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 in and grill 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 20 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 stand alone 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?

In Conclusion

Regardless of where you are in your relationship, asking questions of one another is a great way get to know someone, keep tabs on where you are at in life, and continue to discover things that you may have in common.

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.

After all, two days in a row are never the same. So ask questions and listen for the answers and you and your guy will continue to have a great relationship for years to come.

Encourage him to ask you questions as well, and always follow up with additional questions to keep the conversation going.

There’s always something to learn about your significant other, so give this a try when you are feeling like you might be stuck, or you want to shake things up over dinner tonight.

A quick message from Lachlan Brown, the founder of Hack Spirit

In 2018, the third year of Hack Spirit, I poured thousands of hours and considerable resources into creating these articles. It's a labor of love and remains free thanks to your patronage. If you found any value in these articles, please consider supporting what I do with a donation. Your support is what helps me to continue creating more Hack Spirits articles. To make a donation, click the "donate" button below and choose between a single donation or monthly.

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