Last updated on October 5th, 2019 at 06:14 pm

Are you seeking for the right questions to ask a guy you’ve been crushing on for a long time?


Do you really want to get to know more about a guy you like?

If your answer to the questions above is YES!,


Stay tuned!

Because I’m about to hand over to you my all-time 20 interesting questions to ask a guy that’ll make him like you almost instantly.

You see, many girls find it incredibly difficult to start up a conversation with a guy they like or have been crushing on for a long time.

It’s happened to me several times.

But I overcame it with the help of questions.

And when I say questions, I mean the Right Questions.

So let’s get the ball rolling right about now.

Are you ready?

20 Good Questions to Ask a Guy to Get to Know Him Better

1) Mention three things you consider yourself to be very good at.

guy skateboarding

First things, first.

This is a fantastic icebreaker question.

It is always the first question I ask a guy.

It’s important because it makes you understand what he is good at and that can go a long way in helping you understand some of his personalities and passion.

You simply cannot go wrong on this one, trust me.

Try it!

2) What kind of puppies do you hate the most?



I so love this question because I personally don’t have much love for the Australian Shepherd as I do for the Siberian Husky.

I know it’s slightly weird, but that’s how it is for me.

I love the Australian Shepherd so much, and that’s how it is for some people including you.

Also, make him explain why he doesn’t love a particular puppy.

This is really a cool question to ask any guy.

3) If you had to eat a pigeon…how would you cook it?

guy cooking


This question might be the last one to ask, girl.

It’s a funny one, but I find it one-sided – You know what I mean.

Yea it’s because some guys do not like eating pigeon.

I know so many of them.

But you never can tell.

He might be a pigeon eater.

And if he is, girl, you’re in for the hilarious moment of the conversation.

I tell you, you’re going to crack your rib on this one if he doesn’t know how to cook it properly.

4) Have you ever won a trophy?

guying lifting uo trophy

Guys are generally ambitious.

Most are sports lovers.

So this question is spot on!

7 out of 10 guys will most likely have won a trophy or two before 30.

Either as an individual or a group.

So get this going and make sure you ask to follow up questions too.

5) What jobs do your parents do?

man working

Pretty simple question to ask a guy.

He’d be more than willing and happy to answer this right away.

Who wouldn’t want to share some family story?

So this is an excellent question to ask.

You can even ask this question first if it pleases you.

But I’ll leave it to you.

6) What’s your favorite father moment?

man happy

Another family question.

This should be more of a follow up from the previous question than a stand-alone question.

So only ask this question when the previous one was about his family.

It’ll get the conversation going smoothly, and you’ll actually enjoy his answers, trust me.

The next question will get conversation blistering with a smile.

7) What family member are you really proud of?

guy congratulating brother

We all have that family member that we are incredibly proud of.

So this a fascinating question to ask a guy and one of the best.

This type of question can make the conversation a memorable one, and he’ll forever cherish this moment.

Also, make sure you ask a follow question in the lines of; Why are you proud of him/her (that is, his family member).

8) What did you enjoy about school?

guy at school

For most guys, it is the friends they made, a trophy they won, connections, etc.

There are just so many things we enjoy about school.

So I’ll give this question an 8/10.

Simply a fantastic one to ask.

It shows that you care about the guy’s past and he’ll like you for that.

9) As a child, what did you want to be when you grew up?

kid thinking


Another funny question.

So many of us ended up doing an entirely different thing from what we dreamt of when growing up.

But that’s life.

Only a few actually got what they wanted and kudos to them.

And if you’re one of those, double kudos to you.

This question could get a little emotional answer if the guy’s past were rough and painful.

But you’re going to enjoy the answer, no doubt.

So, onto the next one…

10) Which is the best vacation you’ve ever had?

guy on vacation

Vacations are always memorable.

The opportunity to get out of your environment, make new friends, refresh your life and brain, meet new people, and see the world in a different angle is something we all love and look forward to engaging ourselves in.

Everyone on earth including you love vacation.

I super love it!

So this question will bring the interesting, humorous side of the guy.

11) List one thing you wish you could change about yourself.

man looking at the mirror

We are all imperfect, and sometimes there are things in life we’d wish to change.

The same goes for the guy you like.

Be careful on this one though because it is a pretty personal question.

But, believe me, 9 out of 10 guys would be more than willing to tell you straight up without muffling and mumbling.

12) Who would you turn to if you were in desperate need of help?

guy praying

A majority would say God on this one.

So I think this question is actually an indirect way of knowing his stance on religion.

This is really vital, and I’d say it’s one of the most important questions you can ask a guy.

Very Important!

Because religion plays a huge role in the lives of some guys and you’d want to know what he believes in and why.

Also, make sure you ask follow-up questions.

It’s incredibly necessary here.

13) If you could change the world what would you do?

guy think about the globe


I’d say this question is the most important of them all.

I like to know how my man views the world.

  • Is he affected by the tragic events happening all around the globe?
  • Does he care about making this world a better place?
  • Is he a reasonable type?
  • Does he have feelings for people suffering and struggling just to get a meal/day?

These are the questions you want to be answered.

So make sure that as you ask him this question, his answers satisfy the questions above.

14) Which would you rather have, $50,000 or true love?

money or love


This is a very funny but tempting question.

I know of some guys who’d go for the former.

They’d tell you that money can be true love.

We all know that’s not true.

So this question is about finding out his interest in material things.

  • Is he over materialistic?
  • Does he value money more than anything else?

You’ll get the answer to those question when he’s finished talking.

So make sure this question is in your priority list.

15) What do you consider the most important event of your life so far?

guy at an event

This is a pretty basic question but also an important one at that.

You must ensure that you ask follow-up questions such as one the following;

  • Why is the event so important in your life?
  • What lessons did you derive from attending the event?
  • Has the event changed your perspective in life in any way?

There so many follow up questions on this one but make sure you know what you’re asking.

One fantastic thing I like about good conversation is that you just have to get started and the follow-up questions will flow naturally.

It’s that simple and easy!

16) If you could have three wishes granted, what would they be?

guy thinking hard

The following should be on top of his list I guarantee you;

  • Lots of money
  • Big house
  • Nice Cars
  • True love

I’m very confident about this because those are the answers I got when I asked my crush back then now my lovely boyfriend.

So you can’t go wrong with this.

This is also a pretty good avenue to find out what’s essential in the life of the guy.

What he cherishes and values the most in life.

It can truly bring out some of his innermost thoughts and girl; this is what you want.

17) Do you believe everything happens for a reason?

guy looking and thinking

Also, a religiously-angled philosophical question to ask a guy.

But it’s an excellent one to ask.

I tell you, you’ll get to hear some weird and intriguing answers to this question.

People see the world in a different way than you and me.

So this is a lovely way to get to know the guy better as to how he views humankind and the world in general.

18) Do you believe in ghosts?


I don’t.

How about you, do you believe in ghosts?

Well, this is also a religious question too.

I like asking this question a lot to guys because they tend to be very afraid of ghosts even more than we girls.

Don’t ask me why because I can’t prove it.

But that’s how I feel though.

The truth is, this question will get you to understand some psychological makeup of the guy, and it’ll go a long way in helping you know if the guy is the right person for you or not.

Make sure you ask some follow-up questions because the initial would usually be one word – Yes or No.

19) If you had an unlimited shopping spree at one store, which store would that be?

guy shopping


My boyfriend said Walmart!

And I burst out in laughter.

He loves electronic games too much!

I was even beginning to worry if he loved his game more than he loves me.

In fact, it got to the point that I actually asked him.

But my worries were later quenched that day.

So you see, this question can bring out so many things about the guy you like and trust me, every guy on earth would love to answer this question with so much passion and energy.

You’ll love the answer!

And now to the final question on my list…

20) Where do you see yourself in 5 years?

guy thinking about future

Future. Career. Life.

We always think about what the future holds especially for the guys.

There is a certain age a guy would get, and the society would start expecting him to have attained or achieved a particular thing.

Very common in places like Africa, the Middle East, India, and even Europe.

And I also know this question is asked in a lot of job interviews nowadays,

You’re not interviewing him or something like that.
You’re just trying to find if he cares about the future.

  • What is his goal in life?
  • How does he plan to attain or achieve?
  • Is he working towards it?
  • How hard is he willing to go the this accomplished?

Great questions that are begging for answers.

So by asking the question, you almost always get answers to the viewpoint questions I listed.


So that was it! – 20 Good Questions to Ask a Guy.

I hope you enjoyed reading it.

And thanks for perusing it in its entirety.

On a Final Note…

The right questions are very critical when you want to get to know a person better.

Ensure you don’t just copy my questions word for word.

You can if you like.

But I’d really love it and encourage you to tweak them to a more personal tone.

To fit the guy in question.

And always, always, always ask follow-up questions.

The truth is, follow up questions on a particular question on here would be all that you’ll need to get to know him better.

I’m talking out of experience.

So in all that you do, ensure that your motive of asking the questions is pure.

So that is it, babe.

Go have fun with your guy!

Further Reading: 21 Good Questions to Ask a Girl to You Like