can do to make the most of those questions to get the information you want.

Whether or not he says things that you want to hear is another story, but you can certainly work your questions to learn as much as possible.

Don’t just ask a question; be sure to ask follow up questions to make the most of your conversations.

Once you go through these, you’ll be best friends before you know it!

The First 17 Questions You Must Ask a Guy and Why

1) What do you wake up excited about?

This is not only a great conversation starter and way to show someone you’re interested in them, but a perfect way to find out what they’re passionate about.

2) What is your unusual hidden talent?

An entertaining way to find out how much someone is willing to share about themselves, and if you make it to a first date, asking for proof is another great icebreaker.

3) How do you spend a typical Saturday night?

How someone spends their night off is a great way to learn what their priorities are.
Whether they’re a party animal or workhorse, your lifestyle and tastes will determine if they give the ‘right’ answer.

4) What struck you about my profile?

This provides more insight into their intentions. A specific, thoughtful answer suggests that they’re interested in really getting to know you, a generic copy/paste answer is a clue that they’re just looking for a fun time.

5) What accomplishment are you most proud of?

Encouraging someone to talk themselves up a little bit not only lets you learn more about them but shows them you’re someone who lifts others up and are worth meeting.

6) What are your thoughts on religion?

While it might be a touchy subject for some, it can also let you know if your values align. Which will become important if you hit things off.

7) Where did you study? Why did you choose that school?

Asking how someone made a major decision like where to attend school, gives you a peek into their decision-making process, and where their priorities lie.

8) “Would you rather…” questions.

Questions like, “would you rather jump out of a plane or swim with sharks?” are a fun way of breaking the ice, sharing some stories, and really getting to know someone.

9) What’s your most embarrassing story?

Not taking yourself too seriously is attractive. Embarrassing stories are hilarious. Sharing stories with a sense of humour is fun. This question is a gold mine.

10) How often do you see your family? Where do they live?

This is a great way of gauging what their family values are and if they line up with yours. If you hit it off, this is something that will become important.

11) What cause are you most passionate about?

Their enthusiasm for the topic will shine through in their words, and you get to learn all about something that is truly special to them.

12) What are your interests?

On the same theme, but with a slight variance from the passion question above it’s a great way to learn more about someone. An interest in boatbuilding might mean a trip to the museum from time to time, a passion for it might result in hours bent over a replica ship in a bottle.

13) Describe your go-to drink?

Hopefully you’ll take this conversation offline and in person, it’s nice to know if you’ll be splitting a pitcher, sipping on wine, or cheersing with cola.

14) What are your favourite books, TV shows, or movies? Why?

A classic question, and a great conversation starter. You may find that your love of Game of Thrones brings you together, or get some great new recommendations.

15) Who’s your greatest role model?

Whether they describe a historical figure or a family member, you’ll learn something about their character by the people they hope to emulate.

16) Describe your dream vacation.

This not only gives them a chance to share stories from previous vacations but lets you know if your vacation styles will match up should you hit it off and start planning trips together.

17) What’s the best way to earn somebody’s respect?

An eye opening question that explains what they actually value in themselves and others. Do they admire kindness? Or do they give their respect to work hard?

40 Essential Questions and Follow-up Questions

Here is a list of 40 questions to ask a guy and we’ve thrown in some possible follow-up questions to help you get more out of your conversations.

What has been your proudest moment of your life?

1) What made it so special?

2) What is the funniest thing you’ve ever witnesses?

3) What made it so funny?

4) How do you like to veg out?

5) What’s your favorite Netflix binge show?

6) What is the scariest thing you’ve been through?

7) Did you change anything about your life afterwards?

8) What’s your best memory from growing up?

9) What was your favorite toy?

10) When was the last time you did something nice for someone?

11) What prompted you to do that for that person?

12) What makes life worth living for you?

13) Why is that important to you?

14) What is your favorite kind of animal?

15) What animal would you be?

16) What’s your go-to favorite movie?

17) What makes it your favorite?

18) What’s one thing you have never told anyone?

19) Why haven’t you told anyone that?

20) What are you afraid of in life?

21) Do you think that stems from a previous experience?

22) If you had to leave your house, what is the one thing you couldn’t leave without?

23) What would you definitely leave behind?

24) Who’s your favorite family member?

25) Who’s your least favorite family member?

26) What’s Thanksgiving dinner like in your family?

27) What do you eat at Thanksgiving?

28) What’s the best worst joke you’ve ever heard?

29) Who told it to you?

30) What is your favorite kind of ice cream?

31) What kind of toppings do you like?

32) What do you like about yourself?

33) Why do you like that about yourself?

34) What’s one thing you would change about your life if you could?

35) Have you ever thought about how you might go about making that change?

36) What’s one thing you wouldn’t change about your life?

37) Why is that so special to you?

38) If you had to eat the same food for a month, what would it be?

39) What would be for dessert?

40) What’s your favorite drink and why?

50 questions to ask a guy that will reveal his true personality

1) Which fictional character would you marry if you had the chance?

2) Where would you live if money and work were not factors?

3) What was the worst book you’ve ever read?

4) What was the best book you’ve ever read?

5) Who is your favourite Avenger?

6) Batman or Superman: Who is your favourite DC character?

7) What are the three words you would use to describe yourself in an online dating profile?

8) Do you prefer to listen to your heart or your brain when making important life decisions?

9) Would you say you are a spiritual person?

10) Who is one person you wish you could be?

11) Who is someone you looked up to when you were a kid?

12) Do you ask permission or ask for forgiveness?

13) What is the best advice you would give someone?

14) What is the best advice you ever got from someone in your life?

15) What is your biggest pet peeve and when was the last time someone did it around you?

16) Who is your dream woman, dead or alive?

17) What fictional character do you think you are most like?

18) Who would play you in a movie about your life?

19) How much money do you wish you could make at your job?

20) What would you do for a living if you could do anything?

21) What is the best advice your mom ever gave you?

22) What is the worst movie you’ve ever seen?

23) What movie do you wish you could have starred in?

24) What fictional lawyer would you want representing you if you ever got in trouble with the law?

25) Do you keep up with current events?

26) What do you think is the most significant event in our human history?

27) Do you think BigFoot is real?

28) Would you ever climb Mount Everest?

29) What is one thing on your bucket list?

30) Who is on your fantasy football team?

31) Would you rather be smart or handsome?

32) Do you like hot dogs or hamburgers?

33) If you could only eat one food for the rest of your life, what would it be?

34) If you could work for any company, what company would it be?

35) What movie have you watched that left you wishing you did that for a living?

36) Would you swim with sharks?

37) If you could have a superpower, what would it be and why?

38) Would you ever quit your job to live in the woods?

39) What is the worst job you ever had?

40) What is one thing you regret not doing in your life?

41) What is your favourite television show, now or in the past?

42) Have you ever had an idea for a movie of your own?

43) Have you ever tried to write a book?

44) What’s the funniest thing that has ever happened to you?

45) What do you wish people didn’t know about you?

46)What is your favourite music or song to listen to?

47) If you had to listen to one song on repeat forever, what song would it be?

48) Do you believe in love at first sight?

49) Do you believe in reincarnation?

50) Have you ever experienced Deja Vu?

RELATED: My love life was a train wreck until I discovered this one “secret” about men

30 funny questions to ask a guy

Humor can help you go a long way with a guy. Men like having a laugh because it lightens the mood and makes them feel happy.

So if you think you’re funny then this can be a good chance to make a good impression on your man.

Make him realize that you can make him laugh and chuckle.

Here some funny questions to lighten the mood:

1) If you were a girl for a day, what would you do?

2) What’s the weirdest celebrity crush you’ve ever had?

3) Do you think nerds are sexy?

4) If you were a vegetable, what would you be and why?

5) If you could have one superpower, what would it be?

6) What would you do if we were in zero gravity?

7) What would your dream mansion look like?

8) What’s the weirdest conversation you’ve ever overheard?

9) What is something you believe that most people don’t?

10) What’s something you can’t believe people actually enjoy?

11) What’s the funniest screw up you’ve ever seen on social media?

12) Who do you think is the hottest celebrity?

13) What would you do if a guy asked for your number?

14) Do you think older women are sexy?

15) What kind of ice cream describes you best?

16) If your live was a movie, what would it be called?

17) Would you still like a girl if she was a foot taller than you?

18) What alcoholic drink best describes your personality?

19) If you could make out with any fictional cartoon character, who would it be?

20) If someone had something on their face, would you tell them?

21) If you owned a boat, what would you call it?

22) Which celebrity would be most boring to meet?

23) What’s the worst purchase you’ve ever made?

24) Best purchase?

25) If you could choose your name, what would it be?

26) What’s a compliment you’ve received that was actually an insult?

27) If you had to lose one body part, what would it be?

28) Do you believe in magic? Why?

29) What’s a famous quote that everyone takes as truth but is actually bs?

30) What’s the funniest viral video you’ve ever seen?

30 personal questions that will bare his soul to you

Let’s get one thing straight:

You can’t have small-talk all the time. It’s boring, lacks meaning and no spark will be ignited.

Sometimes you need to go a little deeper.

One way to do that is through personal questions.

So here are some questions to get to know someone for who they truly are:

1) What were the happiest moments of your childhood?

2) What does your perfect relationship look like?

3) What’s the main reason you get out of bed every day?

4) What do you enjoy most doing?

5) What’s your number one goal right now?

6) If you were going to die in one hour, what would you do?

7) What book has impacted you most in life?

8) If you could send a message to the world and they would listen, what would you send?

9) Is there anything you’re extremely self-conscious about?

9) What’s the most challenging thing about life right now?

10) Are you an adventurous person? Or do you prefer routine?

11) What’s the closest relationship you’ve ever had?

12) What is something you’re certain you’ll NEVER do?

13) What stereotype describes you best?

14) What’s your best trait?

15) What’s your worst trait?

16) What’s the worst advice you’ve ever received?

17) Who couldn’t you live without?

18) What sparks your light and gets you motivated?

19) If you could go back 10 years, what would you tell yourself?

20) Do you say yes or no more often in life?

21) What you rather go to an art, history, or science museum?

22) What did you take as truth when you were growing up, but now you know is wrong?

23) When was the last time you panicked?

24) What was the weirdest conversation you’ve ever had with someone?

25) What’s a personality trait of yours that you wish you could get rid of?

26) What do you think of homeless people begging for money?

27) What is your favorite scene ever in a movie?

28) What’s an opinion you have that isn’t mainstream?

29) What stresses you out?

30) Would your rather be a famous actor or sportsman?

20 romantic questions to ask him

Eventually you probably want to connect on a more romantic level. After all, romance is a beautiful thing.

So if you’re looking more romance, check out these questions to ask:

1) What is your dream romantic date like?

2) What song makes you think about me?

3) What is the most romantic act you’ve ever heard of?

4) Have you been in love before?

5) Do you think you could fall in love with me?

6) What nickname/pet name would you call me lovingly by?

7) Do you think someone can be too much in love?

8) Which trait of mine first drew you to me?

9) What was your first-impression of me?

10) What’s something about your life that you’ve never share with anyone?

11) How did you feel when we had our first kiss?

12) Do you prefer good sex or a good hug?

13) Do you think you’ll ever want to settle down and have kids?

14) What’s the most romantic movie you’ve ever seen?

15) What’s the number one best thing about being in a relationship?

16) What memories between us do you cherish most?

17) Is communication more important than sex in a relationship?

18) Do you want to have a big wedding? Or a small one?

19) What’s the sexiest dream you’ve ever had?

20) Guess what I like about you most.

Deep questions to ask

Once you’ve established a connection, it’s time to go deeper. You want to know their perspectives on life.

Ask these questions to get to know how their brain works:

1) What or who would you sacrifice your life for?

2) What’s something you believe that most people don’t?

3) If money wasn’t an issue, what would you do in life?

4) What keeps you up at night?

5) How important is physical attraction in a relationship?

6) What issue in politics do you wish got more attention?

7) What do you wish people didn’t know about you?

8) What three words describe you best?

9) How do you want to be remembered?

10) What is the best advice you’ve ever received?

11) Why are so many people lonely these days?

12) Do you believe in fate?

13) Karma?

14) Are you proud to be part of the human race?

15) How important is money to living a good life?

16) What makes life worth living?

17) Can you tell things about a person from the way they look?

18) What was the last book you read?

19) What movie changed your perspective on life?

20) What’s your favorite motto in life?

These questions are great, but…

Regardless of where you are in your relationship, asking questions of one another is a great way to get to know someone and to keep tabs on where you are both at in life.

Even when you’ve been with your guy for a long time, you can continue to build a close relationship with them by staying curious about their likes and dislikes, and check in once in a while to see if things have changed for your guy.

Communication is an important part of a healthy relationship. However, I don’t think it’s always a deal breaker when it comes to the success of one.

In my experience, the missing link in a relationship is failing to understand what your guy is thinking at a deep level.

Because men see the world differently to you and we want different things from a relationship.

Not knowing what men need can make a passionate and long lasting relationship —  something that men crave just as much as women — really difficult to achieve.

While getting your guy to open up and tell you what he’s thinking can feel like an impossible task… there’s a new way to understand what’s driving him.

Men need this one thing

James Bauer is one of the world’s leading relationship experts.

And in his new video, he reveals a new concept which brilliantly explains what really drives men. He calls it the hero instinct.

Simply put, men want to be your hero. Not necessarily an action hero like Thor, but he does want to step up to the plate for the woman in his life and be appreciated for his efforts.

The hero instinct is probably the best kept secret in relationship psychology. And I think it holds the key to a man’s love and devotion for life.

You can watch the video here.

My friend and Hack Spirit writer Pearl Nash was the person who first mentioned the hero instinct to me. Since then I’ve written extensively about the concept on Hack Spirit.

For many women, learning about the hero instinct was their “aha moment”. It was for Pearl Nash. You can read her personal story here about how triggering the hero instinct helped her turn around a lifetime of relationship failure.

Here’s a link to James Bauer’s free video again. He provides a terrific overview of the hero instinct, and gives several free tips to trigger it in your man.


Disclosure: This post is brought to you by the Hack Spirit review team. In our reviews, Hack Spirit highlights products and services that you might find interesting. If you buy them, we receive a small commission from that sale. However, we only ever recommend products that we have personally investigated and truly feel could be valuable to you. Read our affiliate disclosure here. We welcome your feedback at reviews@hackspirit.com.

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Lachlan Brown

I’m Lachlan Brown, the founder, and editor of Hack Spirit. I love writing practical articles that help others live a mindful and better life. I have a graduate degree in Psychology and I’ve spent the last 15 years reading and studying all I can about human psychology and practical ways to hack our mindsets. Check out my latest book on the Hidden Secrets of Buddhism and How it Saved My Life. If you want to get in touch with me, hit me up on Facebook or Twitter.

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