Last updated on October 5th, 2019 at 06:30 pm

These funny icebreaker questions are for getting conversations started.

I have used this in every situation and every kind of person.

Not all the questions are applicable to all people but there is certainly something for everyone.

You can use them in person, on the phone, in a chat.

Or if you want to use them for fun emails, and surveys questions, please be my guest.

That said, I’ve categorized them into sections so It’ll be easier for you to understand the topic of each question.

Are you ready?

If so, let’s get started as I introduce to you the…

What Will I Learn?

41 Best Ice Breaker Questions of All Time

About the Past


1) What is your earliest memory?

This is of the most fantastic icebreaker questions that many people love asking.

The goal here is to make the person in question think hard.

Although it is quite an interesting question, it’s also incredibly difficult because it requires serious brain power.

Some people, however, shy away from answering because they don’t want to ‘disturb their brain.’

But it’s an excellent question to ask anyway.

2) What did you enjoy about school?

This is one the of questions I enjoy asking and answering the most.

We all enjoy a thing or two about school.

It could be the discipline, friends we made, our teachers, etc.

Very few, if any, would object to this question because it brings out the sweet memories of the past and who wouldn’t want to share his or her past memories.

3) Name one thing you miss about being a kid?


We ALL enjoy being kids.

It was a fun time when you didn’t have to worry about the next meal and stress of getting and securing a job.

One thing I actually enjoy about being a kid is not having to worry about money.

And I know it certainly resonates with you too.

So, this is one of the ice breaker questions that will get things going.

4) Who was your enemy or the bully when you were young?

This is also another funny ice breaker question that will bring out the comedian in the person.

Almost everyone on earth has an enemy or two who is a chronic bully when they were growing up.

I had this huge guy who would wait at the entrance to our school premises to bully on me after school, but I always manage to get my way out.

5) What was your favorite musical group when you were in Junior High School?

This is a fascinating question nonetheless.

It reminds me of a popular music group in my high school days that I refused to join because I was afraid of appearing before crowds.

This question can lead to an invigorating conversion if the person in question did participate in a musical group during his/her heydays.

Else, you may get a shallow response and may have to ask another.

6) When you were a kid, what did you want to be when you grew up?

A pilot, an aero engineer, football or soccer star, doctor, lawyer?

And so on.

The truth is, we all want to become something important when we grow up.

But in reality, 90% never become what they dreamt.

This question, no doubt, will put a huge smile on your listener’s face and trigger a quick and interesting response.

7) What was your favorite childhood injury?


I like this question, and I believe you do too.

Although some may not want to give an answer real quick, when they do, it’s definitely going to be an awesome one because it reveals the deep pains of our childhood.

If you do not get an interesting answer, know that you may have to reword the question to fit your style.

8) When was the first time that you had a beer?

Many of us, I believe, took our first bottle of beer at an almost illegal age.

But it’s all good.

So some may not want to reveal everything and tell you almost the truth.

I’ve asked this question to some persons, and their response didn’t quite satisfy me.

9) Who was the worst roommate you have ever had?


This question kind of reminds you of your funny days in school, right?

Yea, me too.

I didn’t like my roommate because he farts a lot and is very unclean.

I always try to encourage him to keep clean but to no avail.

To this day, he hasn’t changed much either. But that’s for him.

This is a priority-type question.

So keep it on your priority list.

10) What is your worst dating experience?

Be careful when asking this question.

Most people do not like to divulge their painful past experience including me.

So, while asking, do not hope to get an interesting answer but some do actually open up and tell you everything.

Just don’t be 100% hopeful on this one.

You might be lucky and get a soul-rendering experience.

11) Which is the funniest prank played on you or played by you?

We all have that hilarious prank that makes us laugh out our heart.

I could still remember the one played on me back in the University.

It was so funny that I almost fell into a nearby pool of water.

12) What is the craziest thing you have ever done?

There is a lot of crazy things we did while growing up and even during adulthood too.

So get ready to laugh out a bit on this one.



13) Do you have any hidden talents?

Do you?

Some of us do have some hidden talent, but the majority don’t.

By asking this question, you might be able to find out if the person in question is among the fortunate few.

14) What jobs do your parents do?

15) Name one thing that not many people know about you.

This one is going to be uniquely special.

I so love this question and have asked it a couple of times this month.

What this question does is bring out the real side of the person and sometimes the answer may lead to yet another far-reaching question.

Always listen attentively so you can ask pinpointed, viewpoint follow-up questions.

That’s the only way to lit up the conversation like never before.

16) Tell me about a funny family story.

I bet this question will lead to a little exposing of a few family ‘secrets’.

You just have to listen carefully to the answer to this question because you’ll get to hear some little funny ‘dark’ area of the person’s family.

17) You wouldn’t be caught dead, where?

18) Was there ever a time when you were frightened for your life?

I LOVE this question so much.

I’ve asked it a couple of times too.

I will never forget an incredibly frightful incidence in my early teens where I saw a huge snake crawling on my bed at night.

I was just so lucky that I turned on the light before flying on the bed otherwise I may not have had the opportunity to write this article.

So be ready to be WOWed as the answer to the question unfolds.

19) What outdoor activities do you like to do?

There are so many, many outdoor recreations, such as;

  • Trekking
  • Rock climbing
  • Mountain biking
  • Birdwatching
  • Tree climbing
  • Mushroom hunting
  • Water sports
  • Waterskiing
  • Sandboarding
  • Metal detecting
  • Fitness trail

To mention but a few.

18) Where is your most favorite place on this earth?

There are so many beautiful places on earth like Bahamas, Brazil, and even the U.S.A.

I like this question because you’ll get to find out some interesting places on earth you’d never had heard of.

19) Why do you like living in this area?

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

21) What do you consider your greatest achievement?

This can get personal, and I assure you that the answer will put a smile on your face.

Trust me.

22) What is the one thing for which you would most like to be remembered after your death?

23) Do you have any phobias?

We all do.

Mine is mice.

I have a severe phobia for mice.

You’ll be pleasantly surprised that the person’s phobia might the same as yours or might be something you have no fear of at all.

24) Do you feel you have a purpose or calling in life?

Here comes a religiously directed question.

If the person is religious, you might get the most exciting answer ever and sometimes you’ll discover a whole different side of the individual.

It’ll be fun.

25) Name three exotic countries you would like to visit

I’ve visited mine already; Dubai, Bahamas, Qatar.

I enjoyed every bit of my stay in those countries.

You have yours too.

You can also follow-up by asking why he/she likes the countries mentioned.



26) If your house was on fire and you could grab only three things before leaving, what would they be?

Oh, how I love this question.

This is one of the ice breaker questions that’ll life-up the conversation.

I asked this question to my boyfriend during the summer of 2017 and he revealed something I never knew about him.

So get ready to hear a newer side of the person.

What he or she is most interested in.

What he/she values most in life.

Just make sure you ask this question early enough.

27) Do you believe in extraterrestrials or life on other planets?

28) Do you believe in ghosts?

When I asked this question to a couple of my workmates, I was perplexingly surprised that only one person out of the 12 I asked, believed in ghosts.

This is quite surprising because they are all Christians and I started to wonder if truly ghosts exist.

When I dug deeper, it became clear to me that the others do not actually believe what their Pastor says about the ghost.

And that they are not convinced enough that there is a ghost in the real world.

So you may be in for a surprise too when you ask this question.

29) What do you value most in life?

We all have someone or something we value most in life.

For many, it could be their God, Car, House, Wife, Husband, Kids, etc.

You can also ask follow-up questions to dig deeper if necessary.

30) If you were one of two people left on this earth, and the other was the same sex as you; would you go gay?

I don’t like asking this question because I don’t have guts to ask.

But if you’ve got the guts, then, by all means, go for it.

But I have to warn you, the answer may not be interesting but you’ve got to try.

31) What do you think the greatest invention is in your lifetime and why?

For many people (including me), it is electricity and the internet.

Electricity has brought in so many technological inventions that we possibly would never have dreamt about.

The Internet has revolutionized the world and made it a global village.

And I believe, the answer you’ll get to this question would be any of the two I mentioned.

32) What do you think the secret to a good life is?

I for one think that the secret is happiness.

What’s yours?

Let me know in the comment section below.

This is one of the best ice breaker questions I’m yet to ask.

But I’ll make sure I get this going this week.

33) What would be your dream job?


Mine is sleeping and watching movies. LOL!

This is going to be a fun question, and the answer would be even funnier.

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

35) If you HAD to change your name, what would you change it to?

I’m not sure many people would love to change their name to another.
But some would.

The point is, you are trying to get the person to think out of the box and also to ascertain if the individual actually likes the name he bears.

36) If you could live anywhere in the world, where would you live?

The Bahamas, no doubt.

This question is a fantastic one and is sure to ask it early on as well.

37) What is important to you right now?

38) What is your goal in life? Do you think you will achieve it?

39) If you knew you were going to die in 24 hours, name three things you would do in the time, you had left.

40) What crazy activities do you dream of trying someday?

41) If you could go on a road trip with any person (dead or alive), who would you choose and where would you go?

There you have it – 41 fun ice breaker questions to ask just about anyone!

Like I said earlier on, you can use these questions anywhere – on the phone, in person, in a chat – just about every and anywhere.

That said, thanks for reading this article in its entirety.

Let me know your stunning ice breaker questions ever.

Also Read:

Good Questions to Ask a Girl

Interesting Questions to Ask a Guy