To help us get through the last of the winter woes, March has been all about FUN. With spring around the corner, you’ll be getting out and about more which means there are LOTS of occasions to meet new people – which also takes courage. So why not have some fun with it (rather than go in nervous and unsure, like most of us do), while stepping out of that comfort zone?

Below are my Top 10 Most Courageous, Fun Icebreaker Questions to help you get yourself AND others out of their comfort zone and chatting away.


Time Machine Icebreaker Question

1. If you had a time machine, what time and place would you go back to, or ahead to?

Rules of engagement: people would go back exactly as they are, and would only need to stay for a couple days – but that keeps it interesting. For example, not every place in time would be great if you are a woman, for example – so it really ads some diversity!


Superhero Icebreaker Question

2. If you could have any superpower, what would it be?

Rules of engagement: the answer could be pretty much anything except it is a bit of a cheat to pick “having the power to use any super power” so we’d veto that one.


Sports Icebreaker Question

3. If you could be amazing at any one sport, what would it be?

Rules of engagement: this one’s pretty straight forward but if you notice the other person is struggling a bit you might want to help out with a few unconventional ideas or go first even to set the tone (for example, “I always thought it would be cool to bobsled, not luge though – that looks terrifying).


Instrument Icebreaker Question

4. If you could be amazing at any one instrument, what would it be?

Rules of engagement: we tend to position this one as though you would’t actually have to go through the process of learning that instrument – you would just be amazing at it. That can make a BIG difference for people. It can also give you a second question, which instrument would you like to learn!


Travel Icebreaker Question

5. Where is the next place/few places you want to travel to?

Rules of engagement: it’s easy to have a list of 10, 20… even 50 places you might want to go, so try to limit it to 1 to 3.


Live Abroad Icebreaker Question

6. If you could live anywhere in the world where would it be?

Rules of engagement: where to live is somewhat different than where to travel to, so do a little more probing here, find out what it is that appeals to them about the city in a long-term sense (also helps you get a bit of an idea of what they might value).


Lottary Icebreaker Question

7. What is the first thing you would spend money on if you won 50 million dollars?

Rules of engagement: again, people often have LOTS of ideas here so try to limit it to 1 to 3 things. AND if they go for “I’d invest it” – push them for something a little more… indulgent. Perhaps, the first thing they’d spend on AFTER they invest a bunch.


School Subject Icebreaker Question

8. What was your favourite subject in high school?

Rules of engagement: lunch does not count as a subject. Neither does a spare period. They must have had some interested in something, so push them a little bit.


Service Icebreaker Question

9. If you could hire someone to help you in one area of your life, what would it be?

Rules of engagement: here’s we are looking for something like “a chef”, “a cleaning lady”, “a secretary to make my appointments”, etc. A “personal assistant” is a bit of a cheat, but you can get around it by asking more about what tasks they would have that person perform more specifically.


Hero Icebreaker Question

10. Who is your biggest hero/someone you look up to or respect the most and why?

Rules of engagement: while a lot of people may say someone well-known, this can be a friend or family member or someone you don’t know. If so, make sure to try and get a good sense of what that person is like – it’s a great way to get them talking about someone who means a lot to them too.


Well, those are some of OUR favourites but you probably have some too so feel free to post about them in the comment section, at or by tweeting them at @couragecrusade.

And make sure you have a lot of FUN using them folks!

Have a courageous day.

Learn more about The Courage Crusade at